Ultimate Key West Itinerary (What to Do, Activities, Attractions & Advice)

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Located 165 miles south of Miami and 90 miles north of Cuba, Key West, Florida is the southernmost city in the continental United States. As such, it’s also one of the most popular places to visit in the county.

There is no shortage of things to do in Key West and the island promises visitors one of the most fascinating sunsets in the country, a laid-back atmosphere, and a unique mixture of cultural influences. Not to mention an explosive nightlife, and a wide variety of water adventures.

It’s no secret that Key West and the greater Florida Keys is one of our favorite destinations in the world and we’re excited to share this quirky place with you.

This guide is extensive and dives deep into all the best Key West attractions, activities, restaurants, offering the ultimate itinerary for anyone that wants to see the best of this awesome island destination.

We’ve spent hours putting this together so that you can go, have fun, and relish in all the best that Key West has to offer.

Don’t leave home without: Lonely Planet Miami & the Keys (Travel Guide)

Key West, Florida Highlight Map

Table of Contents

HOW TO USE THIS MAP: Above you’ll find a map of our highlights in Key West, Florida. Click on the top left of the map to find separate layers marking the route and points of interest. You can hide and show different layers, or click icons on the map to see the names of places we mention in this travel guide. “Star” the map to save it to your own Google Maps, or open the map in a new window for a larger version.


50 Epic Things to do in Key West, Florida


1. Take the Conch Train Tour

Conch Train running on the streets of Key West, Florida

Now that you’ve arrived in Key West, the first you’ll want to do is hop on a Conch Train Tour and get yourself acquainted with the island. This tour operates in a hop on hop off style that takes you to the top spots.

Your ticket, once purchased, is good for the entire day until the last train time as indicated by your conductor. We’d recommend that you get on one of the very first trains and ride the whole loop without getting off.

This will help you get your bearings and give you time to figure out where you want to explore more in-depth on the second pass around.

2. Visit the Hemingway House & Meet the Cats

Cat in a room at the Hemingway House in Key West, Florida
One of many six toed cats at the Hemingway House

Located in the charming Old Town, The Hemingway Home & Museum is a must-see landmark, especially for literature aficionados.

Ernest Hemingway was not born in Key West; the literary icon lived here for a few years and became one of the most famous and well-loved residents of the island.

His former home is now a U.S. National Historic Landmark and it is open to travelers who are eager to learn more about his life and work. You’ll also have the chance to meet several of his famed 6 toed cats, that wander freely around the house and grounds.

Looking to fit the Hemingway Home & Museum into your day of sightseeing? Check out this amazing tour that begins in old Key West where pirates first discovered the island.

You’ll stroll along with the houses of ship captains and wreckers on Whitehead St. learning their history and will pause for a photo at Mile 0.

Then you’ll pass the historic Courthouse, a centuries-old church, and enter Bahama Village and explore a few blocks of this culturally rich African-Caribbean neighborhood.

You’ll wind our way over to the home where Hemingway wrote many of his novels, stroll past the city’s lighthouse, step over to Duval St. to learn about Key West’s Cuban influences and cigar history, and end our tour at the Southernmost Point landmark.

3. Tour Truman’s Little White House

Truman's Little White House in Key West
The Truman grounds are gorgeous!

History lovers have the chance to explore Truman’s Little Whitehouse that was used as the headquarters for the naval station’s command during the Spanish-American War, and two World Wars, as well as President Harry S. Truman’s winter White House.

The charming museum is beautifully preserved and open for guided tours. Though the tours are highly recommended, if you are not interested or you don’t have enough time, you can just visit the small-sized gallery located on the ground floor.

Expect to be transported back to the past through interesting photographs and historical displays. Don’t forget to get a photo of yourself at the presidential podium on your way out!

4. Shipwreck Museum & Lookout Tower

Key West Shipwreck Museum
This museum is amazing, don’t miss it!

One of our favorite museums in Key West is the Shipwreck Museum. The island was home to people that made a living as wreckers, who rescued both bounty and crew from ships that wrecked on the reef off Key West.

Today, many of those artifacts can be viewed in the museum, including some famed treasures. You can even touch a massive silver bar that was recovered from a Spanish galleon.

When you’re done reading pirate lore and admiring treasure, head up to the lookout tour for sweeping panoramic views of the downtown and Mallory Square.

5. Mel Fisher Maritime Museum

Mel Fisher Maritime Museum in Key West, Florida
Entrance to the Mel Fisher Maritime Museum

Mel Fisher is the most widely known treasure hunter in The Florida Keys, so visiting Key West and not stopping at the Mel Fisher Maritime Museum would be a crime!

It is in this museum that you can learn the story of Mel, his projects, his failures, his conquests and his incredible finds in the pursuit of history and treasure.

The museum features artifacts revered from the sunken Spanish galleons Nuestra Senora de Atocha, Santa Margarita and the slave ship Henrietta Marie.  

