The Florida Keys and Key West

Keys Map with Key West

The Florida Keys and Key West

There are probably a couple dozen famous cities in the world that everyone either visits or wants to visit. Typically, Paris, Moscow, New York, Hollywood, Tokyo, Singapore, Hong Kong, London and a few others come to mind. But none compare to the worldwide eclectic reputation of Key West. The proliferation of cruise ships pulling into Mallory Square every day in the last pre-pandemic years has made Key West an international destination of some repute!

Unfortunately, few people see the REAL Key West the way it should be seen. Walking Duval Street from one end to the other is a good start, but that jaunt does not do much for the history, novelty or uniqueness of the island. There are dozens of things to do in Key West – you can’t get bored!

Key West Southernmost Buoy

The most photographed place in America.

Sure, Sloppy Joe’s sees all the tourists, but there are more bars and restaurants just as entertaining, just as quirky, and way less “touristafied” (we just made that word up!) than Sloppy’s.

Everyone knows the Southernmost Point big red marker, but there are many other symbols around town much more interesting. Everyone seems to gravitate to the sunset celebrations at Mallory Square each evening. There are some beautiful sights all day long. You don’t have to wait for sunset in Key West.

There are three modes of transportation that bring most people to Key West –  automobile, plane, or they come by boat! We aren’t going to waste too many words on planes and boats. The most fun getting there is by driving US Route 1 through what we call “The Keys”. Keys are islands that populate southern Florida as they protrude out into the Gulf of Mexico to the north and the Atlantic Ocean to the south.

Few highways have more allure than US 1 in the Keys.  Places like Key Largo, Seven Mile Bridge, Hawk’s Cay Resort, the sports fishing capital of the world, Islamorada, are all along this famous road. All of these famous places have international reputations for different things and all are on the only road to Key West.

The end od US 1 - Mile Marker Zero!

The end of US 1 – Mile Marker Zero!

Once we arrive in Key West we have details and some adventures for about three days and nights of things to do in Key West. Why THREE nights? Well, our experience is that any more than three evenings in Key West, and the Betty Ford Clinic starts to sound really good!

The good news is the Florida Keys are a must visit if you are driving to Key West. You don’t have a choice. It’s the only way to get there.

The fun begins when you enter the islands. From Key Largo to Key West is the ultimate Florida road trip. There are 44 islands and 42 bridges between Key Largo and Key West. We never counted. Just savored every moment of the many trips we have made.

As we suggested, getting there may be half the adventure!

US Route 1 – The Only Route to Key West – Things To Do in the Keys

It doesn’t matter if you drive south from Minnesota, Maine or Miami. You end up on one single road that delivers you from everyday life into a glimpse of paradise! The

The 100-mile journey begins in Key Largo. But US Route 1 runs 2,369 miles from Fort Kent, Maine to Key West, Florida. The only way onto the islands leading to Key West is by the federal highway US 1 just south of Miami in Florida City. US 1 leads directly to Key Largo. A collection of bridges will have you crossing more than three dozen other

Caribbean Club Key Largo

Caribbean Club where Bogart and Bacall made history.

islands before the last island of Key West.

But stop – we already are going to take you on a detour! About a mile out of Florida City you will see a road sign directing you to Card Sound Road veering off to your left going south. Take it!

Now a word of warning, if you are close to being out of gas, try it next time. If you don’t like odd drives along varying waterfront wilderness, keep going straight. If you don’t

Picture Caribbean Club Key Largo

Picture on wall at Caribbean Club. Movie Key Largo.

like old Florida dive bars with a name like Alabama Jack’s, don’t bother. Just stay on US 1 if you aren’t adventurous – both Card Sound Road and US 1 eventually lead to Key Largo!

Alabama Jack’s appears about ten miles into your drive to Key Largo on Card Sound Road. It’s a favorite of locals, travelers, bikers, boaters and other characters willing to take an extra 15 or 20 minutes to get to the Keys the fun way. Jack’s is a waterside bar serving refreshments you will probably need as you enter paradise. The food is average bar food. The beers are cold.

At Alabama Jack’s you can look over the rail and watch mangrove snapper feeding along the pilings the restaurant is built upon. This stop represents the rest of your trip – a whole lot of different people just enjoying being where they are, with no color lines, no status lines, no age lines, no gender lines – just people at the beginning of a great journey.

A sunset over a body of water next to a palm tree Description automatically generated

Sunset at Reefhouse Resort Key Largo.

As you leave Alabama Jack’s you will continue southwest on Card Sound Road. Eventually, you will enter US 1 again at the northern edge of Key Largo.

At this point, we need to explain about mile markers. They will help you find everything along the road to Key West. You will see your first marker around number 106 as you enter Key Largo. You have 106 mile markers ahead of you – enjoy it!

Skippers Key largo

Tiki Bar at Skippers, Key Largo on the canal.

We will make a note that at mile marker 104.1 you will see a sign for the Caribbean Club. If you are thirsty again, you might make a stop here. Their claim to fame is the 1948 old movie Key Largo was partially filmed here. Humphrey Bogart may have shared a bar stool with you here. The Caribbean club could make our list of the top dive bars in Florida.

On down the road at MM 104 is a better stop if you like tiki bars. Jimmy Johnson’s Big Chill serves some rather good food and has a huge tiki bar built over the water on the Florida Bay. If you don’t recognize the name, Jimmy Johnson is the former coach of the Dallas Cowboys.

John Pennekamp State Park Key Largo

John Pennekamp State Park is unique – most of it underwater!

If you are looking for a place to stay before you complete your journey to Key West, the Reefhouse Resort & Marina (formerly the Marriott Resort) at MM103.8 is excellent. The Reefhouse’s sunset bar, Breezer’s’ is a fabulous place for appetizers and watching the sun creep into the bay. The sunset photo above was taken from the landing at Breezer’s.

A mile down the road is the entrance to John Pennekamp State Park. There is a plethora of state parks in Florida and several along your way to Key West. What makes this one different is that 75 square miles of it is underwater! There are trails and things to see on shore, but this park is made for snorkelers and divers. It’s worth the stop and the dive for an underwater surprise we won’t spoil here!

