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

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.

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.

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!

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.

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.

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

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.

If 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.

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.

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.

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.

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

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.

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.

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.

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.

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 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.

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.

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.

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.

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 19^th 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 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

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!

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 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

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

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.

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

We 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!