Best Things to Do in the Florida Keys | Key Largo to Key West
Last Updated on June 2, 2023
The Florida Keys is a chain of 1700 small islands stretching from Miami to Key West. And there are even more reasons to visit here than there are keys! Find out the must-see sights, fresh seafood, beautiful beaches, and adventurous activities that make this quirky Florida paradise such a charmer.
The history of the Florida Keys is full of pirates, shipwrecks, and at least one rum-soaked writer. (It’s also a classic American road trip – be sure to check out my complete Miami to Key West drive guide!) Time seems to pass differently here as the road stretches over the turquoise ocean and the mainland drops out of sight.
Whether you’ll be spending time in Key Largo, Marathon, Key West or all of the above, I’ve got details on the best things to do in the Florida keys to help you plan your vacation itinerary. I’ll also include recommendations for top tours with great reviews and tips on where to stay.
I independently evaluate all of my recommendations. I might receive compensation for any links you click on my site. Learn more.
In this Guide to the Best Things to do in the Florida Keys
Must-See Sights | Must-Try Foods | Things to Do in the Upper Keys | Middle Keys & Marathon Sights | Lower Keys Sights | Things to Do in Key West | Unique Key West Tours | Where to Stay | Florida Keys Frequently Asked Questions
Must-See Sights in the Florida Keys
Further in this guide you’ll find full descriptions of each of these attractions, but I wouldn’t doing my job if I didn’t ensure these top Florida Keys sights are on your itinerary:
- John Pennekamp Coral Reef State Park: located on Key Largo, this is the first underwater state park in the U.S. Take a glass-bottom boat tour or swim, snorkel, kayak and dive to explore here.
- Bahia Honda State Park: this island in the Lower Keys is known for its beautiful sandy beaches and clear blue waters. Bahia Honda is a perfect day trip for snorkeling, kayaking, beach time and hiking.
- Dry Tortugas National Park: this is one of the most remote national parks, located on an island 70 miles from Key West. Be sure to book tickets well in advance if you want to go.
- Duval Street: the main drag through downtown Key West is home to classic dive bars and icons like the Green Parrot and Sloppy Joe’s bar. You’ll also find restaurants, shopping, and night life.
- Hemingway Home & Museum: the former home of Nobel Prize-winning writer Ernest Hemingway is now a museum famous for its resident cats.
- Key West Sunset Sailing: Key West is a special place for sunset as the southernmost point in the U.S. Make it extra-memorable with a sunset sailing tour or floating tiki bar cruise.
Must-Try Foods in the Florida Keys
- Key lime pie: this sweet treat is found throughout Florida and the Keys. In the Upper Keys, the pie found at Key Largo Conch House and Mrs. Mac’s Kitchen are famous. Porky’s Bayside Restaurant in marathon has a deep-fried version! At the other end of the Keys, Kermit’s Key West Key Lime Shop is a local institution, and Blue Heaven has the most Instagrammable version with a towering fluffy meringue topping. The Key Lime Festival is an annual summer tradition in Key West. And keep an eye out for key lime martinis at bars throughout the Keys.
- Conch fritters: Key West is known as the Conch Republic, so conch fritters, chowder, and other recipes are on many local menus. Conch must be tenderized before eating, and then it tastes slightly sweet, like a clam. A note: overfishing now means that conch is sourced from other locations in the Caribbean. Try it at Alabama Jack’s, Key Largo Conch House, or Mrs. Mac’s Kitchen.
- Hogfish hoagie: Hogfish is a tropical wrasse fish with a hog-like snout found in the coral reefs off the Keys. It’s known for its mild, delicate taste. Try it at the Hogfish Bar & Grill on Stock Island near Key West or at Mrs. Mac’s on Key Largo.
- Stone crab claws: described as having a flavor somewhere between a crab and a lobster, this Keys delicacy is available from October to May. Try it at Keys Fisheries in Marathon or The Stoned Crab in Key West.
- Cafe con leche: this Florida Keys staple is made from strong, sweet Cuban espresso and steamed milk. There are many local faves, but Cuban Coffee Queen, Key West Cuban Coffee, Sandy’s, and Five Brothers Grocery are top coffee spots in Key West. Tip: if you prefer less milk, ask for a “cortadito” (less milk, just as much espresso) or a “cafecito” (no milk).