Wild Bird Sanctuary

The Wild Bird Sanctuary does great work preserving the Keys wildlife.

By the time you get to MM (mile marker) 100, you may be getting hungry. If so, look for Skippers Dockside. It is a little off the main road, but the food is better than average. Try the shrimp ceviche for a good Florida appetizer. Docked on Skipper’s inlet is more Humphrey Bogart film memorabilia. A replica boat featured in the film The African Queen takes people for tours.

Back on the road, you will enter the next island town, Tavernier, Florida. At MM 93.6 is the Florida Keys Wild Bird Center. The people here do great work rescuing birds who have been injured or entangled by fishing line or nets. You can see numerous species in the sanctuary rehab center. A kindly donation would help preserve the Key’s wildlife.

Oceanview Sports Pub

Oceanview Sports Pub is owned by a former Pittsburg Steeler.

We must insert a note about things to do in the Keys. The drive along US 1 has all kinds of attractions, sights, unique shops, and places you may want to see. The ones listed here are just a few recommendations along the way. The trip has over 100 miles of scenery! If we listed every interesting site and attraction, you would not get to Key West until the following week. We are pointing out a select few to make the drive interesting. If you want a detailed mile-by-mile guide,  follow this link.

At MM 84.2 you will see a big sign

Theator of the Sea Islamorada

Theater of the Sea Islamorada is a place to learn about sea life.

advertising the Theater of the Sea. Try to plan a visit. The Theater is just that – a tropical stage to interact with dolphins, sea lions, sea turtles, fish, sharks, stingrays, alligators, and birds. The surroundings are a lush tropical setting for learning about Florida aquatic wildlife. It’s a fun and educational couple of hours.

Theater of the sea islamorada

Amazing what dolphins and other mammals can be taught.

Islamorada – Sportfishing Capital of the World

If you have observed, the signs will be telling you the city you are in is Islamorada, the sport fishing capital of the world. On the right side of the road (north) is Florida Bay (part of the Gulf of Mexico). The Bay is an estuary for many saltwater species including tarpon, bonefish, mangrove snapper, redfish and snook. On the left side of the road (south) is the Atlantic Ocean. A few miles offshore, fishermen from all over the world angle for sailfish, marlin, swordfish, wahoo, kingfish, grouper and yellowtail snapper, to name a few of the available trophy fish.

Tiki Post Card Inn

The new tiki bar rebuilt at the Post Card Inn

As you leave the Theater of the Sea, just ¼ mile down the road is the Post Card Inn. The reason the Post Card is significant is the huge fleet of fishing charter boats anchored at their very new marina. Another reason and the Inn’s recent recovery and re-building.

Hurricane Destroys Post Card Inn

A little history. While the Keys are known for their beauty and tropical weather, they also are known for their hurricanes. In 2017, Hurricane Irma hit this part of the Keys with a vengeance, destroying the Post Card Inn. The INN remodeled, rebuilt and restored the entire property. Thus, the new marina, new tiki bar and an ocean front hotel worth spending a few hours or a few days. They also built a new ocean view fresh seafood bar overlooking the Florida straights (Atlantic Ocean).

Worldwide Sportsman

The Worldwide Sportsman is an outfitter for all types of water sports.

Note: You will hear more about the effect of hurricanes much worse than the one in 2017. The Keys are resilient, if not defiant, when it comes to the weather.

While the Post Card Inn is one of our many favorites, there are dozens of marinas, hotels, resorts, restaurants and boat dealers along your journey. On some of the back roads along the way are very quaint bed and breakfast retreats as well as some old fish camps.

Hurricane Memorial

The 1935 Hurricane memorial for the 400 plus people who lost their lives is in Islamorada.

Bridges along US 1 connect the major islands. There are about 1700 islands in the Keys and just a few dozen bridges. Obviously, most islands are not connected by roads. The outlying islands are a vital part of the estuary of the Keys.

One bridge that is very special is heading over to Matecumbe Key at MM 77. Just at the base

Feeding Tarpon at Robbie's

Feeding Tarpon at Robbie’s can be a little daunting with your hand that close to a 200-pound fish!

of the far west end of the bridge you will see a big sign that says ROBBIE’S. Robbie’s has become a major attraction for travelers in the Keys. Thousands of people stop to hand feed tarpon that weighs more than most teenagers! Make Robbie’s one of your things to do in the Keys.

Robbie’s also has a collection of little tent stores that sell everything from baubles to beads and everything from “Florida” (but mostly made in China!). This is an obligatory stop for the traveling tourist (at least once) to feed the tarpon. If you have kids from 5 to 105, they will love it!

On down the road about ten miles, at MM 67.5, is the Long Key State Park. What a great

A resort near the water Description automatically generated

Hawks Cay Resort is a sportfishing and family oriented resort.

place to hike, swim, camp or just stroll around the park. This is one of Florida’s many state parks that is unique because of the Atlantic Ocean view! Who doesn’t want a picnic viewing the Atlantic Ocean?

Before you get tired of walking the ocean side, save some energy for one of the most famous fishing resorts in the world. Hawks Cay Resort is at MM 61.1. If you have ever watched any outdoor fishing shows, Hawks

Dolphin Research Center

Dolphin Research Center

Cay has been featured many times showing the bounty of nearby waters.

Hawks Cay is a place for good old-fashioned family fun. The resort has every possible saltwater activity, with the focus on sport fishing. The kids will have fun too with a huge pool, paddle boards and daily activities. The food is exceptional, so lunch on the way down the Keys at Hawks Cay is a great stop.

If you have kids, 5 to 105, The Dolphin Research Center at MM 58.9 is the place to go. This facility is for family fun and they do great work to preserve our dolphin population. They have a research center and a large contained area in Florida Bay where they rehab and train dolphins. The kids love it (and adults too).

Crane Point Marathon Florida

Crane Point in Marathon is a place to see how people lived in another century.

One big development just before you get to Marathon is Key Colony Beach at MM 54.  This is a community with over 400 homes on a large peninsula out in the Atlantic Ocean. Few communities exist in the Keys of this size. A quick drive-through might be an interesting glimpse of how people live in this part of paradise! As a side note, much of Key Colony Beach was destroyed by a hurricane in 1960. It was redeveloped into the city of about 800 people it is today.