6. Sunset Celebration at Mallory Square

People watching the sunset from Mallory Square in Key West, Florida
Enjoying another fabulous sunset from Mallory Square

The only place to be in Key West when the sun starts to set is at Mallory Square for the nightly sunset celebration.

Watch the sun going down surrounded by a great number of excited people, local artists and musicians, magicians, jugglers and many other surprises. The festival begins about two hours before sunset and is a must on your Key West itinerary.

Be sure to arrive early to stake out a good spot along the water. If you’re traveling with friends, have one save your spot while the other makes the drink runs! Lines can get long, especially as sunset approaches.

Grab some conch fritters at a food stand, a cocktail, and enjoy one of the largest sunset celebrations to be found.

7. Visit the Mile Marker 0 Sign

Highway Zero Sign in the Florida Keys
Obligatory photo at the Mile Marker 0 sign!

The Mile Marker 0 sign marks the official beginning of Highway 1 north and the Florida Keys Scenic Byway. This road runs the entire length of the Keys, including the Overseas Highway, and up the entire east coast of Florida.

If you’ve road tripped from to Key West, arriving at Mile Marker 0 and taking the obligatory photo is an absolute must.

8. Take A Photo with the Southernmost Point Buoy

Southernmost Point in the USA on Key West
Southernmost Point in the continental USA

Technically the southernmost point of the United States is in Hawaii, but the colorful buoy that marks the southernmost point of the continental United States is right in Key West, so don’t miss snapping a photo.

This is one of the most popular Key West activities and the buoy is one of the most photographed places on the island. Definitely a must-see and, of course, a must-capture moment. But get there early! The line is always long, sometimes queuing for over a mile.

9. Shop & Party on Duval Street

Duval Street Market in Key West
Duval Street Market is great for souvenir shopping

Like every other respectful city, Key West has its own famous road, Duval Street, that is filled with art galleries, outdoor cafes, inviting bars, and large numbers of curious travelers.

The strip stretches from Mallory Square to the Southernmost Point and it offers a great spectacle to travelers from all over the world. Sure, it can be crazy, especially if you choose to explore it by night when everybody is ready to party.

But it is a must-see for those who want to have some fun and completely understand the city. Just keep in mind that this is not one of the places favored by the locals, who seem to be having a love-hate relationship with it.

10. Key West First Legal Rum Distillery

The First Legal Rum Distillery in Key West
The inside is worth making a stop to see

Are you even in the tropics if you aren’t considering at least a tasting of rum? So why not add Key West’s First Legal Rum Distillery to your itinerary!

The location of this distillery at 105 Simonton Street is the original location of Jack’s Saloon from 1900. In 1903, it also became the location of Key West’s Original Coca-Cola bottling company.

It wasn’t until 2012, 90 years after the end of Prohibition, that the distillery would open its doors as the first legal rum distillery on the island.

Today they specialize in tours, tastings, and perfecting the art of making mojitos. Even if you’re not a consumer of alcohol, stop in and look around. The building is super cool and they have some historical stuff on display.

11. Key West Butterfly & Nature Conservatory

Entrance to the Key West Butterfly & Nature Conservatory

If you’re looking for a place to just relax and revive after the intensity of Duval Street, then you’ll want to head for the Key West Butterfly & Nature Conservatory.

Here you’ll find an oasis within the historical district that offers a lush botanical garden, several species of butterfly to observe, and the famed flamingos pair of Rhett and Scarlett.

12. Key West Lighthouse

Key West Lighthouse and Keeper's Quarters

In 1823 the U.S Navy established a base in Key West that led to the construction of the Lighthouse & Keeper’s Quarters that exist today.

With the reef filled waters surrounding Key West, this lighthouse was essential if providing safe arrival for the military and commercial ships that arrived at the island.

Constructed in 1848, the lighthouse stands out in history as it’s first keeper was a woman. That fact alone makes a visit to learn the history of this women worth the visit.

The lighthouse was decommissioned in 1969 and today visitors to Key West can climb the 88 steps to the top of the lighthouse for a panoramic view of the historical downtown.

13. Key West Aquarium

Inside of the Key West Aquarium
We love the ambiance in the Key West Aquarium

While it doesn’t look like anything special from the outside, the Key West Aquarium is actually a very cool place to visit. Offering an insightful and up-close look at the aquatic species that call The Florida Keys marine eco-systems home, you won’t be disappointed if you spend a couple of hours here.

We loved the layout and ambience of the displays, which led us to spending way more time than we had planned. All of the tanks are at eye level, so you can really get a good look at the species that are on display.

If you’re looking for a place to escape the heat of the midday sun, don’t even hesitate to visit this place on your next visit.

