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2023 Florida Keys Road Trip to Key West -The Ultimate Florida Road Trip

Keys Map with Key West

Florida Keys Road Trip to Key West – One of the Best Florida Road Trips

Taking a Florida Keys road trip to Key West is not only one of the best Florida road trips, but maybe one of the most famous road trips in the world.

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.

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 the sunset in Key West.

Ways to Get to 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 way to get to Key West 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, and the sports fishing capital of the world, Islamorada, are 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 and things to do in Key West for about three nights.

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 taking a roadtrip to Key West. You don’t have a choice. Route 1 from Miami to Key West is one road!

The fun begins when you enter the islands. From Key Largo to Key West road trip 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 is certainly half the adventure!

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

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

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 to Key Largo.  A collection of bridges will have you crossing more than three dozen other islands before the last island of Key West.

But slow down! We are already going to take you on a detour on your Florida Keys road trip!

About a mile out of Miami-Florida City Rt. 1, you will see a road sign directing you to Card Sound Road veering off to your left and going south. Take it!

Alabama Kacks - Frlorida Keys road trip to Key West
Alabama Jacks Key largo dive bar everyone loves on a Florida Keys road trip.

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 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.

Caribbean Club first stop on Florida Keys road trip to Key West
Caribbean Club was a sie for Bogart and Bacall’s movie named Key Largo.

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 FloridaKeys road 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.

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 mile markers. They will help you find everything along your Florida Keys road trip 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!

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.

Caribbean Club’s 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 Florida Bay. If you don’t recognize the name, Jimmy Johnson is the former coach of the Dallas Cowboys.

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.

Key Largo roadtrip to Florida keys include John Pennekamp State Park
This must-see state park on your Florida Keys road trip to Key West is in Key Largo. Most of it is underwater!

Key Largo and Islamorada Stops on Florida Keys Road Trip

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 injured or entangled by fishing lines or nets. You can see numerous species in the sanctuary rehab center. A kind donation would help preserve the Key’s wildlife.

Oceanview Sports Pub
Oceanview Sports Pub is owned by former Pittsburg Steelers.

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.

This Florida road 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. There are additional interesting stops in the Florida Keys during your Florida Keys road trip.

Theater of the Sea Gives Insight to Wildlife in the Keys

Theater of the Sea Islamorada is part of your ultimate Florida road trip.
Theater of the Sea Islamorada is a place to learn about sea life.

At MM 84.2, you will see a big sign on the south side of the road 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 on your Florida road trip Florida Keys Key West
Amazing what dolphins and other mammals can be taught. Theater of the Sea is a fun stop.

Islamorada is the Sportfishing Capital of the World

If you have been observant, 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. 

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 ocean front hotel are 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.

How many Islands and Bridges are there in the Florida Keys

Bridges along US 1 connect the major islands. There are about 1700 islands in the Florida 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.

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!

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

A resort near the water Description automatically generated
Hawks Cay Resort is a sportfishing and family oriented resort.

Hawks Cay is a place for good old-fashioned family fun. The resort has every possible saltwater activity, with a 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 your Florida road trip 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 can swim with the dolphins (and adults too).

Marathon is Near Half Way on Your Florida Keys Road Trip to Key West

Crane Point in Marathon on your Ultimate Florida Road Trip
Crane Point in Marathon is a place to see how people lived in another century.

One big development just before you get to Marathon, Florida 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 Florida Keys we discuss is at MM 50. Crane Point Museum and Nature Center is one of the coolest places in the Keys 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 at Crane Point 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!

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!

Seven Mile Bridge - Florida Road trip Florida Keys to Key West
One of the most beautiful seven miles of road in the world is the seven mile bridge heading to Key West from Marathon, Florida.

Half Way Through the Florida Keys and Key West Mile Marker 0

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 bridge (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 prosperity lasted 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 are fascinating, but the real story is in the spectacular views on both sides of the bridge.

Florida Bay on your right and the Atlantic Ocean on your left make 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.

Bahia Honda State Park along the ultimate Florida road trip.
Nice beaches, campgrounds and shallow water snorkeling highlight Bahia Honda State Park.

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 wholly 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 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.

Key Deer Big Pine Key are part of the sights on the ultimate Florida road trip.
Key Deer on Big Pine Key are about the size of a large dog. A unique species to Florida.

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 its walls. We 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 things to do during your Florida Keys road trip to Key West….Welcome to Key West - Florida Key road trip to Key West

AND NOW  THE FLORIDA 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 the 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.