By the time you get to MM 53.5, you will be in Marathon, Florida. A city of about 8500 people stretching over several keys (islands), Marathon is known for (of course) fishing, the second largest airport in the Keys, and most of all being halfway to Key West! Notice the many shops, restaurants and businesses with names that start “Halfway….”. There is Halfway Cleaners, Halfway Cafe, Halfway Barber Shop, Halfway Pizza, etc.!

Perhaps the most interesting place of all the things to do in the Keys we discuss is at MM 50. Crane Point Museum and Nature Center is one of the coolest places to find out about the Florida Key’s history, nature and early life in the islands – all in one place!

Crane Point is a privately operated attraction that offers exceptional opportunities to see and feel how it must have been to survive on this strip of land a couple hundred years ago. Of the nature trails on these 63 acres is one that leads to the Adderley House. This home was built about 1903 from materials found around Vaca Key. It survives today to remind us of the hardships faced by our forefathers. Make time for a couple hours here – it’s worth the visit!

7 mile bridge Florida Keys

They call the 7 mile bridge the 8th wonder of the world. We just call it awesome.

Yes, we are just halfway to Key West and some of the best traveling is yet to come! In fact, you will see in the next three miles places like the Stuffed Pig, a great little local’s place for breakfast and lunch, and then you will start seeing signs like the 7 Mile Pizzeria and the 7 Mile Bar & Grill – heads up! You are coming to the most spectacular views on your entire trip – The Seven Mile Bridge!

Half Way To Mile Marker Zero

The current Seven Mile Bridge was completed in 1982 and was one of the largest bridges in the world at that time. Alongside the new bridge you will see the remnants of a bridge Henry Flagler completed for his railroad in 1912.

Flagler Bridge

The remnants of Henry Flagler’s bridge runs parallel to the 7 mile (what is left of it).

Built against unbelievable odds and at the cost of a major portion of his fortune from his Standard Oil investments, Flagler’s railroad bridge helped to build much of the lower keys. Flagler’s bridge brought tourists and products to and from Key West leading to twenty-plus years of prosperity.

That is prosperity until the Great Labor Day Hurricane of 1935 destroyed the bridge structure. In the face of this destruction, the United States bought the right of way from the railroad and made a bridge for automobile traffic from the remaining structure. The back story and history of the bridge is fascinating, but the real story is in the spectacular views on both sides of the bridge.

Key Deer Big Pine Key

Key Deer on Big Pine Key are about the size of a large dog. A unique species to Florida.

Florida Bay on your right and the Atlantic Ocean on your left makes keeping your eyes on the road nearly impossible. You will see ships on the horizon in the Atlantic and bay fishermen looking for snook and tarpon in the shallows. The sparkling blueish-green water laps the pylons of the bridge along with the waves produced by the boat traffic underneath. Sunrises and sunsets are breathtaking! Seven miles is a long way to travel on a bridge, but the time seems but a small few minutes you hate to see end.

After about 7 miles (imagine that, on the seven-mile bridge), the bridge comes to an end! By now you are awestruck with the beauty of the Florida Keys.

But as hard as it is to imagine, at MM 36.8, get ready for a whole new close up experience at Bahia Honda State Park. Yes, this park has all the normal things state parks have, hiking, camping, swimming and more. But Bahia Honda offers a unique chance to get in the water and snorkel over the shallows to see another whole world beneath the surface of the ocean.

Bahia Honda is a family favorite due to the relatively shallow water and the ability to give children more than a cursory education about marine life. Relax and look around, your next

Bahia Honda State Park

Nice beaches, campgrounds and shallow water snorkeling highlight Bahia Honda State Park.

adventure may just be underwater! Our family tells stories about their first encounters with the creatures of the sea, and their childhood memories as they became acquainted with the saltwater environment at Bahia Honda.

Sadly, we must move on since you can almost taste the margaritas in Key West an hour or so away.

Across the bridge going south you will start seeing warnings about one of the strangest animals in the Keys – the Key Deer. These dog-size animals can be seen day or night on Big Pine Key. They look exactly like their full-sized white-tailed cousins in the woods of the Midwest but are just about one-third the size.

The Key Deer is an endangered species and live only in this area. Their biggest enemy is man and the cars they drive. That is why speed limits are reduced. You must keep a watchful eye out for the deer on the island.

No Name Pub - Big Pine Key, Florida

No Name Pub on No Name Key.

While you are on Big Pine Key, and if you aren’t late for happy hour in Key West, you may want to set your GPS for another out island where the No Name Pub resides. This is a dive bar that has become an institution by selling the idea they are an old bar littered with thousands of dollar bills covering every imaginable inch of their walls. I admit it is a sight to see, but the sight is short-lived once you get on down the road to Key West with dozens of quirky bars!

No Name Pub Big Pine Key

Dollar bills line the walls at the No Name Pub.

If you need to make a stop somewhere you may want to try Boondocks around MM 27 or Mangrove Mamas on down the road, but you are now just about 20 minutes from Stock Island, which we consider part of Key West.

There are a few bars, a naval air station and a couple sights along the way, but few people can bring themselves to stop when they know the excitement of Key West lies just minutes ahead. We entertained you with thigs to do during your drive to Key West….Welcome to Key West

AND NOW  THE ADVENTURE  JUST KEEPS GETTING BETTER …..

FINALLY, KEY WEST – THE SOUTHERNMOST CITY IN THE US

We have been to Key West at least 30 times. We haven’t always driven, but time allowing, we would prefer the drive. We try to cross those 42 bridges at least a couple times annually.

No matter how many times you look out that windshield at that final little bridge over a canal that separates Key West from Stock Island, your level of anticipation peaks at a new level.

We always wonder, what has changed? Something always changes in Key West. Is there a cruise ship in town? Not as many as there were when cruise ships were allowed to go to Cuba.  Any new bars? There are always new bars! Any old favorites closed? There are always a few that close! That’s Key West – the more it evolves, we find that the evolution really doesn’t change the Conch Republic.  END

Airport right beside the baggage retrieval conveyor! A Rum Runner while waiting for your bags is not all bad – welcome to Key West…… 

The images below are iconic Key West – including the real Irish Kevin!