14. Book A Key West Ghost Tour

Ghosts and Gravestones Tour in Key West
Ghost Tour parked outside of the Shipwreck Museum

Key West is a place that is so rich in history, pirates, and marine lore that the tales of hauntings and ghosts are virtually endless. If you like to hunt ghosts and hear scary tales, then we recommend you book yourself onto a Ghosts and Gravestones Tour.

This 2-hour tour takes you to some of the most haunted places in Key West, complete with all of the tales to go with the stops. The tour is fully narrated and interactive.

You’ll learn about Robert the Doll, the African Slave Cemetery, various haunted establishments in the city, and then end with a night visit to the Shipwreck Museum.

15. Do A Key West Pub Crawl

Pub crawl stop at the Whistle Bar in Key West

Key West is famous for its party scene and one of the best ways to experience it is by booking a pub crawl. These tours will take you on a narrated tour of the most famous bars and pubs in Key West.

You’ll get to enjoy drinks, hear stories, learn some history, and make some new friends, all while tearing it up on Duval Street.

16. Rent the Floating Tiki Bar with Friends

Aerial view of the floating Tiki Bar in Key West, Florida
That could be you cruising in that floating Tiki Bar!

If a pub crawl isn’t your thing and you just want to party with your friends, then why not rent out a Floating Tiki Bar!

Offering a fully stocked bar, you’ll get to cruise the waters around Key West with your own personal bartender and no strangers.

17. Book A Key West Bike Tour

Bikes parked in the streets of Key West

A great way to get acquainted with Key West and get a little exercise is to join a guided bike tour. Key Lime Bike Tours is a fantastic choice if you’re looking for our specific recommendation.

Ride through the streets of Old Town Key West during a leisurely bicycle tour—a perfect introduction for first-time visitors.

Learn about the island’s history and see highlights such as Mallory Square, Mile Marker Zero, and the Hemingway House. Pedal out to the Southernmost Point Buoy and enjoy panoramic ocean views.

18. Key West Tropical Forest & Botanical Gardens

Orchids at the Key West Tropical Forest & Botanical Gardens
Gorgeous orchids to be seen here!

Established in 1936, The Key West Tropical Forest & Botanical Gardens is the only frost-free, sub-tropical natural conservation habitat and native plant botanical garden in the continental United States.

I don’t know about you, but that intro alone is enough to perk my interest and have me planning a stop. Besides the history and titles, this place is absolute zen and a perfect place to escape the afternoon heat to enjoy some quiet time before sunset down at Mallory Square.


Bucket List Key West Activities


19. Seaplane to Dry Tortugas National Park

Lina Stock sitting on the moat around Fort Jefferson at Dry Tortugas National Park
Feeling small next to America’s largest brick structure

Taking the seaplane to the Dry Tortugas National Park is the ultimate Key West bucket list adventure. Not only will you witness a spectacular view of the Great Florida Barrie Reef from above, but you’ll see the aerial view of Garden Key and Fort Jefferson when you arrive at the park.

Once on the island, you’ll get to tour Fort Jefferson, the largest brick made structure in the United States, learn the history, walk to moat, snorkel, and enjoy secluded beach time. It’s pure paradise and one of the most amazing things to do in Key West.

If you’re not able to book the seaplane, there is also a daily ferry service that runs from Key West. If this is your only option for being able to go, it’s still worth it. Don’t hesitate.

20. Dolphin Watching with Honest Eco

Dolphins swimming off the coast of Key West, Florida
Dolphins seen during our tour with Honest Eco

If you want to go dolphin watching in Key West, we highly recommend you go out with Honest Eco. The trips combine dolphin watching with a snorkeling trip in the Marine Reserve, the perfect combination to get out on the water.

We loved the sustainability of Honest Eco, their eco-friendly boat, knowledgeable guides, and contributions to dolphin research in the waters off of Key West. The trip also included healthy snacks, like veggies, hummus, and fresh fruit during the trip.

In addition, they offered wetsuits that were both clean and in good condition along with good fitting snorkel equipment. You really cannot beat that.

21. Snorkeling on the Great Florida Barrier Reef

Snorkeling trip in Key west
Snorkel trip to the Great Florida Barrier Reef

If you want to catch a glimpse of the Great Florida Barrier Reef, the third-largest barrier reef in the world, you’ll need to book a snorkeling or diving trip out of Key West.

All of the snorkel trips leave from the main harbor and there are numerous companies to choose from depending on the schedule and experience you are looking for.

We’ve actually done this twice, both times with Sebago Watersports, and enjoyed our experience. The catamarans are spacious and stable, making it a pleasant trip to and from the reef in open water.

The water is incredibly clear and the reef is healthy with high numbers of fish to observe. Pack your suit, sunscreen and prepare for an epic day on the high seas.

There are also a number of dive shops on the island that will take you out to the best sites on offer. While we are Advanced Open Water certified Scuba divers, we opted for a snorkel trip and it didn’t disappoint.

