It’s all part of the experience in the Florida Keys, a necklace of more than 1,700 islands stretching southwest from Miami to just 90 miles north of Cuba. Couples, families, and solo travelers can drive the Overland Highway that connects the five main areas of Monroe County and experience endless adventures--followed by a piece of Key lime pie, of course.
Here’s how to have five perfect days as you make your way across the Keys.
Day 1: Key Largo
The longest island in the Keys—and the inspiration for the 1947 movie of the same name—is a great place to get acclimated to island life. Head out with a charter boat captain and cast for bonefish. Take to the water yourself by snorkeling or diving among the sea turtles, pelicans, and mangroves in America’s first undersea park, John Pennekamp Coral Reef State Park. Begin your nightly routine of winding down with sunset drinks at a beachside cafe, then sample some of the islands’ unique cuisine, like conch fritters and conch chowder, at a laid-back spot like Alabama Jack’s.
Day 2: Islamorada
Anglers will feel right at home in Islamorada—a place where backcountry sport fishing and saltwater fly fishing were pioneered. One of the island’s experienced captains can take you into the bay or ocean to cast for an astounding assortment of creatures, like sailfish, marlin, kingfish, and tuna. Learn about early inhabitants at the Keys History & Discovery Center, then watch dolphins and sea lions perform at the Theater of the Sea. And don’t miss out on a Rum Runner cocktail at the home of its invention—the Tiki Bar at the Postcard Inn.
Day 3: Marathon
Ten-mile-long Marathon Key is best known as a family destination steeped in the traditions of Old Florida, but every type of traveler can find their place here—especially animal lovers. Start by meeting the endangered sea turtles being rehabilitated at the Turtle Hospital, go swimming with dolphins at the Dolphin Research Center, then feed the fish (as well as the sharks!) at the Florida Keys Aquarium. When you’re ready to relax, hit the soft sand of Sombrero Beach and swim in the warm, turquoise waters. Then dig into a piece of Key lime pie at Sweet Savannah’s Bake Shop before enjoying another magical Florida Keys sunset.
Day 4: Lower Keys
Nature rules in the Lower Keys, where travelers will discover a plethora of parks. Ride bike through the National Key Deer Refuge to see a species of deer found nowhere else on earth. Then spread out a towel on one of America’s most beautiful beaches in Bahia Honda State Park. Close the day at a waterside restaurant, where you can tuck into fresh, locally harvested fish like lobster and stone crab. And if you’re an adventurer who loves to camp, this is the place to do it.
Day 5: Key West
While romance flows throughout the islands, Key West could well be its epicenter. This mini-melting pot combines all sorts of cultural influences, from Afro-Caribbean to LGBTQ, and adds colorful gingerbread houses as well as a dash of history at the former home of Ernest Hemingway. Wander through the area’s many galleries and visit the butterfly conservatory. Marvel at the chickens and cats that roam the Blue Heaven restaurant. Then prepare yourself for what may be the most festive sunset celebration in the Keys, at Mallory Square, before things really heat up at the bars and clubs. It’s an ideal finish to an unforgettable five days in the Florida Keys.