Key West Becomes Conch Republic

The local’s created the name Conch Republic for Key West when residents got tired of federal custom’s officers blocking traffic to the island. The government claimed they were looking for illegal aliens, but Key West residents swore it was drugs they were looking for.

One day in 1982, the mayor and a few of his cohorts decided the city should secede from the United States! They declared the secession, called the new country the Conch Republic, marched to the naval base, declared war, surrendered immediately to the naval commander in charge and subsequently demanded one million dollars in reparations. All in one afternoon before happy hour!

Well, we don’t think the rebels got

Conch Republic Flag

The conchs actually had their own flag.

the money, but they did get the attention of the international media which caused enough pressure on officials to stop the road blocks. That’s how the Conch Republic got its name!

This article is about the REAL Key West. The people, the places, the habits, the oddities – we will try to cover it all. But Key West has a way of re-writing events and history in their own way, in their own time frame!

conch train key west

We recommend a train tour to get your bearings in Key West and to save time.

Nothing ever changes except for the fact that everything always changes in Key West! Its just that no one seems to care or pay much attention.

First time visitor note.  While we will be suggesting the restaurants, watering holes and things to do in Key West, the streets can be confusing. We highly recommend taking a Conch Train Tour if it is your first visit. In an hour you can see the location of every major attraction and get the street layout at the same time. The tour will save you hours of wandering the streets from one end of the island to the other.

There are a dozen different places you can catch the tour train, but the easiest way to find them is to look for 0 Duval street (also location of the Pier House and Ocean Key Resort). If you can find the beginning of Duval, you will see the train!

The Bars, The Attractions, The Restaurants, The Places to Stay

The first thing you need to know is there are about 190 bars on this two-mile by four-mile island – that’s about four times the number of churches – and that’s Key West!

Blue Heaven Key West

The Blue Heaven in Key West is the most famous for breakfast.

Picking the best bars becomes an occupation for some residents of Key West and an obsession for visitors. You can break “best” down into two categories – ones you have visited and ones you haven’t! We are not convinced there is a BAD bar on the island – just different.

Blue Heaven

Be prepared! Blue Heaven has chickens in the trees and everywhere else!

For our purposes we will divide them into two categories – TOURIST’S MUST SEE and OFF THE GRID LOCAL’S FAVORITES.

Tourists Must See Bars and Restaurants

There are bars in Key West that have a worldwide reputation. Your friends, neighbors and relatives might think you were strange if you didn’t visit the basic watering holes! At the top of the list is world-famous Sloppy Joe’s. One door away on Duval Street is Irish Kevin’s, where their irreverence isn’t a place for kids or delicate ears. North a couple blocks is the Hog’s Breath Saloon.

Just west of Sloppy Joe’s on Greene

Captain Tony's Key West

The original Sloppy Joe’s was at Captain Tony’s location.

Street is the original Sloppy Joe’s, now called Captain Tony’s. It is legend that Sloppy Joe Russell, Ernest Hemingway and some other bar slugs moved everything one night in 1937 from the Captain Tony’s location to the current location a half block away. The landlord wanted to raise the rent a dollar a week!

A few years ago we would not have

Green Parrot Key West

Green Parrot has some of the best music in Key West.

Guitar Green Parrot

This guitar hangs on the wall at the Green Parrot. It is signed by some great artists – Joe Walsh, Eric Clapton, Slash, Bruce Springsteen and many more.

included The Green Parrot on Whitehead Street in this list, but they have commercialized their quirkiness to the point you can’t even find a seat anymore. Plus, we used to have to step over a dozen lazy dogs before the health department clamped down on their afternoon dog naps in the middle of the floor. The Parrot generally has some good nightly music.

The Half Shell Raw Bar also became super popular when the Key West Express started dumping hundreds of tourists off at their doorstep over at Key West Bight Marina. The Key West Express is a fast charter boat shuttling

Irish Kevin's Key West

Irish Kevin’s Key West is irreverent as always.

hundreds of passengers a day from Ft. Myers and Marco Island.

Of course, the guy who helps make Key West famous has a place right in the middle of Duval Street – Jimmy Buffet’s Margaritaville! A couple blocks south of Margaritaville is La Te Da. Perhaps, the most famous drag queen performances in the country go on at La Te Da several nights a week and they have their own hotel nearby.

Half Shell Raw Bar

Half Shell Raw Bar is great for fresh clams and oysters.

And finally, Rick’s complex of  three bars on Duval includes Durty Harry’s, The Tree Bar and Rick’s are all great places to people watch. Our favorite is the little dozen seat Tree Bar since it’s directly across the street from Sloppy’s and Irish Kevin’s. The sights are better than an Oscar winning movie!

Off The Grid Local’s Favorite Bars

This list will include some names that could be in the category above. For the most part they are a little more off the beaten path, eclectic (a nice word for a dive), or very different in their own way.

At the top of this list is a patch of gravel-covered ground on the waterfront at Key West Bight Marina. A half dozen dilapidated

Michael McCloud - Key West

McCloud is an example of a guy who came to Key West and never went home!

structures they call the Schooner Wharf. How can you have a falling down bar for 30 years, and it is still falling down, and looks the same through numerous hurricanes and other calamities? The locals at the Schooner don’t seem to care much what it looks like. One thing that makes the Schooner unique is a guy called Michael McCloud.

Michael is listed on Google as an American folk singer, but in Key West, Mike is a legend that started his career at The Bull (another of our favorites described below) 30 years ago. Michael has been entertaining at the Schooner for at least the last dozen years. Despite the look and gravel walkways, Schooner has a darn good burger too!

Shots and Giggles Key West

Shots and Giggles Key West is a local’s hangout we love.

Shots and Giggles party

A group of young ladies celebrating a 21st birthday at Shots and Giggles.

Moving towards Duval Street from the waterfront, take Green Street about 3 blocks west to a relatively new place called Shots and Giggles. Open a few years, my understanding is the bar is owned by locals who wanted a place for their friends on the island. He opened in an old house that is cozy (and small), friendly to dogs (they keep dog snacks handy), even friendlier to people, and clearly not a tourist trap for the fanny pack crowd!