22. Parasailing in Key West

Parasailing in Key West
Parasailing in Key West

It’s almost a rite of passage to go parasailing in the Florida Keys during your visit. With stable weather and unreal views, it’s one of the best places in the world to do it. Of course, we couldn’t resist and it was literally the last thing we did before we left.

The operators are professional and good at their jobs, they make you feel comfortable with thorough briefings and even take photos for you.

We’ve been parasailing before but this was hands down the best experience we’ve ever had. We had a gorgeous day and our sail took us high above the water, giving us a great perspective of the area around us.

We saw 3 sea turtles during our fight and even got a good dunk at the end by the boat driver, which makes it memorable. We’d definitely recommend this as you’ll fail to find a more beautiful place to try it.

23. LED Night Kayaking on IBIS Bay

Night kayaking on IBIS Bay in Key West with LED glass bottom kayak
This is a great eco tour to see marine life

If you’re looking for something super unique, then we’d recommend that you take a look at an LED Night Kayaking Tour on IBIS Bay.

The tour departs from the pier in front of the Stoned Crab restaurant next to the Ibis Bay Resort after sunset and spends the better part of 3 hours paddling around the Ibis Bay in search of marine life.

It is an eco-conscious tour, and we found the guide to be both funny and informative. He pointed out a wide variety of marine life and we learned a lot about the eco-system of the waters that surround Key West.

The glass bottom kayaks with light illumination provided an interesting element and allowed us to see everything on the ocean floor as we passed by. If you’re looking for something unique and different, definitely give the night kayaking tour a try.

24. Backcountry Helicopter Tour

Aerial view from helicopter in Key West, Florida
Aerial view from our helicopter tour in Key West, Florida

One of the absolute best things you can do in Key West is to hop in a helicopter and see it from above.

The scenery is nothing short of amazing as you see the layout of the city, island and then venture beyond the shore into the back-country.

This was the highlight of our trip to Key West and you cannot really get a perspective of the area until you’ve seen it from above.

Our extended helicopter tour into the back-country area showed us wild islands, sandbars and massive sharks as we flew around.

Yes, I said sharks. It is really incredible what you can see from above in the crystal clear water below. Do not miss this when you visit Key West!

25. Sunset Sailing Trip

Sunset Sail - Things to Do in Key West
Sailboat with a beautiful Key West sunset in the background

As mentioned before, Key West is famous for its breathtaking sunsets. And since it is such a big thing on the island, there are many ways you can spend this time of the day.

Whether you are on a romantic trip or traveling with friends, joining a Sunset Cruise in Key West is a great option.

Couples can relax and celebrate their love while sipping champagne while the rest of you have the chance to join a lively rum and reggae cruise party.

There’s nothing quite like relaxing on a sunset cruise after a long day soaking up the Florida sun. 

26. Mangrove Kayaking Eco Tour

David Stock kayaking near mangroves in Key West, Florida
David kayaking near the mangroves on an eco tour

One of the reasons to visit Key West is to be on the water, so you shouldn’t hesitate to book an eco-tour that includes kayaking through the mangroves that make up the natural eco-system around parts of the island.

These trips typically take you on calm waters in protected areas to get up close and personal with the mangrove forests. It is here that you’ll experience the quietness and wildlife without the fast pace of the downtown.

The tours are great for all ages and skill levels, feature easy to navigate kayaks, knowledgeable guides and generally last around 2 -3 hours.

27. Charter Fishing Trip with Two Conchs Charters

Lina and David Stock deep sea fishing in the Florida Keys
Celebrating one of our catches while out fishing with Two Conchs Charters

Fishing in the Florida Keys is world-famous. So, if you have the desire to cast a line and reel in some sport fish, you’ll want to book a fishing charter with Two Conchs Charters while in Key West.

Based on Marathon, the fishing capital of the Keys, you’ll be rewarded with spectacular fishing opportunities only a short drive from the downtown.

We booked a half day charter of reef fishing and cannot believe the variety and quantity of fish we were pulling out of the ocean. It was the highlight of our most recent trip to the Florida Keys and highly recommend both the experience and company.


Historical Key West Attractions


28. The Oldest House in South Florida

Oldest House in Key West Museum

One of the most charming aspects of downtown Key West is its historical buildings. This is why you should stop in at The Oldest House in South Florida during your visit.

Built in 1829, the house is located at 322 Duval Street and features portraits, original furnishings, ship models, period pieces, and documents that tell the history of Key West. Guided tours shed some light on the history of the house, the occupants and 1800’s island life in Key West.

The museum is open from 10 am to 4 pm Thursday through Monday, so be sure to plan ahead so you don’t miss it.

29. Audubon House Museum & Tropical Gardens

The Audubon House Museum in Key West

Established in 1960 by Colonel Mitchell Wolfson and his wide, the Audubon House Museum is a beautifully restored three level Captain’s home that was built in the American Classic Revival style of the mid 1800’s.

