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9 Ultimate Weekend Road Trips You Can Take from Major US Cities

5 Best Weekend Getaways from Key West


Palm trees in Miami Beach, Florida
Hi, I'm Emma!

Emma Knock is a Melbourne-based writer and editor who arrived in Australia from London after a half-a-decade stint in California and Aotearoa. Find her between the stacks at your local bookstore or planning trips over flat whites.

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There’s four square miles of paradise on the southern tip of Florida where sunshine, Afro-Caribbean cuisine, water sports, and candy-colored conch houses can be found in abundance. But if you’re lucky enough to call this tropical nirvana otherwise known as Key West home, chances are you’re ready for a change of scenery after months of sheltering in place. From Key Largo’s underwater sights to Naples’ sugar-sand beaches—and the swamplands in between—here’s our pick of the best weekend getaways from Key West.


Key Largo

Boats docked outside houses in Key Largo, Florida
Boats docked outside houses in Key Largo, Florida. Photo: Christian Ochoa / Unsplash

Drive time from Key West: 2 hours / 100 miles (161 kilometers)

You’d be forgiven for thinking there’s not much to see in Key Largo, but look closer (or more specifically, under the water) and you’ll understand why the Beach Boys sang about it in “Kokomo.” One of the world's diving capitals, Key Largo is home to an underwater state park, coral reefs, and the only underwater hotel in the US. John Pennekamp Coral Reef State Park, Dagny Johnson Key Largo Hammock Botanical State Park, and Key Largo National Marine Sanctuary are three places rarely left of any Key Largo itinerary. Diving and snorkeling aside, joining a kayak or SUP eco tour or glass-bottom cruise are great ways to explore without getting too wet.

Pro tip: Pick up a slice of key lime pie from Mrs. Mac's Kitchen.

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Miami

Neon signs and art deco buildings in Miami, Florida
Neon signs and art deco buildings in Miami, Florida. Ryan Spencer / Unsplash

Drive time from Key West: 3.5 hours / 170 miles (274 kilometers)

Palm-fringed beaches, Cuban influences, sunrise-to-sunset nightlife, and art deco everything—Miami is both a cultural hub and a prime beach destination. Make time to explore the South Florida city’s neighborhoods: Head to Wynwood for street art and third-wave coffee; South Beach for rooftop bars, clubs, and the Art Deco Historic District; and Little Havana for the best Cuban food you’ll ever eat. And no trip to Miami would be complete without a day at the beach or out on the water.

Related: Top Beaches in Miami

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Everglades National Park

A snowy egret in Everglades National Park, Florida
A snowy egret in Everglades National Park, Florida. Alex Shutin / Unsplash

Drive time from Key West: 3 hours / 140 miles (225 kilometers)

Everglades National Park is a popular day-trip destination, but stop and stay awhile and you'll find a multitude of reasons to keep returning to its green swath of forests, mangroves, and estuaries. Airboat is one of the best—and most popular—ways to explore the largest subtropical wilderness in the US. There’s also an array of great hiking and biking trails, including the Shark Valley, Anhinga, and Gumbo Limbo trails. Pitch your tent at Long Pine Key Campground or Flamingo Campground (both drive-in locations), or if camping isn’t really your thing, base yourself in the nearby town of Homestead.

Related: How to Spend 3 Days in Everglades National Park

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Big Cypress National Preserve

An alligator spotted up-close in Florida
Alligator sightings are common along Big Cypress' Loop Road. Photo: Allison Christine / Unsplash

Drive time from Key West: 4 hours / 200 miles (322 kilometers)

Just north of the Everglades lies Big Cypress National Preserve. Here you can wander designated trails or uncharted territory, go off-roading, and explore swamplands by airboat—all with fewer crowds and more wildlife than you’ll find further south. For an easy introduction to the wilderness, drive the Loop Road, stopping along the way to observe wildlife from the boardwalks. Big Cypress Swamp Welcome Center and Oasis Visitor Center are also great locations for viewing alligators and less commonly manatees. To get even further off the beaten path, secure a backcountry permit and camp along the way on a kayaking or canoeing adventure.

Read more about Big Cypress National Preserve

Naples

Sunset at Naples Pier, Florida
Naples Beach and Pier is a popular spot for sunset. Photo: Bailey Rapp / Unsplash

Drive time from Key West: 5 hours / 240 miles (386 kilometers)

Mangroves, manatees, and Marco Island. These three Ms are the not-so-secret ingredients to a successful trip to Naples, Florida. Your first order of business in Naples is to stroll along Naples Pier. Its 130-year-old boardwalk has stood the test of time, living through a fire and several hurricanes, and there’s no better place in the city to fish, spot dolphins, or watch the sunset. From there, your options are endless, but we recommend adding a manatee eco tour, Keewaydin Island shelling cruise, Marco Island dolphin cruise, and mangrove tunnel kayaking adventure to your list.

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Hi, I'm Emma!

Emma Knock is a Melbourne-based writer and editor who arrived in Australia from London after a half-a-decade stint in California and Aotearoa. Find her between the stacks at your local bookstore or planning trips over flat whites.

Keep exploring
See all Key West tours
197 tours & tickets
Things to do in Key West
See all things to do in Key West
9 Ultimate Weekend Road Trips You Can Take from Major US Cities