Sloppy Joe's Key West
Sloppy Joe’s Key West may be the icon destination and top of the list of things to do in Key West.

We always wonder, what has changed in Key West? 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 in Key West? 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.  

If you fly into Key West International Airport, right beside the baggage retrieval conveyor is a bar! A Rum Runner while waiting for your bags is not all bad – welcome to Key West……  this bar sets the tone for your trip.

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!

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.

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.

Irish Kevins Key West

Is There a Real Irish Kevin?

Yes, there is a real Irish Kevin. We caught him one day when he spontaneously had to fill in one day when another entertainer wasn't avalable.

Irish Kevin's is on of the famous bars in Key West.

Irish Kevins Key West gang

Irish Kevin's is Always Fun

This famous Key West place a door or two from Sloppy Joe's is known for their salty entertainment you can't miss while walking down Duval Street.

Captain Tony's a must see on a Florida Keys road trip to Key West
Captain Tony’s was the original Sloppy Joe’s. See the grouper with the open mouth at the top of the sign? A pastime in Key West is attempting to toss quarters into the grouper’s mouth.

Just west of Sloppy Joe’s on Greene 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 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 included The Green Parrot on Whitehead Street in this list. In fact, they would have been included on our list of the best dive bars in Florida. 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 despite the new public image.

Half Shell is part od Florida Keys road trip to Key West
The Half Shell Raw Bar is the place for some of the freshest oysters and clams in Key West.

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 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.

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!

Where do the locals go in Key West? These are off the grid favorites.

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.

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

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 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 about 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 from 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.

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

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-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.

Chart room on road trip to Key West
This tiny bar, the Chart Room, may have had a lot of important decisions made by city leaders in the past.

We hate to even publicize the next place! It’s very small, already full of locals, regular travelers and city 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 Best Restaurants in Key West with The Best Food in Key West

Key West Pink Shrimp only on a Florida Keys road trip to Key West
Key West Pink Shrimp – Notice the distinctive darker circle on the back third of the shell.

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.

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 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 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.

Blue Heaven 2If you want good basic bar food that covers all the bases, try Jack Flats in 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 are 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.

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.

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.sarabeths key west e1603548219879

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

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 1900’s, 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.

Small Bar is on your Key West road trip
Smallest Bar in the world they say is at 124 Duval Street.

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.

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 calls 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 Road Trip

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. Actually, we 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 closeup 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.

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

Key West cemetery is an attraction on road trip.You will hear about ghost tours and 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 in the middle of Old Town in Key West.

Curry Mansion Bed Breakfast Key West road trip
This late 1800s table and setting is part of the tour of the Curry Mansion.

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 1800’s. 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 days full of Key West road trip attractions, 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 which are Florida Keys and Key West Road Trip
Walking Old Town in Key West is like an architecture review. Many styles are influenced by the ethnicity of the builder.

Walking Key West – An Attraction In Architecture!

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

Each era in Key West produced different home styles.
Each era in Key West produced different home styles.

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 Mallory Square at Sunset is Nightly Attraction

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.

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!Mallory Square provides docking for cruise ships.

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. 

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 breakfast every morning at the 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.

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 – stayed here many

Pier House Boat Races
This was shot at the Pier House during the 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 their 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 property.

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 around.

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.

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.

What is the Best Beach in Key West?

The best beach in Key West is a matter of location and opinion. There are several. The main ones are;

  • Smathers Beach on the south end of the island. Probably the largest and most populated, but it is large enough not to be as crowded as others.
  • Higgs Beach is also on the south end of the island just west of Smathers Beach.
  • Fort Zachary Taylor beach is on the far westerly island near Fort Zackary State Park.

The ones above are the three largest beaches. Your choice may be the one nearest your hotel. There are a few more including some small local’s favorites. More complete beach resource is available at this location.

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!

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

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

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! A Florida Keys road trip to Key West could result in permanent residence!

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 for a Florida Keys road trip 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 the 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 the 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.

Temporary note: Ft. Myers schedule has been cancelled due to hurricane Ian.

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 everyday 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 on to Duval street and to the trinket vendors on Front Street.

Then, cruise 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

Key West AirportWe are continually amazed at the 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 nonstop 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 are 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! As we stated earlier, there is a small full cocktail bar in the Key West airport as you enter – only in the Florida Keys and Key West!

A Florida Keys road trip to Key West travel reminder. You assumedly will be going home. If you miss a few attractions coming down the Overseas Highway, they can be visited on the road trip home!