52 super cool things to do in Key West

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What to do in Key West?

The southernmost key of the Florida Keys — a 120-mile chain of islands off the Sunshine State’s southernmost tip — Key West is unlike anywhere else on Earth. The two-by-four-mile island has cultivated a quirky charm and laid-back vibe, making the so-called “Conch Republic” one cool place to visit.

If you’re thinking about a visit to the Sunshine State’s southern gem, now’s the time to go. June is, on average, one of the most affordable months for Key West airfare compared with the rest of the year. And to get you started, we have 52 super cool things to do in Key West that won’t break the bank. Why not hop on a flight and check them out for yourself? Start your flight search on Cheapflights.com and keep reading for all the cheap and free things to do once you’re there.

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Search for sunken treasure

Treasure hunter Mel Fisher discovered the “Atocha” off Key West and today visitors can dive to the sunken vessel and explore it for themselves. Afterwards, they can check out The Mel Fisher Maritime Museum, which houses Spanish galleons discovered by Mel Fisher and his crew, as well as a number of exhibits.

Do Duval Street

No trip to Key West is complete without a walk down Duval Street. Populated with bustling bars and shops, this is the place to eat, drink and shop.

Eat Key West pink shrimp

Tender Key West pink shrimp are harvested from the coral sands in the clear waters of the Dry Tortugas from November to June. One of the best places to sample the sweet shrimp, which are recognizable by a distinctive red dot on each pink shell, is Schooner Wharf Bar. The restaurant serves a variety of shrimp dishes, like drunken shrimp, which are taken straight off the boat, then boiled in beer and spices and served chilled.

Take selfies at the Southernmost Point buoy

The iconic Southernmost Point Buoy, which marks the southernmost point in the continental U.S., is an iconic spot for a photo-op. Erected in 1983 by the City of Key West, the Southernmost Point Buoy is a mere 90 miles from Cuba.

Explore Hemingway’s Home

Ernest Hemmingway's Key West house
Ernest Hemingway lived in this Spanish colonial villa with his second wife Pauline and their two children from 1931 to 1939. Hemingway wrote many of his best-known works in the second-story writing studio. (Image: Laurence Norah/Florida Keys News Bureau)

Take a tour of the Hemingway Home and Museum, where Nobel and Pulitzer Prize winner Ernest Hemingway wrote many of his famous works. The grounds are still inhabited by descendants of his six-toed cat.

People watch in Mallory Square

Buskers congregate among the tourists and locals who converge on Mallory Square to take pictures, people-watch and celebrate the sunset.

Sip a Rum Runner

The original Rum Runner drink was born out of a challenge: to make a cocktail out of overstock liquor at the Tiki Bar at the Postcard Inn Beach Resort & Marina at Holiday Isle in Islamorada. Plenty of bars in The Keys have added this sundowner to their drink menus, including Pepe’s Café & Steakhouse, the oldest eating house in Key West. The Hog’s Breath Saloon also makes the sunset-colored concoction; a mix of banana liquor, Meyers rum, brandy and grenadine.

Get your passport stamped

The Conch Republicwith the motto “We seceded where others failed,” was born on April 23, 1982, when the Florida Keys staged a ceremonial “secession” from the U.S. after a U.S. Border Patrol checkpoint was set up on the Florida Keys Overseas Highway, the only road in and out of the Florida Keys. The spirit of the Conch Republic is alive and well at the checkpoint, which issues its own passport and novelty stamp.

Go offshore

Hire a chartered boat and head out to the Marquesas, an uninhabited ring of islands 25 miles west of Key West. The idyllic islands provide up-close encounters with sea life and are popular for game fishing.

Eat Key lime pie

a slice of Key lime pie
Key lime pie is the signature dessert of the Florida Keys. (Image: Bob Krist/Florida Keys News Bureau)

The Keys’ signature dessert, Key lime pie, is a must-try. The iconic yellow-hued pie made with limes and condensed milk nestled in a graham cracker crust, is on the menu at many restaurants and bars across The Keys. Try it at Kermit’s Key West Key Lime Shoppe.

Explore one the world’s largest artificial reefs

The USNS Gen. Hoyt S. Vandenberg transport ship wasthe second largest vessel in the world to be purposely sunk to create an artificial reef. Divers can SCUBA to the artificial reef, which takes over-tourism pressure off of other coral reefs and affords SCUBA divers with alternative dive sights to explore.