Best Things to Do in the Upper Florida Keys: Key Largo to Islamorada
Key Largo was once known as Rock Harbor, but was renamed to capitalize on the success of the 1948 Humphrey Bogart film set here. Key Largo is the largest of the Florida Keys and has many hotels, restaurants, and things to do like exploring the nation’s first underwater state park, John Pennekamp Coral Reef State Park.
Halfway between Key Largo and Key West is Islamorada, considered the sportfishing capital of the world. It has the best restaurants, hotels, and atmosphere in the Upper Keys, and is popular for mainlanders seeking a quick tropical excursion.
Explore John Pennekamp Coral Reef State Park & Florida Keys National Marine Sanctuary
John Pennekamp Coral Reef State Park is a must-see as the first underwater state park in the U.S. It includes 70 nautical square miles of the Atlantic. The famous “Christ of the Abyss” statue is here, an 8 foot tall sculpture sunk 25 feet deep. You can also snorkel from the shore at John Pennekamp, canoe or kayak, or take a glass-bottom boat tour.
The adjacent Florida Keys National Marine Sanctuary extends 2,800 square nautical miles from Key Biscayne in the north down to Dry Tortugas. The Florida Reef, the only living coral barrier reef in the continental US, is located just off the Florida Keys. Experienced divers can take an excursion to the artificial reef of the sunken USS Spiegel Grove.
Hours: 8AM to sunset, daily | Cost: $8 per vehicle, plus 50 cents per person
Address: 102601 Overseas Hwy, Key Largo, FL 33037 | John Pennekamp State Park website | Google Maps
Recommended John Pennekamp & Marine Sanctuary tours: John Pennekamp Snorkeling | Half Day Snorkeling | Private Snorkeling Tour | Half-Day Scuba Tour
Discover Dagny Johnson Key Largo Hammock Botanical State Park
This state park is home to 84 protected species of plants and animals, including the American crocodile. Visitors can explore the park’s trails for a chance to see these rare plant and animal species. Most of the more than six miles of trails are paved, making them accessible for bicycles and wheelchairs.
Signs along the trails allow for self-guided nature tours and offer insight into the native ecosystem and wildlife. Ranger-led tours are also available. This is a great addition to your itinerary for bird watching and nature photography.
Hours: Sunrise to sunset, daily | Cost: $2.50 per person
Address: County Road 905, Mile Marker 106 Key Largo FL 33037 | Dagny Johnson State Park website | Google Maps
Grab Lunch and a Cold Beer at Alabama Jack’s
This biker/tiki/dive bar (yes, that’s a lot of slashes!) is found in the town of Card Sound. It’s been around since the 1950’s and has become a traditional first stop in the Florida Keys for many road trippers. They have the reputation of the best conch fritters in the Keys, cold beers, and friendly service. On the weekends the house band, Card Sound Machine, has played in the afternoons for over 30 years. Alabama Jack’s closes at sunset, so you’re not carried off by mosquitoes from the nearby swamps.
Address: 58000 Card Sound Rd, Key Largo, FL 33030 | Alabama Jack’s on Facebook | Google Maps
Try Local Favorites Like Key Lime Pie at Mrs. Mac’s Kitchen
This iconic Key Largo favorite has kitschy decor, fresh seafood, and some of the best coconut shrimp and key lime pie in the Keys (try it yourself to see if you agree!) There are two locations on the Overseas Highway – the first is the original, while the second is better for peak times or if you have a large group.
Address: 99336 Overseas Hwy, Key Largo, FL 33037 | Mrs. Mac’s Kitchen website | Google Maps
Experience Old Key Largo at the Caribbean Club
Opened in 1938, the Caribbean Club is the oldest bar in the Upper Keys. In 1947, Warner Brothers used the hotel and bar as inspiration when writing the screenplay for the Humphrey Bogart and Lauren Bacall film, Key Largo. It also served as a filming location for exterior shots in the film.