Once you get to Duval Street at the next block, take a left at Sloppy Joe’s. You will walk by Sloppy’s and Irish Kevin’s to Caroline Street which is a block south. There, on the west side of the street is a three-story building that houses three establishments – The Bull, Whistle Bar and Garden of Eden.

We saw a review on a website saying this building was great because they have three options in the same building. That may apply to some people, but a person with a body like mine has no business in the clothing-optional Garden of Eden!  However, my favorite place for people

The Bull Key West

This tree story building hosts three unique bars, including The Bull.

watching is The Bull on the lower level. Big open windows the size of a garage door right next to the sidewalk on Duval Street. You see it all walking by. Remember, you can become part of the street scene if you keep drinking the cheap margaritas The Bull serves.

If you are able to walk a few more blocks south on Duval Street to Eaton Street look for an alley before getting to Southard Street. In that alley will be another local’s place called Mary Ellen’s Bar. This place is not for your children or your 80-year-old mother-in-law who is going to judge you! It is just a back-street bar that has a ton of locals who find some curious ways to promote their evening events. The people in Key West are fun-loving gagsters and this place is an example.

We hate to even publicize the next place! It’s very small, already full of locals, regular travelers and city

Chart Room Key West

The Chart Room Bar is small. This group took up half the room looking for free hotdogs and popcorn.

leaders who used to make their plans over a cocktail or two at the tiny bar. We call it The Peanut Bar, but the real name is The Chart Room in the Pier House Hotel.

The funny thing is The Pier House website lists this as a dining option – the only things they have ever served in The Chart Room were free overcooked hotdogs and some stale popcorn! However, you can help yourself to some peanuts to shell and throw on the floor along with plenty of scuttlebutt from the locals who make this a regular stop.

The Restaurants and Food

Most of the bars mentioned above aren’t known for their food. Sloppy Joe’s is a slight exception since they serve Key West pink shrimp. These shrimp are only found in certain deep waters around the Keys. The pinks have a mild, sweet flavor and a pink shell. Once you have tried them, you will know the flavor. Many restaurants serve Key West pinks, but ask to be certain.

Key West Pink Shrimp

Key West Pink Shrimp – Notice the distinctive darker circle on the back third of the shell.

For the best formal food on the island, there are only a couple places we note. Louie’s Backyard at the south end of Duval Street, near the southernmost point is our favorite. Louie’s has been serving Caribbean style entrees for over 50 years. The restaurant is in an old Victorian

Louie's Backyard Key West

One of the best restaurants in Key West, Louie’s Backyard.

home with a magnificent ocean view. I am told the same award-winning chef has been there for 30 years.

On the other end of the island at Key West Bight Marina you will find A&B Lobster House. Not many restaurants can say they have been

A&B Lobster House

A&B Lobster House serves some of the best seafood in the Keys.

around since right after World War II, but A&B has been serving exquisite seafood for that long. They overlook the marina and offer white tablecloth service nightly. Reservations are recommended.

Sunset Key – Latitudes – A Special Place

Sunset Key Key West

Latitudes on Sunset Key is the best restaurant overall experience in Key West.

There are times when a good or even a great restaurant is not good enough! There is an island across from Mallory called Sunset Key. On the island is a restaurant called Latitudes. The only way you can get to Latitudes is a 10-minute boat ride from in front of the Opal Resort.

If you are fortunate enough to get a reservation, the food is superb. The restaurant is Caribbean luxuriously appointed and service is impeccable. Of course, you are going to pay for the atmosphere, boat ride and 5-star service.

If you can go for a sunset ride across, the lights of Key West and the island lights combine for a memorable trip. Truly a place for that special occasion.

If you want good basic bar food that covers all the bases, try Jack Flats in

Chickens Key West

This chicken family is a common sight in Key West

the middle of Duval Street. They have a large menu and the quality is above average. Nothing fancy, but Jack Flats has a sports bar feel with better food. They are easy to miss and don’t let the small door fool you, it opens into a huge restaurant space.

For breakfast, you must try Blue Heaven. This notorious quirky outdoor restaurant serves some of the best breakfast food in a unique setting in Florida. They have a tropical décor with plenty of birds and chickens roaming the grounds. The menu is large, but they are known for their pies in addition to the early morning offerings.

Hogfish Bar Grill Stock Island

One of our favorite casual restaurants is Hogfish Bar & Grill on Stock Island.

Blue Heaven is located over on the west side of the Key West, a couple blocks from The Hemingway House on Petronia Street.

By the way, if you don’t like chickens, you won’t like Key West – they are everywhere. Walking either way on Whitehead Street you will find a lot of hens and their chicks roaming the streets year-round.

Hogfish Bar & Grill One of the Best Casual Restaurants

Hogfish Sandwich at Hogfish Bar and Grill

Hogfish Sandwich at Hogfish Bar and Grill is famous.

The fame of the Hogfish Bar & Grill over on Stock Island comes mostly for their exceptional food. It is possible our first taste of hogfish came from this bar twenty-plus years ago. Now their Hogfish Sandwich has such fame, people stop at the Hogfish as they drive into Key West from points unknown.

However, don’t be fooled – this is a BAR with a reputation for food. Finding the Hogfish Bar & Grill can

Sarabeths Key West

Another well-known breakfast and lunch place in Key West is Sarabeth’s.

be a little tricky – use a good GPS and look for Front Street along the waterfront on Stock Island across the small bridge as you leave Key West. It’s worth the stop and even more fun if you stroll the docks with a beer in hand.

Some of the craftsmen near Hogfish have their shops open. They do everything from marine woodwork to art objects from junk! You may even see a manatee or two along your walk. We can also recommend Roostica. This wood fired pizza restaurant is located on the way to Hogfish Grill. The owner of Hogfish started this pizza restaurant in 2016.

Things to do Key West

Good food in Key West can be found by asking your servers, bartenders and hotel staff.

Pepe's Key West

Just good food at Pepe’s – no matter how it looks outside!

