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27 Top Things To Do On Your Florida Keys Vacation

When it comes to vacation getaways, Florida spoils us with options, whether you’re the type who pines for a cosmopolitan city or vast areas of white-sand beaches. But when you live in the land of vacation, where do you go for your escape? For many Sunshine Staters, the answer is the Florida Keys.

The appeal of this laid-back paradise isn’t so much about the beaches (though there are plenty of them). It is the feeling of escaping to an undiscovered utopia. Water surrounds you in what seems like a million shades of blue in the Florida Keys. Nearly every wrong turn leads you to a shady swimming hole with views for miles, and if you venture out into the wild blue yonder, the underwater coral kingdoms are teeming with color and sea life. But while it may feel otherworldly in its beauty and seclusion, the real magic of the islands is their accessibility. Fly into Miami in the morning, and you can be island-side chowing down on a fresh mahi mahi sandwich by lunch.

With year-round balmy temperatures, the Keys draw tourists near and far every season. In wintertime, crowds descend, searching for the sweet spot in favorable temps and low humidity. But you’ll find the best deals in late spring or summer (if you can handle the sticky heat). The same rings true for fall, but beware of hurricane season (most active between August and October), and be prepared with a backup plan should the weather damper your getaway. Now that you’re ready to visit paradise, here are some of the best things to do in the Florida Keys.

Drive The Overseas Highway

Reese Lassman / EyeEm / Getty Images

Spilling out south from the Florida peninsula, this dreamy archipelago forms a beauty trail comprising hundreds of (mostly uninhabited) islands. The Overseas Highway connects 44 islands, a 113-mile road from Key Largo to Key West—the most famous among the bunch. While each island is a worthy destination, the draw here is in the journey. While heading south, you’ll leapfrog from island to island via a whopping 42 bridges. Make it to the end—with character-filled Key West as its grand finale, you’ll definitely want to—and you’ll be closer to Cuba than the Florida mainland.

Stay On Dreamy Key Largo

Courtesy of Bungalows Key Largo

Key Largo, Florida

The beauty of the Florida Keys is that, with an entire length that takes just over two hours to drive (if you’re beelining it), you don’t have to park in just one place. Each island has its perks and personality, from laid-back Islamorada to the funky and, at times, raucous Key West. For the ultimate getaway, kick back and get some sun at the Bungalows Key Largo, an adults-only all-inclusive resort with alfresco soaking tubs, waterfront dining, and Zen Garden Spa.

bungalowskeylargo.com, 99010 Overseas Highway, Key Largo, FL 33037

Dive In An Underwater Park

Stephen Frink/Getty Images

Key Largo, Florida

Kick off your Keys journey at the chain’s first and longest island, offering 33 miles of sun-drenched beauty and an underwater dreamland that attracts explorers from across the globe. As the self-proclaimed Dive Capital of the World, Key Largo is home to an impressive reef system that includes John Pennekamp State Park (the first underwater preserve in the U.S.) and the U.S.S. Spiegel, a 510-foot landing ship dock—intentionally sunk to create one of the world’s largest artificial reefs. Pennekamp Park also offers glass-bottom boat tours and kayak rentals if you prefer to stay a little dryer while witnessing the area’s aquatic wonders.

pennekamppark.com, 102601 Overseas Highway, Key Largo, FL 33037

Enjoy The Sportfishing Capital Of Islamorada

romrodinka/Getty Images

Islamorada, Florida

Venture further south into the turquoise abyss, and you’ll hit Islamorada, a village of six islands beloved for its laid-back feel and sweeping vistas (it’s starred in a few Hollywood productions, including Netflix’s Bloodline). Within the “Sportfishing Capital of the World,” leaning palms frame views of calm blue-green waters dotted with activity—boats, paddlers, kayakers, and swimmers. Islamorada is the perfect place to splash around yourself. From kiteboards to wave runners, the island offers multiple places to grab a rental.