Today, it’s a bar and sunset spot for both locals and tourists alike. Thursdays through Sundays, there’s live music on their waterfront stage overlooking the Florida Bay. If you go, be sure to order their trademark Key Lime Rum Punch! (And bring cash since it’s a cash-only bar, or hit up the ATM onsite.)
Address: 104080 Overseas Hwy, Key Largo, FL 33037 | Caribbean Club website | Google Maps
Support the Florida Keys Wild Bird Rehabilitation Center
The Laura Quinn Wild Bird Sanctuary in Tavernier is a center for wildlife rehabilitation, and is home to over one hundred resident birds who cannot be returned to the wild. See rescued hawks, owls, vultures, pelicans, gulls, songbirds, and more. Visitors can learn about the birds and the ecosystems of the Florida Keys. This is a quick stop – less than an hour – interesting for nature and wildlife lovers. Admission is free, but donations are welcome.
Address: 92080 Overseas Hwy, Tavernier, FL 33070 | Website | Google Maps
Discover the History of Diving Museum
For divers and adventurers, the History of Diving Museum is a cool stop and well-done museum. Explore more than 4,000 years of diving history (yes, really) from breath-holding divers to early diving machines and helmets to the revolutionary invention of SCUBA. Includes the world’s largest collection of diving memorabilia.
Address: 82990 Overseas Highway, Islamorada, FL 33036 | Admission: $15; kids 6-11 $7 | Hours: 10AM – 5PM daily | Website | Google Maps
Visit the Florida Keys Discovery Center
Learn about Florida’s history at the Florida Keys Discovery Center, located at the Islander Resort. Permanent exhibits here include First People/Indians, Pirates and Salvagers, Spanish Treasure Fleets, Legends of the Line, and a permanent model replica of Indian Key circa 1840. (Indian Key was the site of a community that salvaged shipwrecks, but today it’s a ghost town; you can tour it by renting kayaks from the outfitter by Robbie’s Marina.)
Their “Stories of the Upper Keys” exhibit delves into Henry Flagler’s Over-Sea Railway, the Overseas Highway, and the 1935 Labor Day Hurricane.
Address: 82100 Overseas Highway, Islamorada, FL 33036 | Admission: $16 | Hours: Wed – Sun 10AM – 5PM | Website | Google Maps
Explore Boca Chita Key in Biscayne Bay
Located within Biscayne National Park, Boca Chita is accessible via boat tours through the park. Its notable for a beautiful lighthouse and a calm protected beach. There are no services here, so be sure to bring a picnic lunch, and pack out everything that you bring in for your return trip. Overnight camping is available; there are restrooms but no shower facilities.
Book Boca Chita cruise | Google Maps
Kick Back for a Meal and a Beer at Robbie’s Marina
Robbie’s is a fun waterfront restaurant and bar with a bonus: from its dock, you can buy a bucket of fish to feed tarpon which grow up to 8 feet. The trick is avoiding aggressive pelicans and trying not to scream when the tarpons jump to snatch the fish! Robbie’s Marina is also a spot for booking local fishing charters and other excursions. You can rent kayaks from the outfitter here to explore Indian Key.
Address: 77522 Overseas Highway, Islamorada, FL 33036 | Website | Google Maps
Try a Classic Cocktail at Holiday Isle Tiki Bar at the Postcard Inn
Calling tiki bar lovers and cocktail connoisseurs! You’ll want to make a stop at the Tiki Bar at the Postcard Inn to see where the Rum Runner was invented. Legend has it that in 1972, the bartender Tiki John was tasked with creating a cocktail to get rid of excess inventory. He mixed banana liqueur, Meyers rum, brandy and grenadine and the Rum Runner was born.
Address: 84001 Overseas Highway, Islamorada, FL 33036 | Website | Google Maps
Chill at the Florida Keys Brewing Company
This beer garden, microbrewery, and taproom is the first of its kind in the Upper Keys. Take a tour of the brewery, enjoy a flight of beers, or just relax and listen to music in their pretty garden courtyard. A must for thirsty travelers and beer lovers!
Address: 81611 Old Hwy, Islamorada, FL 33036 | Website | Google Maps
Sleep with the Fishes at Jules Undersea Lodge
Located at Key Largo Undersea Park, Jules Undersea Lodge is the only underwater hotel in the United States. To get to the hotel rooms here, visitors must scuba dive! Tours are available as well as overnight stays.