In OLD Town, an area of town with classic homes from the days of shotgun homes, cottages and conch homes built in the early 1900s, you must give Sarabeth’s a try. This quaint little place is located in a colorful remodeled home on Simonton Street. Sarabeths started making marmalades from an old family recipe and eventually turned that into a healthy restaurant business.

Known for Key West classic dishes with plenty of fruits and pastries, Sarabeth’s breakfast is excellent. We haven’t tried lunch, since long lines kept us from joining the waiting crowd.

Smallest Bar in the world they say. 124 Duval Street.

The smallest bar in the world is at 124 Duval Street – about the size of a jail cell!

For the first dozen visits to Key West we avoided a place called Pepe’s. It was in a ramshackle-looking building on Caroline Street that we passed when leaving the docks from the Key West Express. I wasn’t looking for Cuban food was my thought.

As with everything else in Key West, nothing is what it seems to be. There is nothing Cuban or Spanish about Pepe’s menu. This is a popular local’s hangout. I think they refuse to paint and fix up the exterior to keep the tourists out! Breakfast, lunch or dinner – never had a bad experience at Pepe’s.

Over on the edge of Bahama Village, near Truman Annex in the upper Duval corridor on a little street called Petronia is a small restaurant called Santiago’s Bodega. This is the place for dinner even if it is hard to find! The décor may be old stuff gone vogue as a style. No matter, the food is really good.

Santiago’s call itself a ‘Tapas” restaurant, but most of these small plates are dinner, not small plates. Try the croquettas, beef tenderloin, pinchos moriunos or the brussels sprouts – all excellent. This is another place where you generally need a reservation, and it is worth it.

BOs Fish Wagon Key West

BOs Fish Wagon Key West looks like a pile of junk – don’t be fooled. Locals love their fresh fish.

We said we were shooting for three days of adventures and things to do in Key West and we have given you enough restaurant suggestions, except for one. Along Greene Street about a block south of the Schooner Wharf, is a rustic ramshackle building called BO’s Fish Wagon. Yes, it was a wagon at one time, but now it looks like a hurricane dropped some scrap material in a heap! Go ahead and click on the link to BO’s Fish Wagon. We can’t describe the dog friendly BO”s, but they have a great fresh grouper sandwich!

We have presented enough restaurant suggestions to last at least for several days or trips! Many of the classic places mentioned in the Bar section also have decent food.  Places like Hogs Breath Saloon, Sloppy Joe’s, Margaritaville and others are acceptable, but the ones above we think are extraordinary!

Attractions and Things To Do in Key West

Hemingway House Key West

The Hemingway House is on the top of most people’s list of things to do in Key West.

In Key West there are attractions and then there are oddities that are just as entertaining and interesting as the ones plastered all over the travel brochures. We will start with the ones every tourist usually sees and then move on to some of the less publicized attractions.

Almost every new visitor goes to Hemingway House. Located on Whitehead Street, the Hemingway House was purchased by Ernest Hemingway in 1931. He resided there with wife number two, Pauline, for several years. Many of Hemingway’s short stories and novels were written in the house. The home has many original artifacts. In addition, about 40 or 50 six-toed cats reside on the property. All are descendants of Hemingway’s cats. Worth a one-time visit as a Key West must see attraction.

If you go to the north end of Whitehead Street, you will find The Key West Aquarium. Keep this one for a rainy day or when the heat gets unbearable.

Museum of History Key West

On Front Street, the history museum is a definite stop for history buffs.

Just a block away is the Key West Museum of Art and History. This museum is run by the Key West Art and Historical Society. They also run the Lighthouse and a couple of other attractions listed here. Many are worth a little time if they interest you. Personally I prefer the Museum during an afternoon rain shower. The history of Key West and the people who settled the area reads like a novel.

Beach at Ft. Zachary Taylor

Snapshot at the small beach at Fort Zachary Taylor.

The Mel Fisher Maritime Museum is worth the visit if you want to learn about his discovery of the Spanish ship Atocha that wrecked in 1622. Fisher recovered an estimated 450 million dollars worth of gold and silver. The museum is on Greene Street visible from the Art and History Museum.

Fort Zachary Taylor is on the southwest side of the island near the Truman Annex, which is a government compound. There is a small beach at the old fort that is good for snorkeling.

Butterfly Conservatory Key West

Plenty of close-up photo opportunities at the Butterfly Conservatory.

The Truman Annex features what people call the Little Whitehouse because President Truman spent so much time in Key West. If you are pressed for time, skip this one.

Bird at Butterfly Conservatory

Not just butterflies at the Conservatory.

Golf Cart Key West

Don’t want to do a lot of walking? Golf carts are a great way to see the island. They are available at many locations.

An attraction you should not skip is the Key West Butterfly and Nature Conservatory. On the south end of Duval street you will see a large yellow building that looks more like a bed and breakfast than a conservatory. Once inside, the rear of the building is covered with a dome that houses thousands of butterflies, birds and tropical plants. The Conservatory has set up a natural setting for the birds and butterflies. Bring your camera! You will have the opportunity to get close-up pictures of the flying inhabitants. This is one of our top three tourist attractions and things to do in Key West.

These and a few other tourist attractions make up the list of the well-known sightseeing places in Key West. Many fall into the category of “must see”, but we have a few others you may never hear about, but are part of the “real” Key West.

Off the Beaten Path Key West Attractions

You will hear about ghost tours and

Key West Cemetery

Ghosts start here!

all the haunted buildings in town. We don’t know about ghosts, but we do think you should visit where the bodies are buried – the cemetery!

The Key West Cemetery was established in 1847 after a previous year’s flooding washed a bunch of bodies out of the old cemetery. They gathered up the bodies and found a 19-acre plot in Old Town to start the new cemetery with immediate customers.

Key West’s cemetery is full of history, with sections for the sailors who died on the battleship Maine in the Cuban harbor sinking in 1898. Another section has victims of the Civil War. Before you go, visit this website to learn about some of the colorful characters buried in this still active cemetery. It’s worth a couple hours and a short walk south on Margaret Street.

Key West Cemetery

Key West Cemetery is a great place for historians.