Hunt for hogfish

With a light, melt-in-your-mouth texture, hogfish is a delicious and popular fish in The Keys – if you can get it. Be on the lookout for the seasonal catch at restaurants across Key West.

Go snorkeling

Snorkel above colorful coral reefs, shipwrecks, seagrass beds and fish at the Florida Keys National Marine Sanctuary, which has the only coral barrier reef in North America and the third-largest coral barrier reef in the world.

Take the train

Conch Tour Train in Key West
All aboard the faux train for a fun time. (Image: Bob Krist/Florida Keys News Bureau)

Take a ride on the Conch Tour Train, a 90-minute ride through Old Town Key West that allows riders to hop on and off at three stops — Station Depot for shopping and food, Truval Village for the Ernest Hemingway Home and Museum and Southernmost Point Buoy and Flagler Station, right behind Mallory Square.

Celebrate Pride

More than 200,000 LGBTQ visitors travel to Key West each year for fun in the sun as well as annual Pride events like Key West Pride in June and Womenfest in September.

Go to the movies

The Key West Film Society runs South Florida’s only nonprofit, independent film multiplex, Tropic Cinema. Open year-round, Tropic Cinema hosts screenings of contemporary, independent and foreign films. The Key West Film Festival is held each fall and celebrates films and filmmakers from around the world.

Take an art stroll

Discover new artists and galleries via monthly art walks like Walk on White, held on White Street from Southard Street to United Street and Truman Avenue on the third Thursday of each month; Upper Duval Street Art Stroll on Caroline Street and Green Street on the first Friday of each month; and Art and Ambiance Walks in the historical Seaport neighborhood on the first Thursday of each month.

Get a bird’s eye view

Key West from the air
This tiny island is packed with fun and adventure. (Image: Andy Newman/Florida Keys News Bureau)

For one of the best views in Key West, climb the 88 steps of the Key West Lighthouse to the observation deck for a bird’s eye view of Key West and the surrounding turquoise waters.

Be a beach bum

Near Duval Street, there is a duo of beaches: Higgs Beach is a popular place to pick up shells and take a dip, while South Beach is a 200-foot-long stretch of sand that’s a peaceful spot to soak up the sunshine.

Get a clear view

Don’t feel like getting wet? Board a glass bottom catamaran to catch glimpses of sea turtles, stingrays and colorful fish. Many chartered boat companies also offer sunset cruises in comfy glass bottom boats.

Get crackin’

Half Shell Raw Bar is a popular place to go for stone crabs, which are harvested offshore and in season from Oct. 15 to May 15.

Celebrate the sunset

Tightrope walker in Key West's Mallory Square
Busker Will Soto walks a tightrope at the sunset celebration in Key West. The sunset celebration at Mallory Square is a daily ritual for visitors to this subtropical island at the bottom of the Florida Keys island chain. (Image: Bob Krist/Florida Keys News Bureau)

It’s tradition in The Keys to watch the sunset from Mallory Square, where locals and visitors gather for unobstructed postcard picture views of crimson and gold sunsets.

Stop by Sloppy Joe’s

Sloppy Joe’s has been a beloved bar ever since it opened its doors on Dec. 5, 1933, the day Prohibition was repealed. After several name changes, Sloppy Joe’s current name was encouraged by Ernest Hemingway, a patron of the saloon. The lively bar hosts live music and an annual Hemingway Look-Alike Contest.

Take a time out

The small West Martello Tower is a peaceful and picturesque historic defensive fort. The tranquil space is one of a handful of free tourist sites in Key West.

Go SNUBA

Traveling with kids in tow? Don’t have a SCUBA dive certificate? Explore colorful coral reefs and sea life via SNUBA, a surface-supplied breathing system which is similar to SCUBA diving but doesn’t require a dive certification and allows children as young as eight years old to participate.

Walk around Bahama Village

Blue Heaven restaurant in Key West
In the 1930s, author Ernest Hemingway officiated boxing matches at Blue Heaven in Key West’s historic Bahama Village. (Image: Andy Newman/Florida Keys News Bureau)

Founded in the early 1800s by Africans migrating from the Bahamas, the neighborhood is home to many cultural sites, including an 1860 African Burial Ground and a Civil War-era fort. It’s also a popular place to eat (don’t miss dining al fresco on Floridian-Caribbean cuisine at Blue Heaven) and shop (score souvenirs at the Bahama Village Market, an outdoor market selling straw hats, seashells and Florida Keys-themed trinkets).