Address: 51 Shoreland Dr, Key Largo, FL 33037 | Jules Undersea Lodge website | Google Maps
A note on dolphin experiences: I can’t in good conscience recommend captive dolphin attractions or encounters like the Theater of the Sea or the Dolphin Research Center. Instead I recommend trying to see bottlenose dolphins in the wild with tours like this top-rated Key Largo Eco Tour.
Upper Keys Shopping & Souvenirs
Rain Barrel Village
This quirky spot is a garden oasis with shops, galleries, and boutiques. Spend a few hours and grab a snack at the local eateries too. You’ll want to get a photo with its iconic giant lobster named Betsy! This is a fun itinerary addition, great for souvenirs and Instagram ops.
Address: 86700 Overseas Hwy, Islamorada, FL 33036 | Website | Google Maps
Shell World
Totally kitschy and over the top, this is an iconic Florida Keys tourist stop and great place for shell souvenirs.
Address: 97600 Overseas Hwy., Key Largo, FL 33037 | Website | Google Maps
World Wide Sportsman Islamorada – Bass Pro Shops
This Bass Pro Shops location has all the outdoor gear you need, as well as a full-service marina. The centerpiece of the store is the sister ship to Hemingway’s boat Pilar (which is on display in Havana – the one is here is the boat he reportedly toured and then decided to buy his own). Stop for happy hour at the Zane Grey Lounge tucked into a corner on the second floor to toast the American author and see memorabilia from his time in the Keys. Book a fishing charter, or grab a fresh seafood meal at the Islamorada Fish Company.
Address: 81576 Overseas Hwy, Islamorada, FL 33036 | Website | Google Maps
Best Things to Do In the Middle Keys & Marathon
Marathon is a mini archipelago of its own. Marathon is actually made up of East and West Sister’s Island, as well as a collection of smaller keys, like Boot, Knights, Hog, Vaca, Stirrup, Crawl, Little Crawl, Deer, Fat Deer, Long Pine and Grassy Key.
One of the busiest and most family-friendly parts of the Florida Keys, Marathon offers everything from golf, scuba diving, and snorkeling, to boating, kayaking, and more. Marathon is a good “home base” for adventures in the Upper and Middle Keys.
Swim and Relax at Sombrero Beach
Sombrero Beach in Marathon is a calm public beach perfect for swimming. There are restroom facilities here as well as picnic shelters with grills, and plenty of room to spread out on its long white sand beach. From April through October, loggerhead turtles nest here, so you might see some small areas roped off to protect the eggs.
This is one of my favorite spots in the Keys. I think it’s one of the most beautiful sandy beaches here – don’t miss it! Sombrero Beach is a great option for a beach day if you stay at a hotel that isn’t beachfront – bring a cooler and pick out a spot to relax.
Address: Sombrero Beach Rd, Marathon, FL 33050 | Website | Google Maps
Support Turtle Conservation at The Turtle Hospital
This small non-profit organization is dedicated to the rescue, rehabilitation, and release of endangered sea turtles. Visit on a guided tour to get a behind-the-scenes look at their hospital facilities and see their turtle rehabilitation tanks close-up! The entrance fee and gift shop support their rescue efforts.
The Turtle Hospital is very popular, so be sure to make a reservation. This is a Florida Keys must-see. It’s a great family activity and unforgettable experience!
Address: 2396 Overseas Hwy, Marathon, FL 33050 | Website | Google Maps
Travel Over Iconic Seven Mile Bridge
The Seven Mile Bridge begins around mile marker 47 and connects Knight’s Key in the Middle Keys to Little Duck Key in the Lower Keys. This is the most iconic portion of the Overseas Highway, and frequently gets featured in movies about the keys. (This is a must-see if you’re on a road trip, obviously, as there’s no other road to Key West!)
Explore Bahia Honda State Park
Bahia Honda State Park is one of the islands of the Florida Keys, and is home to a namesake state park. Activities here include visiting its two beaches, snorkeling, kayaking, hiking, biking, and spotting birds and wildlife. The park also has beautiful beaches for swimming. Limited campsites are available and sun umbrellas, kayaks, and snorkeling gear are available for rent.
