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The windows are down, the salty air is dancing in your hair and the warm Florida sun is kissing your cheeks. Surrounded by clear, turquoise waters and 106 miles of road ahead, you embark on a summer road trip through the Florida Keys.

The Overseas Highway, sprinkled with sandy beaches, kitchy shops and seafood shacks begins in Key Largo, right off the shores of Florida, and ends in Key West, a delightfully colorful, tropical city with legendary happy hours, shopping, art galleries and sunsets.

To make the most of your road trip to Key West, we’ve made a list of must-see stops along the way.

Key Largo

Key Largo is home to the John Pennekamp Coral Reef State Park, the first undersea park in the United States. If you don’t want to get your toes wet just yet, view the reef from a glass-bottom boat or get up-close and personal with the marine life by scuba diving or snorkeling. From the depths below, explore the coral reefs and sunken shipwrecks. An underwater statue, Christ of the Deep, welcomes divers to the Dive Capital of the World.

An underwater statue, Christ of the Deep, welcomes divers to the Dive Capital of the World.


Islamorada, Spanish for “purple island,” is just bout 20 minutes down Oversea Highway and is a sport-fishing mecca. The warm Gulf waters are home to tarpon, sailfish, spotted sea trout, snook, redfish, largemouth bass, panfish, grouper, snapper and mackerel.

Visitors are able to feed the tarpons, which can grow to more than eight feet long and up to 350 pounds, from a local dock. The “silver kings” may jump out of the water and create quite a splash. While the massive fish will catch your eye with their iridescent scales, be sure to use precaution—after all, they are wild!


Looking to get some spectacular sunset photos? The Seven Mile Bridge is the Florida Keys’ longest bridge and is now wide enough to pull to the side and take pictures or just enjoy the view. But Marathon isn’t worth the stop for just the bridge—The Turtle Hospital rescues, rehabilitates and releases endangered sea turtles. Since its founding in 1986, the hospital has successfully treated and released more than 1,500 sea turtles.

Educational programs run daily, allowing visitors to take a behind-the-scenes tour of the hospital facilities and the sea turtle rehabilitation area. At the end of each tour, guests are able to feed the resident sea turtles.

Big Pine

Thirty minutes down the road is Big Pine Key, which is part of the Lower Keys. What you might not expect to find roaming in the shallow bays are deer. The endangered Key Deer is the smallest subspecies of the North American white-tailed deer. While the deer might feed on over 150 species of native plants, these deer only get to about knee height, making them ultra-cute. Be sure to drive slowly to catch a glimpse of these little ones on the side of the road and while they may come up to you for a visit, don’t feed the wildlife.

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Key West

At last, the final destination: Key West, the southernmost city in the continental US. Whether you prefer lots of activity with kayaking, parasailing, boating and biking or want to stroll through a butterfly refuge or Ernest Hemingway’s home during the day, Key West has got it.  But don’t think festivities end once the ocean swallows up the sun.

Start your evening in Mallory Square with the Key West Sunset Celebration, which overflows with magicians, jugglers, clowns, psychics, musicians, artists, and food vendors. With seemingly never-ending happy hours, your evening has only begun. Grab a cocktail and enjoy a laid-back evening with a live jazz band or slip on your dancing shoes and shimmy into the night.

Key Events

Key West Tropical Heat, August This event for gay men includes theme parties and pool parties for anyone who likes to party.

Womenfest Key West, September This event for gay women welcomes friends from across the globe to an annual celebration over Labor Day weekend.

Key West Pride, June Celebrate Pride on a tropical island in one of the most integrated and accepting communities on the planet.


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