One attraction that you can visit, or stay overnight in, is the Curry Mansion. This mansion was built in 1869 by one of the first millionaires on the island. William Curry was a wrecker who salvaged wrecks on the reefs around the keys. He built this massive home for his family including a “widow walk”. The Curry is now a bed and breakfast that is popular. We recommend staying in The James House, another restored home, across the street which is owned by the Curry.

The main mansion at Curry offers self-conducted walks through the rooms with period furniture and smallwares. See how wealthy people lived in the 1800s. The Curry Mansion is on Caroline Street just a half block off Duval Street and very convenient to the whole island.

Fort Jefferson Key West

If you have a half day, you must take the trip to Fort Jefferson.

Seaplane Fort Jefferson Key West.

A seaplane is a fun way to get to Fort Jefferson. They pull right up to the beach.

I know we are planning for your three day Key West trip, but here is one attraction that will take half of one day. Take a seaplane to Fort Jefferson and the Dry Tortugas! The Tortugas are a group of islands 70 miles west of Key West. On one of these islands is Fort Jefferson, the largest brick building in the western hemisphere, built in the 1850s.

Fort Jefferson Tour

Taking a tour at Fort Jefferson is the best way to learn about the historical events that took place here. Including the phrase. “Your name is Mudd”.

You know the story of President Lincoln’s assassination. Your sixth-grade history should have mentioned the name Dr. Mudd who treated the assassins. Mudd was imprisoned at Fort Jefferson. He treated all of the prisoners for many years.

Seaplane Adventures will take you to Fort Jefferson for a half day of sightseeing the Fort and snorkeling the island. Boats leave daily from the Key West Bight Marina daily if you want to keep your feet on something solid. Great history and a lot of fun in a seaplane or boating over. This adventure encompasses several activities in a small half-day period including exploring the fort, snorkeling the island and riding in a seaplane!

If you are not up to the half-day trip to the Tortugas and Fort Jefferson, but want a little relaxation, try a sailing charter or one of the snorkeling adventure boats run by Seabago or Fury. Both companies run various types of snorkeling, diving and fun water sports trips out of Key West Bight Marina.

If you want a more personal experience on the water, try the sailing charter Spirit of Independence. You can schedule their regular sunset or fun day trips. Captain Ricky will even offer private charters customized to your liking. Either way, a couple hours on the water can be a relief from the nightlife of Key West.

Key West conch houses

Walking Old Town in Key West is like an architecture review. Many styles influenced by ethnicity of the builder.

Walking Key West – An Adventure In Architecture!

How about a little walk? Between the Cemetery and Hemingway House is

Each era in Key West produced different home styles.

Each era in Key West produced different home styles.

a section of town we have referred to as Old Town. If you spend some time looking at the houses around you, note the 19th-century styles.  Many are conch houses.  Other structures may be shotgun houses and eyebrow houses with some Victorian homes along the way.

Architecture in Key West is a visitor’s guide to the influences of different periods. The exiled Cubans, the Bahamians, the Spanish and of course Europeans who settled in the states and ended up in Key West. Each different influence brought styles from their heritage mixed with the necessities of Key West’s tropical climate. Walking the streets of Old Town Key West is like taking a walking history lesson. Enjoy the sights of the past and newly remodeled structures.

The Must See Mallory Square at Sunset

Finally, every first-time tourist in Key West must visit Mallory Square at sunset. Tourists and locals alike have

Mallory Square Key West

Performers delight visitors at Mallory Square.

made this a ritual for at least 60 years. There is no better place to watch the sun’s majestic entrance into the Gulf.

Mallory Square provides docking for cruise ships.

Mallory Square is empty now, but by sundown it will be packed with people!

The entertainers lining the waterfront will provide a little fun before your evening plans. Some of the acts have been performing at the Square for over 30 years!

As you exit Mallory Square, you may want to stop at El Meson de Pepe for the best mojitos and Cuban food on the island – and try a little salsa dancing!

Your four days and three nights in Key West will be busy if you just do half the things we covered and visit just a few of the bars and restaurants. Maybe you want to relax with a little entertainment.

Entertainment in Key West

It seems the entertainment options are almost all day long. Places like Sloppy Joe’s, Irish Kevin’s and Rick’s seem to start mid-morning and go to the wee hours of the next morning. 

 Here are a few other entertainment options –

  • The Smokin’ Tuna just off Duval seems to bring in a variety of bands starting each afternoon.
  • The Bull on Duval has acts that start in the afternoon and last all night.
  • La Te Da features drag queen shows most evenings.
  • The Hogs Breath Saloon on Duval brings in some really good bands in the evening.
Key West Street vendor

Part of the entertainment in Key West are the street vendors.

Key West also has Coffee Butler Amphitheater that brings in name talent from around the country. Check their schedule when in town.

Street painter Key West

Another street artist. Remember to negotiate prices.

Where to Stay in Key West

There are well over 150 hotels in Key West and another 50 or more bed and breakfast lodgings. Choices range from big chain hotels to local independent owners. Prices are as varied as amenities.

Two bed and breakfast operations we would suggest are The Curry Mansion and The Conch House Heritage Inn. We have stayed many times at The Curry. They offer a breakfast every morning at poolside and happy hour snacks and refreshments every day at 5 PM. Suggestion, try room 302 in the James House, across the street from the main mansion. The primary reason we stay at the Curry Mansion on some occasions is the location a half block from all the action on Duval Street and just a short walk from the docks that moor the Key West Express.

Curry Mansion

Curry Mansion is our favorite Bed & Breakfast in Key West.

The Conch House is in Old Town and is roomy and clean according to friends who have stayed there. Of course, breakfast is offered in the mornings there as well.

There is an abundance of hotels on every part of the island. Every chain has a location somewhere in Key West. You can spend time looking on the travel sites or below are the ones we have stayed in that we recommend. (There are others we have stayed in we won’t be mentioning.)

The Pier House – is another favorite that we have enjoyed manyPier House Boat Races times. Right at the foot of Duval Street. The Chart Room, one of our favorite Bars, is located inside. The Pier House is on the high end from a cost standpoint. The location, clean rooms and waterside bar make it worthwhile. They also have a small private beach and nice pool.