The hiking trail on the southwest end of the island leads to the top of the Old Bahia Honda Bridge, and has spectacular views of the island and the waters below. This is a Florida Keys must-see! Bring a picnic lunch or grab a snack at the concessions here and enjoy several hours in this peaceful spot. Camping is available in tents, RVs, and cabins.
You can also stop in the concession/gift shop for information on snorkeling tours to Looe Key or contact them via phone to reserve a spot.
Hours: 8AM – sunset daily | Cost: $8 per vehicle | Book a camping or cabin stay | Bahia Honda website | Google Maps
Address: Bahia Honda State Park, 36850 Overseas Hwy, Big Pine Key, FL 33043
Discover Curry Hammock State Park
Curry Hammock State Park offers hiking paths, snorkeling, camping facilities, and sandy beaches. Its ecosystem of mangroves, dunes, and seagrass beds provide a habitat for many wild bird species.
Hours: 8AM – sunset daily | Cost: One person, $4.50; two-plus people, $5.50
Address: 56200 Overseas Hwy, Marathon, FL 33050 | Curry Hammock State Park website | Google Maps
Book a Fishing Charter
Because of the eastern flow of the Gulf Stream, the Marathon area draws larger game fish including and white marlin, tuna and sharks. If you have a sport fishing lover in your group, join a charter group or book a private charter in Marathon.
Recommended fishing tours: Marathon Backcountry Fishing Charter | Marathon Reed Fishing Charter | Ramrod Key Private Fishing Charter
Experience Amazing Diving
The Middle Keys are rich in coral reefs and shipwrecks, and scuba diving is a popular attraction in Marathon. Diving in the Middle Keys off Marathon is a popular attraction. The many historic shipwrecks in the area promise great dive options. Additionally, the artificial reef at Flagler’s Barge has a large variety of tropical and marine life. Check out Better Than Most Watersports, A Deep Blue Dive and Captain Hook’s dive centers.
Lower Florida Keys Things to Do
The Lower Keys are the place for nature experiences at the National Key Deer Refuge and the Looe Key Sanctuary Preservation Area.
Escape to the Private Island of Little Palm Island Resort
One of the best-kept Florida Keys secrets is the hidden oasis of Little Palm Island. One of the most exclusive getaways in the U.S., this four-acre island is home to 30 thatched-roof bungalow rooms dressed in classic tropical chic. All suites have water views, outdoor showers, and private furnished decks. Meals on-island can be taken in the dining room, poolside, beachfront, or in your room. A spa, paddleboards, kayaks, and white sand beaches complete the experience here.
Check rates and see more photos
See Native Species at the National Key Deer Refuge
The endangered Key Deer is the smallest subspecies of the North American white-tailed deer. Poaching and habitat loss had reduced their numbers to only a few dozen animals by the 1950’s, but establishment of the Refuge has allowed for protection and a dramatic recovery. These cuties now number close to a thousand, 75% of which are concentrated on Big Pine and No Name Keys.
Stop at the visitor center for information and drive slowly through Big Pine Key or hike to spot them. The National Key Deer Refuge is an interesting stop for nature lovers and photographers.
Address: 30587 Overseas Hwy, Big Pine Key, FL 33043 | Website | Google Maps
Recommended Nature Experiences in the Lower Keys: Looe Key Private Snorkel Excursion | Private Lower Keys Tour | Mangrove Kayak Tour | 5 Islands Private Sandbar Charter
No Name Pub
This pub on Big Pine Key is famous for having thousands of dollar bills pinned to its walls and ceiling! All are autographed by patrons. Their motto is, “It’s a nice place if you can find it,” and I recommend you do!
But don’t just listen to me: No Name Pub was hailed by Zagat’s as the “best casual dining experience in the Florida Keys.” Feast on their famous pizza, chili, smoked fish dip and sandwiches. Be sure to get a t-shirt or a hat as a souvenir from their shop and ask about its long, storied history… if you can find it! 😉
Address: 30813 Watson Blvd, Big Pine Key, FL 33043 | Website | Google Maps
The Best Things to Do in Key West
Key West is the cultural hostspot of the Florida Keys. You’ll never be short on things to do here, with its history sites, museums, art galleries, restaurants, and nightlife! Don’t miss spending sunset on Mallory Square and save time in your itinerary for a day trip to the Dry Tortugas National Park.