Today the house offers visitors the opportunity to enjoy the galleries and gardens, all while contemplating the rich history of the house and its presence in Key West.

30. Key West Historic Seaport

Key West Historic Seaport at sunset
Sunset is a great time to stroll the Historic Seaport

No matter your fancy, you’ll find something interesting or fun to do at the Key West Historic Seaport and it just happens to be one of our favorite places to hang out in Key West, too!

Spanning over 20 acres, this seaport features a marina, shops, bars, restaurants, boat tours, and a wooden boardwalk that follows the water. It’s also a great place to spot wildlife, including manatees when the water is warm.

We like to grab drinks here and just watch the daily activities. It also makes for some great people-watching too, if you’re into that. There’s also a really great food tasting and cultural walking tour of the Historic Seaport that is worth doing, too.

31. Fort Zachary Taylor State Park

Cannons within the brick walls of Fort Zachary Taylor in Key West
Huge cannons line the brick halls of Fort Zachary Taylor

Fort Zachary Taylor Historic State Park predated the Civil War and is a National Historic Monument that houses the largest cache of Civil War armament in the world. It is also the southernmost state park in the continental United States.

The park offers history, nature, and spectacular beaches. You could honestly spend an entire day here touring the fort and then enjoying the miles of hiking trails and beaches it has to offer.

The beach area offers public bathrooms, changing stalls, a beach café with food and drinks, chair rentals, and umbrella rentals. There are also plenty of hammock hanging trees available, but you need to bring your own.

Additional Details:

  • Address: 601 Howard England Way, Key West FL 33040
  • Park Hours: 8 am until sundown, 365 days a year
  • Fort Hours: 8 am to 5 pm, daily
  • Cost: $4 per vehicle

32. West Martello Tower Fort

Entrance to the West Martello Tower Fort in Key West
Beautiful brick work and stunning gardens await you at the West Martello Fort

The West Martello Tower Fort is one of three Civil War era structures that exist in Key West. It was built in 1862 and was once used for target practice by the U.S. Navy. Much of the beautiful brickwork and design is still visible today.

While it doesn’t operate as a historic site, it is now home to the Key West Garden Club, who have created a stunning oasis that weaves and integrates beautifully with the brick fort. If you find yourself in Higgs Beach and need a break from the sun, it’s worth a visit.

Additional Details:

  • Address: Located at Higgs Beach by White Street Pier
  • Hours: 9:30 am to 5 pm, daily
  • Cost: Free, donations accepted

33. Africa Refugee Cemetery

World mural at the African Refugee Cemetery at Higgs Beach in Key West

If you’re visiting Higgs Beach, you’ll be hard pressed to miss the Africa Refugee Cemetery and memorial that has been constructed near the parking area. The memorial tells the story of the slave trade in Key West, including the lives of several African slaves that were caught up in the transition period.

The site was added to the National Register of Historical Places in 2012 and is recognized as a nationally significant archeological site.

Take some time to read the displays and look at the map. Contemplate the reality for this people and what they went through. When you’re done, look for the outlines in the concrete. These are the actual resting spots to some of the people that were re

34. Fort East Martello Museum

Entrance to the Fort East Martello Tower Museum in Key West

The Fort East Martello Museum is the last of the Civil War era forts to be found in Key West. Constructed in 1862, like the West Martello Fort, this fort was constructed to provide extra protection of the beach from any confederate sea assaults.

In 1950, the Key West Art & Historical Society opened this site as a museum.

Today you can tour the fort, see its preserved battlements collection of relics from the Civil War, learn about the history of wrecking and cigar making in the Florida Keys, and have your own East Martello Ghost Experience. It’s also the home of the possessed Robert the Doll.

 Additional Information:

  • Address: 3501 S. Roosevelt Boulevard, Key West, Florida, 33040
  • Hours: 10 am to 4 pm Monday to Sunday
  • Cost: $16 Adult

If You’re Looking for Beaches


If you’re in Key West to be a beach bum, then you’re in luck! The island has several fabulous beaches and we encourage you to check out our more detailed Key West beaches guide for more information.

Below you’ll find four that are worth checking out if you’re shorter on time or just want to spend one day soaking up some sun.

35. Smathers Beach

Smathers Beach - things to do in Key West
Smathers Beach is the largest public beach in Key West

If it is an idyllic white sand beach lined up against turquoise waters that you seek on your visit to Key West, then you’ll want to save some time for Smathers Beach. Stretching two miles, this beach offers plenty of free parking, restrooms, lounge chair rentals, and is frequented by food carts throughout the day.

It is the perfect place to truly live the laid-back island life of lounging, unwinding and sunbathing while escaping the hustle of the downtown.

36. Fort Zachary Taylor Beach

Pristine beach at Fort Zachary Taylor State Park in Key West
Fort Zach Beach is our favorite beach in Key West

Located within Fort Zachary Taylor State Park is our favorite beach in Key West. Affectionately known as Fort Zach beach, this stretch of sand is quiet, off the beaten path, and the best place to truly relax into the island life.

