Chokoloskee Day Trip Adventure

Chokoloskee Island sits on the western edge of the Everglades and is known for fishing, kayaking, bird watching and other outdoor activities

Aerial view of Chokoloskee

Chokoloskee Island sits on the western edge of the Everglades, in the heart of the Ten Thousand Islands. It has been called “The Last Frontier” and is known for fishing, as well as kayaking, bird watching, and other outdoor adventures. Spend a day exploring the wonders and lore of Chokoloskee.

Chokoloskee History and Lore

Chokoloskee is a once isolated historic island in Southwest Florida. First inhabited by Native Americans for at least 1500 years, it sits 20 feet above sea level. By comparison, the surrounding area is low lying wetlands. Years of Native Americans lived off the native shellfish, creating shell mounds that give Chokoloskee its height today.

The first pioneer settlers can be traced back to 1874 to John Weeks and his family. By 1897, five families resided on the island, including Ted Smallwood. He opened a store on the south side of the island in 1906. The Smallwood Store was the site of the famous death of Edgar “Bloody” Watson, a sugar cane and vegetable farmer from Chatham Key. Some say he still resides there. The store and site still exist today, and in fact, you can take a boat tour to visit. Will you catch a glimpse of Mr. Watson? Maybe not, but at least you can pick up a souvenir at the Smallwood Store Museum.

View of the outside of the Smallwood Store


Where to Stay in Chokoloskee

The Outdoor Resorts of Chokoloskee are located on the north side of the island. Lodging consists of an eight-unit motel, two bed/two bath waterfront condos, or an RV Resort with full hook ups. The Chokoloskee Island Resort is located on the west side of the island, and provides on-site conveniences like a marina launch ramp, boat rental, kayak rental, and more. Staying on Chokoloskee is truly the best jumping off point for anyone looking to get out on the water and explore, fish, and see the surrounding sights.

Where to Fish in and Around Chokoloskee

A bigger question may be—where NOT to fish in Chokoloskee. The fact is, there isn’t a bad place to wet a line around here, as Chokoloskee and the surrounding area is known as some of the best fishing in Florida.

Head north and you’ll find rivers and creeks that serve as excellent fishing spots for redfish, snook, grouper, tarpon, and others. The Pumpkin, Little Wood, Wood, East, Fakahatchee, Ferguson, Barron and Turner rivers all empty into larger bays with islands dotting the area. Within those islands, tidal waters weave through and form passes that house Spanish mackerel and a variety of grouper, depending on the season. At any time, anglers can expect to find snapper, trout, and ladyfish.

In the opposite direction, the south rivers of Lopez, Chatham, Houston, Lostman's, Rodgers, Broad and Harney are formed from backcountry bayous and saltwater bays, housing oyster bars and other marine life.

No matter where you choose to cast your line, you’ll find an abundance of fish to tackle, and beautiful scenery to enjoy in the meantime.

Woman on kayak with cooler and American flag


Kayaking and Guided Eco Tours in Nature

Maybe you’re not an angler, but that doesn’t mean you can’t explore the wildlife around Chokoloskee. Take a kayak or an eco-tour through sheltered mangroves. Discover beaches, exotic scenery and new waterways that help you get the most out of your experience in the Ten Thousand Islands and Chokoloskee. Sightseeing is one of the best ways to experience the history and appreciate the nature of this Paradise Coast gem.

Other Experiences Around Chokoloskee

Just a short distance from Chokoloskee Island are Naples and Marco Island. With many activities and attractions, fine dining, wonderful beaches and other things to explore in these areas, it’s easy to make Chokoloskee part of your Paradise Coast trip.

A quick 34 miles away, Marco Island gives you the ultimate in shopping excursions and dining experiences. Here, the flavors of Paradise can be found in locally caught seafood, and award-winning restaurants.

Wander further north to Naples and you can experience luxury beaches and waterfront resorts on a stunning five-mile stretch of white sand. Starting at the southern part of Naples is a 35-acre public beach preserve, Clam Pass Park. Here, you can take guided tours, walk the boardwalk and trails, or spend some time at the lagoon.

Vanderbilt Beach Park is north of Clam Pass and one of the most popular public beaches in Florida’s Paradise Coast. Further north brings you to Delnor-Wiggins Pass State Park, with 2,000 acres of wild, untamed beach.

Immerse yourself in the nature that surrounds Chokoloskee Island. Venture around the sights and attractions nearby. Embrace your inner angler or explorer. You might find yourself returning again and again.