Eat, Drink and Be Merry on Duval Street
Duval Street, and specifically its 6-block stretch within the Key West Historic District, is the epicenter of Key West’s famous party atmosphere. You could spend your entire time in Key West exploring its galleries, shops, boutiques, restaurants and bars.
Be sure to check out Sloppy Joe’s Bar, a hangout of Ernest Hemingway and host to the “Papa Look Alike Contest” in July. Grab some drinks at the Green Parrot Bar that’s been a local institution since the 1800’s – ask for the root beer barrel shot!
Take A Dry Tortugas National Park Day Trip
Almost 70 miles west of Key West lies the remote Dry Tortugas National Park. Accessible only by boat or seaplane, the park is the home of historic Fort Jefferson, crystal clear blue waters, coral and marine life, and a vast assortment of bird life. Dry Tortugas is a bucket-list destination as one of the most remote U.S. National Parks.
Check out my in-depth guide to visiting the Dry Tortugas and book your ferry tickets well in advance.
Ferry terminal address: 100 Grinnell St, Key West, FL 33040 | Website | Google Maps
Have Sunset Drinks at Mallory Square
Mallory Square is a waterfront plaza at the end of Duval Street, adjoining the seaport. With shopping, restaurants, bars, and the best place in Key West to see the sunset, be sure to save time in your itinerary for this spot!
Address: 400 Wall St, Key West, FL 33040 | Website | Google Maps
Chill at Smathers Beach
Located on the south shore of Key West, Smathers Beach is the island’s longest and calmest beach, with nearly a half mile of soft white sand and palm trees. It’s a public beach, with chair rental and food trucks available. Be sure to add it to the list if you haven’t yet had enough beach time and aren’t planning a trip to Dry Tortugas. Note: This Key West beach can have problems with seaweed at times.
Address: 2601 S Roosevelt Blvd, Key West, FL 33040 | Google Maps
Grab a Photo at Southernmost Point
This simple but iconic monument is located at the southernmost tip of the continental U.S., 90 miles north of Cuba. If you don’t have a photo here, have you even been to Key West?
Address: Whitehead St &, South St, Key West, FL 33040 | Google Maps
The Ernest Hemingway Home and Museum
The Hemingway Home was the residence of American writer Ernest Hemingway in the 1930s. Located across from the Key West Lighthouse, it’s the most popular tourist attraction on the island. Legend has it that its many celebrated polydactyl cats are descendants of one that Hemingway owned. The cats have the run of the home and gardens, and you can take a tour with one of their excellent guides to get the inside scoop on all the history here. Including the tale of Hemingway’s “last penny.”
This stop is must-see for history and literature buffs, as well as cat lovers. If you have time, visit the lighthouse across the street for the best views of Key West.
Address: 907 Whitehead St, Key West, FL 33040 | Website | Google Maps
Discover Fascinating History at the Mel Fisher Maritime Museum
Locals laughed at the Midwest chicken farmer-turned treasure hunter Mel Fisher, who moved to Key West with his family in 1969. They searched for 16 years until they hit paydirt: the wreck of the Spanish galleon Nuestra Señora de Atocha, sunk in a hurricane off the Keys in 1622. It was the greatest maritime treasure in history, worth an estimated $450 million. The museum contains exhibits and artifacts showcasing the maritime history of Florida and the Caribbean.
Address: 200 Greene St, Key West, FL 33040 | Website | Google Maps
Key West Butterfly and Nature Conservatory
Take a break from Duval Street and walk among hundreds of butterflies & birds including flamingos in this glass-enclosed conservatory. In the learning center, you can explore butterfly migration and science, then look for butterfly souvenirs in the adjoining gift shop. Be sure to wear bright colors or bring a colorful scarf if you want the butterflies to land on you!
Address: 1316 Duval St, Key West, FL 33040 | Website | Google Maps
Snap a Photo with the Mile Marker 0 Sign
Located in Key West, the Mile Marker Zero is where Highway 1, one of America’s classic highways, ends. Be sure to get a selfie here.
