One Of Florida's Most Overlooked Islands Offers A Laidback Escape From Crowds Into Nature

In the wise words of Taylor Swift, "I need to forget so take me to Florida." No matter what kind of traveler you are, the Sunshine State is one of the best places to abandon your worldly worries and indulge in a peaceful escape. It's home to many iconic theme parks, a lively party scene, gorgeous natural wonders, white sand beaches with crystal clear waters, and island adventures you don't need a passport for. The state is also host to some of the most underrated tropical experiences. If you're looking to mix a history lesson into your vacation, a visit to Chokoloskee Island is a must.

This small island at the end of a road in the Everglades houses an unincorporated community of about 350 residents and has more history than many major U.S. cities. Chokoloskee Island is known by many as one of the last frontiers in the region and is a popular retirement location for local mainlanders. It offers a quiet and peaceful retreat from popular and often overstimulating tourist attractions. There is much for travelers to discover and explore, so head over the Tamiami Trail to avoid crowds and relax in this historic town in Florida.

Present-day Chokoloskee Island is home to a small and quaint community that centers on fishing and relaxation, but its beginnings weren't quite as wholesome. The land remained untouched by Western civilization for over 2,000 years and instead served as a home to the Calusa, Miccosukee, and Seminole tribes. The first white settlers arrived in 1847, and by the end of the century, five families inhabited the island. Calusa Natives were either driven off the land, killed by disease brought by settlers, or assimilated into the new society.

Until recently, the island remained isolated and was only reachable by sea, making it a prime location for nefarious activities, such as housing illegal shipments of moonshine. This also made the island a perfect hideout for runaway criminals and outlaws. Perhaps the most famous of these was alleged serial killer Edgar J. Watson. He escaped conviction by hiding away on the island as a sugar farmer, but despite his efforts, trouble continued to follow him. He often got into altercations with local workers and was even accused of murdering some of them. In 1910, he was shot and killed by local residents. Despite its sketchy past, Chokoloskee Island is now a charming destination that offers unique experiences you can only have in Florida.

Don't let size fool you, as there is so much you can do on Chokoloskee Island. Since fishing is the main draw of the region, visitors shouldn't miss out on locally-owned fishing tours that go deep into the Everglades and Ten Thousand Islands, which are some of the best ways to spot alligators in the Everglades. Most other activities also revolve around the water, such as kayaking, canoeing, paddleboarding, and boating.

If dry land is more your forte, you can spend time in some of the historic buildings around town and learn more about the island's past. One of the best places to do this is Smallwood's General Store, which is on the U.S. National Register of Historic Places. This site — run by the Smallwood family — was established in 1906 and now serves as a museum. Step inside to learn more about the native tribes that inhabited this region over 2,000 years ago. If you're a true crime girly, the general store is also where you'll find the "Bloody Watson Tour," which gives you a look into the life of the alleged serial killer.

If you plan on an overnight stay, you'll be delighted to know that all lodging options are close to the water. Book a lot at the local RV resort or rent a cozy cabin. When you're hungry, enjoy fresh seafood options at the various restaurants across the island. At the end of a long, sit by the water and reflect on your relaxing, stress-free vacation.