Sunbathe On Sombrero Beach

Simon Dannhauer / Getty Images

Marathon, Florida

Right around the halfway point in the archipelago, you’ll hit Marathon, a quiet little city comprising 13 separate islands. Now’s your chance to cash in on that R&R—Sombrero Beach is one of the best sandy shorelines. When you’ve had your fill of surf and sun, get schooled on some of the Keys’ native wildlife. When you work up an appetite, Keys Fisheries is a must-stop whether you’re parked for a few nights in Marathon or just passing through.

ci.marathon.fl.us, Sombrero Beach Road, Marathon, FL 33050

Get Back To Nature On Big Pine Key

John Duarte/Getty Images

Big Pine Key, Florida

If you’re here for nature and could do without the crowds, Big Pine and the Lower Keys are great places to settle in. Roughly 30 miles north of Key West, the islands are rife with low-key activity both on water and land, yet a quick (and beautiful) drive to all the action. Bahia Honda State Park offers it all—swimming, camping, fishing, boating, excellent birding, and even a hike that drops you off at the top of the Old Bahia Honda Bridge (with a bird’s eye view of the entire island). Also on Big Pine Key, the National Key Deer Refuge provides a home to more than 20 endangered and threatened plant and animal species.

floridastateparks.org, 36850 Overseas Highway, Big Pine Key, FL 33043
fws.gov, 30587 Overseas Highway, Big Pine Key, FL 33043 

Shop On Duval Street

romrodinka/Getty Images

Key West, Florida

You’ve reached the end—but things aren’t slowing down. Measuring little more than seven square miles, famous Key West (once home to authors Ernest Hemingway and Tennessee Williams) has all the makings of a dynamite vacation—beaches, history, food, sunsets, and some great bars. Once you post up at home away from home, ditch the car in favor of two wheels and go out and explore the endless shops on Duval Street.

Stay On A Private Island

Little Torch Key, Florida

This adults-only resort is pure magic and probably the top reason people travel from all over the country—and the world—to visit Little Torch Key. As the only private island resort in the entire U.S., Little Palm Island Resort offers an experience unlike any other. Reachable only by sea plane or boat, the 4-acre property features 15 thatched-roof bungalows, each housing two separate suites with every amenity imaginable. We’re talking copper soaking tubs, outdoor showers, furnished decks, fire pits, private gardens, and sweeping views of the ocean. The resort is all about helping visitors unwind and unplug, which is why there are no TVs in bedrooms, but there are complimentary snorkel, kayak, paddle board and boat rentals, as well as a world-class spa.

littlepalmisland.com; 28500 Overseas Highway, Little Torch Key, FL, 33042;

Feed The Tarpon At Robbie’s

Danita Delimont/Getty Images

Islamorada, Florida

This legendary Florida Keys spot is a hub for all things island-themed fun. Feed the famous giant tarpon right off the docks, hop aboard Captain Michael’s party fishing boat, rent a kayak, or take a snorkeling tour. If you prefer to stay on land, snag a seat at Hungry Tarpon Restaurant where you can dine with a view of the water from sunup to sundown.

robbies.com, 77522 Overseas Highway, Islamorada, FL 33036, United States

Explore The Rain Barrel Village

Courtesy of Rain Barrel Village

Islamorada, Florida

Another iconic Keys spot, folks have been flocking to Rain Barrel Village for decades to browse local art and take a picture with the enormous Betsy the Lobster. Just walking through the colorful galleries and open-air shops of this tropical oasis is enough to put you on island time. The cocktails and live music at the onsite bar only add to the festivities.

rainbarrelvillage.com, 86700 Overseas Highway, Islamorada, FL 33036

Visit Hemingway House

Petr Kahanek/Getty Images

Key West, Florida

With so much history on Key West, you’ll find plenty of museums to explore. A must-see attraction is the Ernest Hemingway Home & Museum in the heart of Old Town Key West. Wander through the Nobel Prize winner’s lushly landscaped property and make friends with one of the six-toed cats, most descended from a cat the famous writer was gifted by a ship’s captain.