Location: The corner of Fleming Street and Whitehead Street a short distance from Green Parrot | Google Maps
Take in History at the Truman Little White House
Harry S. Truman vacationed here under orders from his doctor that he take a warm vacation. He also had friends, cabinet members, and foreign officials visit for fishing trips and poker games. Truman set up shop there for 175 days of his presidency from 1946 through 1952, which gave the circa-1890 naval site the name “The Little White House.” The surrounding neighborhood, known as Truman Annex, is a leafy shaded area with parks and vacation homes.
Address: 111 Front St, Naval Air Station Key West, FL 33040 | Website | Google Maps
Grab a Drink at the Oldest Bar in Florida, Captain Tony’s Saloon
Originally built in 1851 as an icehouse that doubled as a morgue, Captain Tony’s has a storied past. In recent years it’s been known as the favorite watering hole of such legends as Ernest Hemingway, Truman Capote, Tennessee Williams, Shel Silverstein and Jimmy Buffet. Stop in for a cold beer and ask about the saloon’s namesake, Captain Tony.
Address: 428 Greene St, Naval Air Station Key West, FL 33040 | Website | Google Maps
Unique Key West Tours & Special Interests:
- Key West Food & Culture Walking Tour Eat your way around Key West with this walking tour of local eateries handpicked by a local.
- Literary Walking Tour Stroll around the Old Town to the former homes and favorite haunts of writers that have called the island home, including Shel Silverstein, Tennessee Williams, and Robert Frost.
- Key West Trolley Tour Explore Key West at your own pace with this hop-on, hop-off trolley tour. A local guide shares history, lore, and legends of Key West.
- Key West Bicycle Tour Pedal between highlights of Old Town Key West with narration from an excellent guide.
- Want to hear the haunted history of Key West? Take a Dark Side of Key West Tour. Or visit the Fort East Martello Museum to meet Robert the Doll, who regularly tops lists of the most haunted dolls in the world. You can also roam the Key West Cemetery until sunset – set on a self-guided tour with tips and downloadable map here.
- Get adventurous with a Key West snorkeling cruise, SNUBA tour, or Parasailing Adventure
- Experience the local Key West pub scene on a Key West Pub Crawl or Tiki Cocktail Class
- Finish your trip with an extra-special sunset cruise experience: a Key West Sunset Sailing Tour or Floating Tiki Bar Cruise
Key West Shopping & Souvenirs
Books & Books
This indie bookstore was founded by author and Key West resident Judy Blume and is ground zero for Key West’s literary scene.
Address: 533 Eaton St., Key West, FL, 33040 | Website
Kino Sandals
These comfy, locally-made sandals have classic Key West attire since the 1960’s. Pick up a few pairs to take home as souvenirs.
Address: 107 Fitzpatrick St, Naval Air Station Key West, FL 33040 | Website
Tour A Rum Distillery & Take Home Tasty Libations
Key West is home to two rum distilleries: Key West First Legal Rum Distillery and Papa’s Pilar (named for Ernest Hemingway’s one true love, his boat Pilar).
Rodriguez Cigar Factory
Visit the oldest cigar company in the Florida Keys and bring back a unique souvenir for all the cigar-lovers in your life. Tours include demonstrations, a cigar, and Cuban espresso.
Address: 113 Fitzpatrick St, Key West, FL 33040 | Website
Keez Beez
Honey is one of my favorite souvenirs when I travel. Keep an eye out for Keez Beez honey, made by local bees from island flora, in grocery and souvenir stores. Or have it shipped from their website or Amazon.
Where to Stay in The Florida Keys | Top Accommodation Picks
Check out these top picks of where to stay from Miami to Key West.