You do have to pay admission to enter the park, $4 per vehicle, but you’ll be rewarded with less people, parking, hiking trails, restrooms, a café, and plenty of ocean front beach to enjoy.

37. Higgs Beach

White sand beach at Higgs Beach in Key West
White powder sand can be found at Higgs Beach

Higgs Beach is one of the most popular beaches in Key West due to its accessibility and its stretches of white sand. It is possible to rent loungers here, but people like to visit because it is a fantastic walking beach.

It offers a pier, grassy park, the West Martello Fort, a botanical garden and the African Refugee Cemetery to also enjoy during your visit. You can also find the beach front café, Salute on the Beach here, that offers beachside dining to enjoy.

38. Sunset Key

Aerial view of Sunset Key
Aerial view of Sunset Key

If you seek an exclusive experience, then you’ll want to head for the beaches on Sunset Key.

While not open to the public, it is possible to visit Sunset Key by booking accommodation on the island’s exclusive resort, Sunset Key Cottages, securing a spa appointment, or getting a reservation at the famed Latitudes Restaurant.

Once on the island you can enjoy the amenities on offer including private beach access, pools, and related amenities.


For the Foodie – Best Restaurants in Key West


Key West is a great destination for travelers who love history, art, architecture, as well as spending precious time on the beach.

But it is also a spectacular place for foodies who are always eager to indulge in dishes that make their taste buds go wild.

Whether you want caviar, oysters, ceviche, clams, tuna, or other seafood, you can have them all at this stylish restaurant.

39. Try Key Lime Pie at Kermit’s Key Lime Shoppe

Lina Stock eating Key Lime Pie on a Stick at Kermit's Key Lime Shoppe in Key West
Pass me the Key Lime Pie on a stick!

Key Lime Pie is an institution on the Florida Keys, and no visit to Key West would be official without a visit to Kermit’s Key Lime Shoppe to enjoy their famous chocolate dipped Key Lime Pie on a Stick!

Of course, you can enjoy other takes on the pie here, as well as Key Lime salsa, chutney, taffy, jellybeans, tea, olive oil, and a variety of other takes on the famed citrus fruit. They also offer food, so stopping in for lunch and pie is a totally acceptable way to treat yourself.

40. Brunch at Blue Heaven

Pancakes and eggs Benedict during Sunday brunch at Blue Heaven Key West
Enjoying Sunday brunch at Blue Heaven

The hot seat in town for brunch, on any given day, is at Blue Heaven and it doesn’t come without a long wait. That said, it is worth it. This place not only serves up delicious island takes on eggs benedict and gigantic pancakes, but all done within a laid back bohemian setting.

You’ll get a full belly, bottomless coffee, and full entertainment from the resident chickens. Not to mention that the restaurant offers a garden setting that offers shade and relaxation to complete the whole experience.

Hot Tip: Get there early, as they do not offer reservations and the waits can exceed 2 hours.

41. Eat Stone Crab

Seafood restaurant in the Key West, Florida
Seafood spread at The Stoned Crab in Key West

The Florida Keys is Florida’s top supplier of stone crab claws and not something you want to miss tasting when you are in Key West.

The harvest season starts October 15 and lasts through May 1, and during this time people flock to the restaurants to enjoy the sweet tender meat that is featured on the menu.

The crab is cooked by boiling the claws and then served chilled with a side of traditional stone crab dip that is made up of mustard, mayonnaise, Worcestershire or A1 sauce.

You can find stone crab in pretty much any restaurant that serves seafood in Key West but a couple of our favorite spots to have it for atmosphere are The Stoned Crab and the Eaton Street Seafood Market.

42. Try Conch in the Conch Republic

Key West Conch fritters food cart at Mallory Square
A street food cart offering up fresh Conch Fritters at Mallory Square

Key West once thought to declare itself the Conch Republic, so it’s only suiting that you try conch during your visit. As for how, well that is really up to you.

The most famed way is as conch fritters, where the conch is thinly sliced, deep fried, and served with key lime aioli. It is also enjoyed as conch ceviche in a marinade of onions, peppers, and lime. People also enjoy the conch chowder too.

The best conch fritters in Key West can be had at the Conch Republic Seafood Company. Other good places to try conch are BO’s Fish Wagon, and The Conch Shack.

43. Authentic Cuban at El Meson de Pepe

El Meson de Pepe just after sunset in Key West
Ambiance and Cuban flare await you at El Meson de Pepe

With Key West being located closer to Cuba than it is to Miami, it should be no surprise that the island embraces a Cuban influence.

This ranges from culture to food and it doesn’t get any more authentic than at El Meson de Pepe. (Trust us, we know, we’ve been to Cuba twice!)