Take a cruise

Whether you opt for a sunset sail or a full Caribbean tour, Key West is a cool spot to begin, continue or end a cruise.

Touch treasure

Step back in time to 1856 to explore a part of Key West’s maritime heritage at the Key West Shipwreck Treasure Museum. Climb a 65-foot lookout tower, touch a bar of silver from 1656 and see other artifacts from the shipwreck of the Isaac Allerton.

Eat street food

Key West is a highly walkable place. Stop for a street-side snack at Pescado, which serves fresh seafood dishes like the Key West pink po’ boy, with lettuce, tomato, marinated onions and chipotle mayonnaise and a side of fries and coleslaw, washed down with tamarind tea or key limeade; Garbo’s for tacos, burritos, burgers and hot dogs; or Clemente’s, a wood-fired pizzeria housed within a San Francisco trolley car that serves thin-crust Neapolitan pizzas.

Explore the Dry Tortugas

 Aerial view of Fort Jefferson in Dry Tortugas National Park, Key West
Fort Jefferson, a six-sided fort situated in the Dry Tortugas National Park, is nicknamed “Gibraltar of the Gulf of Mexico.” (Image: Andy Newman/Florida Keys News Bureau)

Located 70 miles west of Key West, Dry Tortugas National Park is a 100-square-mile park comprised of a remote cluster of seven islands. Only one percent of the national park is dry land. Accessible via a daily ferry, charter boats, private boats and seaplanes, visitors can go swimming on the beaches, snorkeling and diving offshore and explore Fort Jefferson, a 19th-century fort.

Sample spiny lobster

From August to April, “Florida lobster” appears on menus across The Keys. Since 1947, locals have dined on the signature lobster thermidor — a dish of spiny lobster medallions served with a thyme and sherry sauce with wild mushrooms and baked with herb-infused panko breadcrumbs — at Alonzo & Berlin’s Lobster House.

Get sporty

From kiteboarding to wave-running and parasailing, there are plenty of ways to have exhilarating fun in the waters surrounding Key West.

Stroll the Historic Seaport District

Chic cafes, dive bars and funky shops line the Historic Seaport District, a harborfront entertainment complex where shrimp boats were previously docked. It’s a popular place for lunch or dinner, as well as souvenir shopping for cruise ship passengers, visitors and locals.

Hit the links

Play a round or two of golf at Key West Golf Club, the only Caribbean-style golf course in the U.S. Designed by Rees Jones, Key West Golf Club’s 18-hole, championship-rated public course winds through lush landscape, including the eighth hole, which is situated near a field of tropical mangroves.

See underwater shipwrecks

Scuba divers at a shipwreck off Key West
See spectacular shipwrecks just offshore. (Image: Joe Berg/Florida Keys News Bureau)

Numerous diving charters offer guided tours of the Florida Keys Shipwreck Trail, a trail of nine intentionally sunk vessels that stretches from Spiegel Grove, a Navy landing ship dock off Key Largo to the USNS Gen. Hoyt S. Vandenberg, an ex-military missile-tracking ship sunk off of Key West.

Step back in time

Built by Captain John Huling Geiger in the 1840s for his family, the Audubon House and Tropical Gardens is a cool place to step back in time. Visitors can tour the home to see how a wealthy maritime pilot and wrecker once lived.

Board a U.S. Coast Guard Cutter

Tour the U.S. Coast Guard Cutter Ingham Maritime Museum, a national memorial to Coast Guardians who were killed in action in World War II and Vietnam. It’s the only Coast Guard cutter afloat today to received two Presidential Unit Citations for extraordinary heroism in action against an armed enemy.

Visit the Little White House

Exterior of Harry S Truman's Little White House, Key West
Harry S. Truman began visiting the island for rest and relaxation in 1946. He returned for 175 days during his presidency. (Image: Andy Newman/Florida Keys News Bureau)

Initially a naval station’s command headquarters during the Spanish-American War, World War I and World War II, the Harry S. Truman Little White House served as the winter White House for President Harry S. Truman. Today, it’s a museum packed with historical artifacts. 

Learn about sea turtles

Open seasonally, the Key West Turtle Museum explains Key West’s maritime history through interactive exhibits and events and recounts the story of how sea turtles were driven to the brink of extinction in The Keys.