Best Key Largo Hotels
$ Gilbert’s Resort | Budget waterfront stay with pool, private beach, tiki bar and views. Check rates on Booking.com | Expedia
$$ Sunset Cove | Rooms and cottages close to sights; pet-friendly rooms, breakfast, kayaks, and private beach. Check rates on Booking.com | Expedia
$$$ Coconut Palm Inn | Resort in Tavernier with rooms and suites, breakfast, and thoughtful service touches. Pool, private beach, kayaks. Check rates on Booking.com | Expedia
$$$$ Kona Kai | Luxury adults-only resort and botanical gardens in Tavernier. Spa, hot tub, heated pool, tennis in a spectacular setting. Check rates on Booking.com
Best Islamorada Hotels
$ Sunset Inn Trendy, family-friendly budget stay with pool, close to sights. Check rates on Booking.com | Expedia
$$ Lime Tree Bay Resort Studios, rooms, and 2-3 bedroom suites, some with kitchenettes. Beachfront with pool and breakfast. Check rates on Booking.com | Expedia *I just stayed here in December and it was such a chilled-out place with friendly staff and other travelers!
$$$ Islander Resort Stylish resort with private beach, 3 pools, lanais, many amenities. Check rates on Booking.com | Expedia
$$$$ Cheeca Lodge Luxury resort with spa, golf course, pools, tennis, private beach. Check rates on Booking.com | Expedia
Best Marathon Hotels
$ Coconut Cay Resort | Colorful budget hotel with a pool, mini-fridge, microwave, kayaks. Check rates on Booking.com | Expedia
$$ Seascape Resort & Marina | Midrange beach resort with kayaks, paddleboards, bicycles, mini-fridges, microwaves | Check rates on Booking.com | Expedia
$$$ Isla Bella | Luxury resort with rooms and 1-2 bedroom suites, some with kitchenettes. Beachfront with pool, spa and restaurants. Check rates on Booking.com | Expedia
$$$ Tranquility Bay Resort | Luxury resort with rooms and 2-3 bedroom cottages. Beachfront with pools, spa and restaurants. Check rates on Booking.com | Expedia
Best Hotels in Key West
$ Blue Marlin Motel | Bright budget stay with a pool in a great location. Parking available for an extra daily fee. Check rates on Booking.com | Expedia
$$ Harborside Motel & Marina | A top midrange Key West pick with pool, kitchenettes, and free parking. Check rates on Booking.com
$$$ Havana Cabana | Resort style hotel with pool, bar, restaurant and fun vibe. Hourly shuttle to Duval and free parking. Check rates on Booking.com | Expedia
$$$$ Southernmost Beach Resort | Luxury resort in historic Old Town with pools, restaurants, spa, and private beach. Parking available for an extra daily fee. Check rates on Expedia
Don’t miss my guide to the best Airbnb rentals in Key West, too!
Frequently Asked Questions About The Florida Keys
How to Get to The Keys
The airports in the region are Fort Lauderdale (FLL), Miami International Airport (MIA), and Key West Internatonal Airport (EYW). From there you can rent a car and drive – don’t miss my Florida Keys Road Trip guide with tons of tips!
Search flights to Miami (MIA) ⫸
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Which is the best Key in Florida?
Key West. If you have limited time in the Keys, head straight to Key West. Here you’ll get to experience the history, fun, and laid back vibes that the Keys are known for, all in one package. Visit the Hemingway Home, experience the nightlife and food of Duval Street, and relax on Smathers Beach.
When is the best time to visit the Florida Keys?
The best time to visit Key West is between March and May. During these months you’ll find less crowds and more reasonable hotel rates. Hotel rates are at their highest during the winter season as well as during special events like Key West Pride in early June.
Be aware that June to November is hurricane season. Hotels are affordable, but the weather is hot and humid and there is a risk of hurricanes.
Where is the best place to stay in the Keys?
If you’re on a road trip and only want to make a few stops, stay a few nights in the Middle Keys around Marathon or Islamorada, and then book a second hotel in Key West. You’ll be able to see all of the Keys’ sights on day trips from those home bases.
How long should you stay in the Keys?
I recommend a week if you plan to fit in many sights of the Keys plus a Dry Tortugas day trip. If you want to spend most of your time in Key West, 4-5 days should be enough.
What’s the best way to see the Florida Keys?
The best way to experience all the sights, eats, and quirky roadside stops of the Florida Keys is on a road trip! Check out my Miami to Key West road trip guide and get a preview below! I took a mini-road trip in December of the Upper and Middle Keys and made a reel of my adventures.
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Ready to pack a bag? Save these best things to do in the Florida Keys for planning!