hemingwayhome.com, 907 Whitehead Street, Key West, FL 33040

See The Sunset Celebration At Mallory Square

Bob Krist/Florida Keys News Bureau

Key West, Florida

Mallory Square is the hot spot to catch the sunset along with great entertainment. The nightly sunset celebration starts two hours before the sun goes down. On any given night, you can watch magicians, jugglers, clowns, psychics, local musicians, artists, and more.

mallorysquare.com, 400 Wall St., Key West, FL 33040

Learn About Turtle Rescue

Courtesy of VISIT FLORIDA

Marathon, Florida

Learn all about sea turtle rescue and take a tour of the tanks and rehab facilities at The Turtle Hospital in Marathon. The hospital also schedules occasional public releases of rehabbed turtles, with the opportunity to cheer on our flippered friends as they make their way back to the water.

turtlehospital.org, 2396 Overseas Highway, Marathon, FL 33050

Barhop In Key West

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Key West, Florida

Whether it’s a tiki bar on the waterfront, a favorite haunt of Ernest Hemingway, or a dive bar where Jimmy Buffett played, you’re sure to find something that suits your taste in Key West. Try not to hit all the bars on one night, because there are more than 40 on Duval Street alone. If you’re overwhelmed by the options, book a guided tour with Duval Crawl, “the ultimate Key West Tradition.”

Visit Fort Taylor

Getty Images / Paul Harris

Key West, Florida

Built in the 1860s to defend Florida’s southern coast, Fort Zachary Taylor played a role in both the Civil War and the Spanish-American War. This historical site has a large collection of cannons and offers guided tours and re-enactments on the third weekend of each month. The fort is surrounded by the natural beauty of a state park, with opportunities for swimming, snorkeling, paddling, and fishing.

floridastateparks.org, 601 Howard England Way, Key West FL 33040

Swim With Dolphins

© Photographer, Debbie Speak/Getty Images

Grassy Key, Florida

Next door to Marathon, Grassy Key is home to the Dolphin Research Center, a research facility and forever home for dolphins and sea lions that can’t be released back to the wild. Visit to learn more about these charismatic creatures or schedule a dolphin encounter and swim alongside them.

dolphins.org, 58901 Overseas Highway, Grassy Key, FL 33050

Hike The Old Seven Mile Bridge

FilippoBacci / Getty Images

Marathon, Florida

Originally built by railroad magnate Henry Flagler to connect Miami to Key West, dreams of bringing the rail this far south were eventually destroyed in the 1930s by a hurricane. The bridge was closed to cars after the state of Florida opened a new bridge beside it in 1982. Recently, a portion of the Old Seven was restored and reopened, allowing walkers and bikers to travel over the water from Marathon to Pigeon Key, the tiny island underneath the bridge where railroad workers once lived. It’s worth walking over to see the railroad museum and structures that date back to the early 1900s. You can also take a “train” from the Pigeon Key Visitor’s Center in Marathon.

pigeonkey.net, 1090 Overseas Highway, Marathon, FL 33050

Drink A Brew At No Name Pub

Courtesy of No Name Pub

Big Pine Key, Florida

This Florida landmark started out as a general store and bait-and-tackle shop in the 1930s, and the bar has remained “A Nice Place If You Can Find It,” per its catchphrase. The legendary pizza recipe, which dates back nearly 60 years, is preserved on the kitchen wall.

nonamepub.com; 30813 Watson Boulevard, Big Pine Key, FL 33043

Sample Key Lime Pie

Courtesy of Key Lime Pie Company

The iconic dessert of the Florida Keys can be found everywhere, giving you plenty of opportunities to taste test your way across the islands. Our readers have named their favorites and we suggest giving at least one of these establishments a try.