Serving up classic Cuban dishes, we’d recommend you settle in for the live Cuban music, order a mojito and soak up the atmosphere before ordering. When you’re ready to order, you cannot go wrong with the Ropa Vieja.

44. Half Shell Raw Bar for Clams & Oysters

Casual dining room at the Half Shell Raw Bar in Key West, Florida

Located on the Historic Seaport, the Half Shell Raw Bar serves up some of the freshest catches in all of Key West and is the best place, in our opinion, to get oysters, and clams.

Offered regular or steamed, the presentation is sure to have your mouth watering when the order arrives at your table.

If raw isn’t your thing, no worries! They also offer a full menu of other seafood delights including stone crab, shrimp, scallops, fresh fish, and conch.

They have a great bar that reminds us of an old maritime establishment and we 100% recommend asking for waterside seating so you can enjoy the seaport while you dine.

45. Matt’s Stock Island Kitchen & Bar for Drinks & Dinner

Tuna taco appetizer at Matt's Stock Island Kitchen & Bar, Florida
The Tuna Tacos at Matt’s Stock Island Kitchen & Bar are delicious!

Located at The Perry Hotel on Stock Island, just north of Key West, is Matt’s Stock Island Kitchen & Bar. If you’re looking for something a little more upscale with a fantastic menu then you’ll want to make a reservation here.

Set on the marina, they offer live music and beautiful ambiance when the sun goes down. We loved the variety of cocktails on the menu, and recommend you order the tuna tacos as an appetizer.

46. Start Your Morning at the Cuban Coffee Queen

Cuban Coffee Queen in Key West

The Cuban Coffee Queen now offers a couple locations in Key West, but we always frequent the location at the Historic Seaport, which is the original location.

It’s also right next to one of the best located public parking lots in the downtown area, so get there early to park and then head straight here.

Operating out of a street shack type building, you’ll get some of the best coffee in Key West here, along with a menu that offers quick takeaway options for both breakfast and lunch.

47. Fisherman’s Café Key West for Lunch or Breakfast

David Stock with the Lazy Way Burger at the Fisherman's Cafe in Key West
David with his Lazy Way Burger at the Fisherman’s Cafe

Our other favorite go to for quick eats is the Fisherman’s Café, also located near the historic Seaport. We always eat here in Key West, sometimes more than once! Operating in a maritime themed street stall, they offer a super fresh menu for breakfast and lunch options.

My go to is always the Shrimp Island Bowl and it never disappoints. We’ve also trued the Cracked Conch Salad, the fish tacos, the Lazy Way Burger (David’s favorite!), and the El Cubano Breakfast sandwich. We’ve never had a bad meal here. Ever.

48. Salute! on the Beach

David Stock having lunch at Salute! in Key West, Florida
Lunch with a beachside view at Salute!

Open for lunch and dinner, Salute! is set directly on Higgs Beach, and during the heat of the day, this place is a shaded oasis with tasty eats and great views. It’s also owned by the same people that offer Blue Heaven.

We stopped in here for lunch on our last visit and ordered the Peel and Eat Shrimp, Fish sandwich special, and the yellow snapper. Everything was tasty and we enjoyed our table that was set in the sand with a nice big umbrella.

49. Latitudes Restaurant for a Sunset Dinner

Latitude Restaurant on Sunset Key in Key West, Florida
Oceanside dining at Latitudes Restaurant – Photo Source: Sunset Key Cottages

Located on Sunset Key, a reservation at Latitudes Restaurant is one of the hottest dining tickets in Key West. They offer award-winning fine dining with stand out offerings like lobster bisque, shrimp carbonara, and a multitude of fresh fish options.

Keep in mind that while breakfast and lunch are casual, they do require country club casual attire for dinner. Be sure to plan well in advance to secure a reservation and if you can, try to get one around sunset time for incredible views over the ocean.

50. Sloppy Joe’s for a Hemingway Mojito

Sloppy Joe's Bar on Duval Street in Key West

Last but certainly not least, is the famed Sloppy Joe’s for food, fun, and tropical drinks. Steeped in history, you’ll also a get a pretty fantastic story and insight into some Key West history when you visit, too. Not to mention, this was one of Hemingway’s favorite hang outs.

To have the true Sloppy Joe’s experience, be sure to order a Hemingway Mojito and The Original Sloppy Joe Sandwich.


Plan Your Key West Vacation


How to Get to Key West

Overseas Highway in the Florida Keys
Driving the Overseas Highway is our favorite way to get to Key West

First of all, getting to Key West is easy. Depending on how long your vacation is going to be, you can choose between driving or flying.

If you have a week, you should go by car. The journey will be an amazing experience, with great landmarks and fascinating landscapes.

But if you plan a shorter vacation, consider flying directly into the Key West airport. In addition, there is also a bus that will take you from Miami to Key West in 4 hours, for about $40.

