Escape to Florida’s Island Paradise

Key West 

This fun and funky island, the southernmost point you can drive to in the United States, is the unofficial cultural hub of The Keys. It’s famous for its resident artists as well as its annual celebrations, like Fantasy Fest, which culminates in a parade on the last Saturday of October. A stop at the Hemingway Home and Museum is a must; there you’ll learn about the author’s life on and off the island and have a chance to see one of Hemingway’s six-toed cats.

Key West’s Old Town, filled with an eclectic mix of more than 3,000 wooden buildings, is the largest historic district recognized by the National Register of Historic Places. Hop on the Old Town Trolley and you’ll be guided through highlights, from former cigar factories and speakeasies to the southernmost point in the United States and Harry S. Truman’s “Little White House.”

The Lower Keys

This tangle of quiet islands between Marathon and Key West offers a tranquil escape known for small-town vibes, scenic bridges, and preserved land and marine refuges. The Lower Keys are surrounded by pristine, protected waters—ideal conditions for exploring life beneath the surface. The 524-acre Bahia Honda State Park makes for an easy entry into snorkeling. You can rent all the gear you need from the local concessionaire and then enter the water directly from the beach to find coral heads, tropical fish, and conch close to shore in just a few feet of water.

If you’re seeking something more adventurous, set out nine miles west of Bahia Honda State Park for the Looe Key Sanctuary Preservation Area, home to one of the world’s largest reefs and a variety of live corals you can explore. The marine life is diverse, with parrotfish, surgeonfish, angelfish, barracudas, and jacks all calling the ecosystem home. Local charters run trips to the reef daily.

Marathon

One of the greatest experiences you can have in The Keys is catching a fish in the afternoon, then having a professional chef cook it for you that very evening. Marathon is a great place to do exactly that, at Florida Keys Steak and Lobster, which specializes in cooking your very own catch, which the chefs will prepare either broiled, grilled, or fried and round it out with two sides.

The ten-mile-long community, made up of 13 separate islands, has plenty of other options if you’re not an angler but still want fresh fish. Hit Castaway Waterfront Restaurant, which offers a variety of prepared local seafood as well as fresh ceviche and sushi. Need a burger instead? Burdine’s Waterfront Bar and Grill serves its burgers above an active marina with a coastal view that stretches for miles.

Islamorada 

Known as the sportfishing capital of the world, the six islands that make up Islamorada boast fast access to some of the most fertile fishing waters in North America, with anglers reeling in the most sought-after game fish in the world, from tarpon to bonefish. There’s so much fishing surrounding Islamorada, it can be hard to know exactly where you should focus your efforts. First, pick your fish, then home in on a location. If you’re looking to catch wily redfish, snook, or trout, you’ll want to head to Florida Bay’s backcountry, where you can hunt for these feisty species using light tackle and fly rods on small boats that can cruise through shallow water. Captain Steve can put you in the right place with the right gear to land the fish you’re looking for.

Want to catch a big one (or two)? Head to deeper water, specifically the Islamorada Hump, an underwater mountain that rises to within 290 feet of the surface, attracting massive tuna and mahi mahi. Hire a pro to get you there for the best chance to land that big fish of your dreams.

Key Largo 

The first island you reach from the mainland, Key Largo acts as a gateway to the greater Keys and is renowned in its own right for its lush, tropical forest and public land, boasting two state parks as well as portions of a national park and national marine sanctuary.

In fact, you could spend your entire trip to Key Largo bouncing from one outdoor adventure to the next. If you’ve always dreamed of the open sea, spend three days learning to sail a Catalina 22 at the American Sailing Academy, then borrow one of the school’s boats for your own adventure after completing the course.

Amateur botanists and animal lovers should hike the trails of Dagny Johnson Key Largo Hammock Botanical State Park, home to a West Indian hardwood hammock that protects more than 80 protected species, from wild cotton to the American crocodile. And no trip to Key Largo is complete without paddling Tavernier Creek, where you might spy manatee, turtles, and stingray from the deck of your paddleboard. With such a close connection between land and sea, it’s no surprise Key Largo is home to dolphin therapy, one of the most unique wildlife experiences in the world. The nonprofit Island Dolphin Care provides therapeutic encounters for military vets and people with special needs, as well as experiences for all visitors. Every morning, guests have a chance to meet the pod of dolphins that live in the center. You can even sign up for a yoga class with the dolphins.

Most people know the Florida Keys and Key West as a great escape to one of the most unique places on earth. Calm. Serene. Laid back. Just the right setting to recharge your batteries and rejuvenate your spirits. But a getaway to the Florida Keys and Key West is much more than peace and quiet. And not just because of the legendary fishing and the world’s most spectacular dive sites. The Keys mean history. Art. Theater. Museums. Shopping. Fine dining. Entertainment. And much more. All told, 120 miles of perfect balance between natural beauty and extra-ordinary excitement.