Travel To Dry Tortugas

Garden Key and Fort Jefferson in Dry Tortugas National Park, Florida.
Posnov / Moment / Getty Images

Depart from Key West, Florida

For a truly memorable beach day in a national park, book a ferry boat or seaplane ride out to the remote Dry Tortugas National Park. The 100-square-mile park consists of seven islands in the Straits of Florida, including Garden Key, where you can explore historic Fort Jefferson. The 1875 Windjammer wreck off of Loggerhead Key is a popular dive site.  Ferry rides through Yankee Freedom depart early in the morning and return to Key West by dinnertime.

nps.gov

Steam On The African Queen

© Joe Raedle/Getty Images

Key Largo, Florida

The African Queen was built in England in 1912 to service the East Africa British Railways company. The steamboat became famous when it was commissioned to star in the 1951 movie of the same name along with Humphrey Bogart and Katherine Hepburn. Film buffs can take one of the daily canal cruises on the original steamboat through Port Largo.

africanqueenflkeys.com, Marina Del Mar, 527 Caribbean Dr., Key Largo, FL 33037

Stop At The Florida Keys Wild Bird Center

The Laura Quinn Wild Bird Sanctuary.

Mom 4 a Difference 

Tavernier, Florida

This sanctuary serves as a refuge for dozens of birds that aren’t able to survive in the wild, providing an educational opportunity for families interested in learning about wildlife (and watching pelican feedings). The beautiful 5.5-acre property stays open until sunset so you can enjoy the view.

keepthemflying.org, 93600 Overseas Highway Tavernier, FL 33070

Kayak Through The Mangroves

Kayaking through mangroves.

Alexander Robinson/ Getty

 

 

From a distance, the tangled roots of a mangrove forest can look impenetrable. The best way to see these wetland trees and the habitat they create is by kayak. Mangrove forests line more than 1,800 miles of shoreline along the Florida Keys, so there are guided trips and rentals available throughout the islands.

Visit The Key West Butterfly & Nature Conservatory

Marco Bellentani/Getty Images

Key West, Florida

Looking for a family friendly option on a rainy day? This glass-domed butterfly conservatory is one of the most popular stops in Key West. Inside you’ll find lush foliage, hundreds of butterflies, and tropical birds including two strutting flamingoes. The conservatory is open to visitors 365 days a year.

keywestbutterfly.com, 1316 Duval St., Key West, FL 33040

Travel To An Abandoned Island

felixmizioznikov/Getty Images

Indian Key, Florida

This small uninhabited island has a fascinating history dating back centuries. During its brief time as a private island in the 1830s, Indian Key had a store, hotel, homes, and warehouses. Later, it was used by the US Navy for military garrisons. Today it’s a state park open to daytime visitors who reach it by kayak or boat, though there are no public facilities on the island. Paddle over during high tide from Islamorada to explore the trails and ruins.

floridastateparks.org

Sip Cuban Coffee

Hector Manuel Sanchez

Key West, Florida

With Key West’s close proximity to its southerly neighbor, it’s no surprise the island has become known for fresh-brewed Cuban coffee. Closer to espresso than American coffee, Cuban coffee is often brewed with sweet cane sugar. Stop at one of the Cuban Coffee Queen’s three locations for cafe con leche served with traditional toasted bread for dunking, or enjoy a cup of joe with a Cuban sandwich.

cubancoffeequeen.com, Key West, FL

Drink A Rum Runner

Richard Boll / Photographer’s Choice RF / Getty Images

According to legend, the original rum runner was invented by John Ebert, also known as “Tiki John,” at the Holiday Isle Tiki Bar in Islamorada more than 40 years ago. Unfortunately, the original tiki bar is long gone, but you can still enjoy the iconic rum cocktail, infused with orange and banana liqueur, all over the Keys.

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Publish date : 2024-07-11 03:00:00

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