We’ve now done two epic road trips through the Florida Keys from Miami to Key West stopping off to explore Key Largo, Islamorada, Marathon, and The Lower Keys along the way. It is hands down one of the best road trips in the USA and one of our favorites to date.

If you have time, we recommend you do it too. If you’re looking for our best advice, be sure to check out our Florida Keys Road Trip Guide that highlights all the best stops from Miami to Key West.

Need to book a car for your road trip adventure? We use Discover Car Hire for comparing car prices to find the best deal. They search both local & international rental companies.

How to Get Around in Key West

Lina and David Stock in Key West, Florida
We love to explore Key West by foot!

Once you arrive in Key West, you’ll need to figure out the best way for you to get around. This will likely be a combination of many things due to logistics and your interests.

We’ve done it all and want to highlight some of the best options for seeing the best sights.

  • Walking: Exploring Key West, Florida by foot gives visitors the chance to catch a glimpse of its charming Caribbean architecture and the downtown area is very walkable. Check out this Key West Florida Walking Guide Card to help you navigate around easier.
  • Biking: If you want to explore more than the city, renting a bike is a fantastic idea. There are many hotels and shops that offer bike rentals so you don’t need to bring your own. Not to mention that a bike will save you the stress of finding parking. The island is quite small so if you are ready for a long ride, you can see it in one day.
  • Driving: Parking is not easy to find in the downtown area and is limited to a few strategically placed public lots that are all paid. Street parking is scarce and tickets are frequently issued for illegal parking. We don’t recommend trying to drive around in Key West.
  • Scooters & Golf Carts: We have seen so many scooters and golf carts being used for transportation around Key West, so it’s an option if walking or biking isn’t your thing.
  • Tours: Lastly, we really think the Conch Train Tour or the Key West Trolley Tour are really great options to combine transportation and sightseeing.

Location is Everything: Key West Hotels

The Marker Hotel
Entrance to The Marker Resort

For accommodation, this charming island offers visitors a variety of choices. For people who want to keep things economical, finding a comfortable B&B is the best option.

Angelina Guesthouse is a cozy place where travelers can relax and rest before and after exploring the surroundings. In addition, they serve a delicious breakfast and the prices are very affordable.

For visitors who don’t mind paying extra for their comfort, Key West has many luxurious surprises and Sunset Key Cottages is just one of them.

The Marker (shown above, where we stayed on our first visit to Key West) is located just a few steps from the city’s historic seaport and three blocks from the lively Duval Street.

Lastly, staying outside of the downtown area on nearby Stock Island is also a great option. On our last visit, we stayed at The Perry Hotel and really liked the quiet resort atmosphere versus staying downtown.

Our visit to Key West was made possible in partnership with The Florida Keys & Key West. All opinions, recommendations, and insane love for this quirky island are 100% mine, as always.

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TRAVEL PLANNING RESOURCES

Looking to get started on your trip planning process? Let us help!


Travel Gear & Packing: Check out our packing lists and travel gear guide to ensure you're bringing the right items on your trip.

Book Your Flight: Ready to fly? Check out our tips for finding cheap flights.

Find A Car Rental:We use Discover Cars to compare car prices, find deals and book rentals.

Book Your Hotel: Compare prices and book with our custom-built hotel search engine. You should also check out our tips for finding cheap accommodation.

Find Vacation Rentals: Search vacation rentals & apartments on VRBO for the best prices and options.

Protect Your Trip:Don’t forget your travel insurance! Protect your investment and yourself. Read Is Travel Insurance Worth It?

If you need more help planning your trip, be sure to check out our Step by Step Trip Planning Guide where we break down our process for getting the trip planning process right every single time.


About Lina Stock

Lina is an award-winning photographer and writer that has been exploring the world since 2001. She has traveled to 100 countries on all 7 continents. Member: SATW, NATJA, ATTA, ITWA



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2 thoughts on “Ultimate Key West Itinerary (What to Do, Activities, Attractions & Advice)”

  1. I loved reading about your experience in visiting Key West. Your descriptions really made it come alive for me. Happy travels!

    Reply
  2. *I wish you had mentioned that when visiting the reef, all swimmers should use only eco-friendly sunscreen to help diminish damage to the coral. Or better yet, don’t use sunscreen and invest in a rash guard.
    *My husband and I love the turtle races at Turtle Kraals. Free tickets numbered 1,2,3 or 4 are given at the bar before the races. They race 4 box turtles that live the good life at the Key West Aquarium. This is hilarious listening to the talented announcer call this race as if it were a horse race, when actually these turtles are barely moving. Everyone with a winning number picks one key from approximately 100 and tries the lock for a chance of winning the accumulated money prize. Check with the restaurant for turtle racing nights as it changes by season.
    *While strolling Old Town streets, notice the many “Gingerbread” designs which is the intricately carved wood that adorns these old homes.
    *Notice the huge tropical plants as they never have a freeze that far south.

    Reply

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