All the way to the other end of Duval Street (south) is the Casa Marina, part of the Waldorf Astoria group of hotels. This gracefully aging beauty was open in 1920 as part of the Henry Flagler group of exclusive hotels he was building along the coast. This old hotel is immaculate, exclusive and right on the Atlantic Ocean with its own private beach. We would highly recommend this facility, but the cost may not be worth it if you plan to spend your days off the property.

Casa Marina Hotel Key West

Casa Marina Hotel Key West is a few blocks off Duval Street. A Henry Flagler original hotel.

The Galleon Resort and Marina is a perfect location if you are planning on taking advantage of the many water sports in Key West. The hotel is on the Gulf side of the Island and has a 90 slip boat marina. They also are a time-share resort, so availability may be limited at certain times of the year. They are priced about the same as the Pier House year round.

The Opal Key Resort says on their website they were ranked as one of the top resorts in the Florida Keys! We are not sure about this lofty ranking, but The Opal has a great location right on the entrance to the Key West Harbor. They also are next to Mallory Square. The shops bordering the marina front are fun with an emphasis on watersports. This is a big hotel and will be priced as the Pier House and others.

Opal Resort Key West

Opal Resort is one of the largest. Just west of Mallory Square.

Right in the middle of Duval Street is the Crown Plaza La Concha Hotel. We haven’t stayed here in several years, but the hotel has been remodeled recently and should be better than our last visit. The La Concha is one of the tallest buildings in Key West and has a great view of the landscape. The hotel has a large wine bar on Duval, and very comfortable lobby. Pricing is just slightly less than waterfront properties.

Bed and breakfast operations dot the landscape and populate almost every street in Key West. Most are reasonable and accommodating.

Warning about booking hotels in Key West. You will find many hotels listed by Sheraton, Marriott, Hampton, Doubletree and other chains. Make sure they match your plans. All of the ones above are far out on Roosevelt Street towards the airport. These locations are about two miles from Duval Street and most attractions. We prefer locations within blocks of Duval, not miles away.

Getting Home….. maybe! Key West Can be Hard to Leave

If you have roamed the island for the last few days, you probably met a lot of people. Servers, bartenders, street vendors, performers, and some colorful characters in the streets. Many of those people were in your position at one time – a visitor. You can be a responsible caring person and choose to go home to tend to life’s routine, obligations and rituals or you can say……To hell with being a responsible person and become a server, bartender, performer or a colorful character in the street…. just like all the people you met!

Boat Races Key West

One of our favorite annual Key West events is the Super Boat Championships in November.

Everyone sees Key West a little differently. Some are attracted to the unrivaled rich history. Others just scratch the surface for a quick get-away. Some people consider a visit to Key West is like taking nature’s Valium!

Many people come for the water sports that abound in the clear blue waters. Some people love the almost 24 hour a day entertainment. Annual events like the Hemingway lookalike contest, Fantasy Fest, Song Writer’s Festival, multiple fishing tournaments, food and wine festivals, Super Boat Championships, and many more bring thousands of visitors. The natural setting of an island between two oceans offers experiences not found anywhere else in the world.

The choice to leave is difficult or in some cases, as we suggested early on, getting home may be a necessity to maintain your sobriety and sanity!

One thing you know is that you will be back. Someday, sitting in your office at home, or at your job at the bank, or when making another appointment, landscaping another house, working at some other diverse occupation, your mind will wander back to Key West and the planning begins once again….

 

Addendum – Getting Back to Key West in a hurry!

Getting to Key West by Boat

For boat owners on the Gulf coast, you can set your GPS to the buoy at the Northwest channel (N24°33’44.2”, W81°49’3.4”) and head down Florida’s west coast. Or from the east coast, you can come around south of the keys and set your GPS to N24°32’42.9”, W81°48’59.2”, which is the entrance to Key West Channel from the Atlantic Ocean.

Key West Express

Key West Express is a fun way to get to Key West from Ft. Myers.

However, if you want to relax and down a couple of cocktails, try the Key West Express. This is a fun way to get to Key West from Ft. Myers or Marco Island. The schedules vary, but they generally leave Ft. Myers around 8 AM and get you to your destination in time to have a dozen fresh oysters for lunch at The Half Shell Raw Bar in Key West. The same estimated schedule applies to Marco departures. The Key West Express boats dock at Key West Bight Marina which is about five blocks from Duval Street and close to every island attraction. As you approach the marina from the channel, you get a feel for the vibe of Key West as the Express passes by Mallory Square, the Sunset Pier at the Ocean Key Resort and the tiny beach at the Pier House.

The fun part about the Key West Express is you can enjoy the ocean spray in the back of the boat, work on your tan on the deck, play cards with friends or just watch a movie. The cost is about $129 round trip, but if you sign up for their emails, there are specials offered at certain times of the year.

Of course, the way thousands of people get to Key West every day is on a cruise ship. One or two ships pull up to the Mallory Square docks daily. They generally are docked by 9 AM, dump thousands of passengers out onto Duval street and to the trinket vendors on Front Street. Then the ships must be loaded and gone before the nightly sunset celebration on Mallory Square. Dumping off thousands of people on the island is good for the many restaurants, shops and retailers on Duval, but not a good way to experience the REAL Key West.

Flying to Key West

We are continually amazed at theKey West Airport number of non-stop flights to Key West International Airport (EYW) from around the country. The last time we checked there were 15 airports that flew straight to Key West, most of which were major hubs.

The airport in Key West is small, but functional (which, not everything in Key West is functional!). They move a lot of passengers through the TSA lines efficiently. When you land there is plenty of taxis waiting to take you anywhere on the island. Some taxis group passengers together and charge a per person set rate by destination zone from five to nine dollars. Fares are regulated, so over-charging is rare. The Key West Airport is a couple of miles from most of the attractions. The airport is located on Roosevelt Avenue on the Atlantic Ocean side of the island and the traffic is rarely congested, which makes access easy.

Flights range from a little over an hour from Tampa, to a little under two hours from Atlanta and around three hours from Chicago. Three hours, in February in 10-degree temperatures up north to a balmy 80 degrees in Key West, is a small price to pay in flight time for a hint of paradise! By the way, there is a small full cocktail bar in the Key West airport baggage claim!

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