Look for dolphins

Hundreds of dolphins live off the shores of Key West. Book a dolphin safari for the chance to see dolphins jump and swim in the azure waters off Key West.

Go to the theater

Key West has a bustling theater scene. Catch a show most nights of the year at the Waterfront Playhouse, Red Barn Theatre, Tennessee Williams Theatre or Key West Theater.

Get cultured

Aerial view of Key West Harborfront
The Key West, Florida harborfront includes many attractions. (Image: Andy Newman/Florida Keys News Bureau)

Learn about the history and culture of Key West through art, architecture and history exhibits at the Key West Museum of Art & History at the Custom House.

Try on Kinos

Since 1966, this sandal factory has handcrafted leather sandals beloved by locals and visitors alike. In a place with a come-as-you-are attitude, sandals like those at Kino Sandals are the preferred footwear here.

Visit The Oldest House

Located at 322 Duval Street, visitors can tour The Oldest House for free. The house features original furnishings, ship models and family portraits from Captain Francis Watlington, his wife Emeline and their nine daughters who lived in the home. The property also boasts the only surviving cookhouse in South Florida.

Walk among butterflies

Head to the Key West Butterfly and Nature Conservatory, a butterfly park home to 50-plus species of butterflies, including Owl butterflies, which are the largest butterfly at the park, and seasonally, the Atlas moth, the largest moth in the world.

Drive the Overseas Highway

View from a car driving on the Overseas Highway
The Overseas Highway connects the Florida Keys to the South Florida mainland. (Image: Andy Newman/Florida Keys News Bureau)

Named an All-American Road, the Overseas Highway is not only the way to travel from key to key, but is also the perfect spot for watching mesmerizing sunrises.

Eat conch

In a place called the Conch Republic, it’s no surprise that most restaurants have conch on the menu, prepared in a myriad of ways. Head to Sharkey’s for conch fritters — chopped conch meat battered and seasoned with cayenne pepper, bell pepper, celery, garlic and salt, then deep fried — and conch chowder, a spicy, tomato-based comfort food brimming with diced onions, celery, carrots, tomatoes, potatoes, and conch meat. Conch Republic Seafood Company is another great choice for trying this local favorite.

Get sand in your toes

Located where the street meets the beach, knock back some cold ones at Lagerheads Beach Bar. The laid-back beach bar offers sand-in-your-toes dining right on the beach. Pull up a chaise lounge, hop on the bar’s Panama Jack Rum Boat or just sit in the sand and soak up the sun.

Explore the ecosystem

Family at the National Marine Sanctuary at the Florida Keys Eco-Discovery Center
Through a series of interactive exhibits, the $6 million Eco-Discovery Center showcases the Florida Keys National Marine Sanctuary’s environment. (Image: Andy Newman/Florida Keys News Bureau)

Learn about the diverse ecosystem in the Florida Keys at the Florida Keys Eco-Discovery Center. Museum-goers are transported through upland pinelands, hardwood hammocks and beach dunes and through seagrass flats and coral reefs.

Go fish

Another favorite pastime of Hemingway’s,  game fishing on the Florida Straits, a 90-mile trough of deep water, is still a popular activity today. Charter guides lead anglers to snapper, grouper, billfish and more on daily game fish excursions.

Go (coco)nuts

Chocolate covered coconut candy is a ubiquitous staple at most shops in Key West. Be sure to sample these sweet shredded coconut patties enrobed in chocolate.

Get artsy

Forgo the typical souvenirs and stock up on local art instead. Just stop by the Guild Hall Gallery, a co-op with 27 artist display spaces where local artists display and sell their art, from pastel painted scenes to sea glass jewelry.

What’s the first thing you would do in Key West? Let us know in the comments and search for flights at Cheapflights.com

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Main image: iStockPhoto/lucatelles

52 super cool things to do in Key West was last modified: May 22nd, 2017 by Lauren Mack
Author: Lauren Mack (265 posts)

Lauren Mack has traveled to 40 countries on five continents, including Cuba, New Zealand, Peru and Tanzania. For many years, she called China, and then Taiwan, home. Countries at the beginning of the alphabet, particularly Antarctica, Argentina and Australia are on her travel bucket list. Lauren is a multimedia travel and food journalist and explorer based in New York City.