Florida Travel Blog - Destinations in Florida

Florida Travel Blog 

Travel destinations, beaches and attractions and things to do in Florida. Documented by RESIDENTS of Florida.

Chokoloskee Florida – Big History, Little Island in the Everglades

The Little Everglades Island With a BIG History!

Where is Chokoloskee, Florida

There is a little island at the end of a road in the Everglades that has more historical significance than some major cities! Chokoloskee, Florida is a ¼-mile square patch of land bordering the Everglades to the north and east, and the Ten Thousand Islands on the west and south.

The island is just over a small bridge from Everglades city – see the map of Chokoloskee.

Most of the island is slightly above sea level due to the mounds of shells from hundreds of years of Indian occupation.

Chokoloskee is right in the middle of the Everglades. The best part of the Everglades.

Today, the 400 or so inhabitants are involved in the fishing business. Some as charter captains, others as commercial fishermen, and many more run various support businesses like motels, small resorts and campgrounds. Basically, you could say Chokoloskee, Florida is the classic definition of a sleepy little fishing village.

Chokoloskee Florida History

Beginning in the late 1800s, the native Indians were gone, killed or forced out, and settlers took their place. The area was fertile and full of fish and oysters.

On the mainland were deer, various birds, raccoons and other meat sources. Chokoloskee became a trading center of some repute. Locally grown tomatoes, cane syrup and fish were traded for needed supplies.

Regular traveling trader boats traveled between Chokoloskee and Key West. Most news from the outside world came from the sailors on board these vessels.

History has another view of Chokoloskee and the surrounding bay – and it’s not so sleepy! The area was extremely remote.

Chokoloskee Florida Gets Contact with the Mainland

The causeway existing today wasn’t built until 1956. You could only reach the island by water, which was perfect for some notorious individuals avoiding the law.

There are numerous books written about various Everglades outlaws, none more documented than Edgar J. Watson.

Watson was an alleged serial killer. He even was charged by locals saying he shot Belle Starr, the one-time girlfriend of Jesse James and/or Cole Younger during their outlaw days.

things you need when flying

Watson was never convicted, despite evidence to the contrary. He lived along the banks of Chokoloskee Bay by farming. Legend has it that his farm hands would disappear when it was time for payday. Bodies were never found, but there were a lot of fat alligators around.

Among the criminal mischief surrounding the area, nothing was more prolific than moonshine. It has been reported that few shipments of vegetables left the island without some “low bush lightning” being sheltered by stacks of vegetables.

The moonshine would end up in Key West.  Prior to the end of prohibition, the swamps were filled with the smell of “shine”.

Notable scoundrels roaming the area were plume hunters. The price for feathers from birds in the area was about the same as gold! Hat makers in New York paid handsomely for the bright feathers of egrets, herons, ibises and spoonbills in the Everglades.

By the early 1900s conservationists realized the bird populations were being decimated. However, it wasn’t until after several game wardens were shot trying to make arrests that the public outcry stopped the plume hunting.

Smallwood Store Comes to Chokoloskee

Noting the importance of Chokoloskee as a trading area, Ted Smallwood opened a trading post in 1906 on the south end of the island. People from all around the area came for everything from basic food supplies, to mail and other goods from Key West.

It was a common sight to see Seminole Indians, local fishermen, farmers, and hunters congregating at the Smallwood store in skiffs, dugout canoes small schooners and rowboats.

The Smallwood Store, after several hurricane remodels, still stands today as a museum and tribute to Ted Smallwood. Visit the store and museum most days from 10 AM to 5 PM.

Like most things in this laid-back atmosphere, you may want to call to make sure they didn’t go fishing that day! This is old Florida and there are not too many priorities that are more important than a good day of fishing!


Don't bet on everything being open year round except for fishing.
Photo of Chokoloskee Island Park and Marina
Map of Chokoloskee Florida near Everglades city
There is only one way on and off the island without a boat.
choko 4
Fishing is a way of life in this area. Exceptional inshore opportunities for snook, redfish, trout, sheepshead cobia and many more.
choko 6
The legend of Edgar J. Watson continues to grow over the years. They say the home below was on Chokoloskee Bay was where he disposed of his farm hands.

Map of Chokoloskee

Ted Smallwood Store in Chokoloskee Florida
Seminole Indians traded at this Smallwood Store in Chokoloskee Florida
Prior to the caueway, Ted Smallwood's Store was only accessible by water. Traders, farmers, indians, moonshiners and all visited by boat.

Hotels in Chokoloskee

As you would expect on a very small island, there are only a couple of hotels on the Island.

The Parkway Motel and Marina is along the waterfront where fishermen stay in Chokoloskee.

The other notable places to stay in Chokoloskee Florida are actually in Everglades City back across the bridge. The Ivey House and Captain’s Table are the most notable hotels in Chokoloskee that are over the bridge in Everglades City, 3 miles away.

Florida Travel Blog highly recommends you contact the hotel directly. Do not use the booking services like hotels.com and Travelocity. They mislead you on locations and hotel accommodations.

Fishing in Chokoloskee

It should be noted the Chokoloskee Bay area has some of the best inshore fishing in the world. Redfish, snook, trout and many other species are readily available.

Charter Captains dot the island. Many fish both inshore and offshore. Always determine the type of fishing you want to do and confirm with your charter that is what they will be doing.

Take some insect repellent fishing – the “Swamp Angels” are pretty heavy at certain times of the year!

Remember You ARE in the Everglades of Florida

While the Florida Everglades are a naturalist’s dream, aimlessly wandering through the major roads won’t give you any insight into this important ecosystem. Going unprepared may mean an unpleasant experience.

We recommend you;

  • Plan ahead. Know the things you want to see and do. Pick the level you want to delve into this fun wilderness.
  • Bring Sunscreen. The Florida sun can be intense and brutal for light skin even in the winter months.
  • Buy good quality insect repellent. There are various types of insects in the Everglades beyond mosquitoes. Many are species only found here, but they still want to bite!
  • Bring Water. Yes, there are places where potable water is available unless the rainy season or other inclement weather limits access.
  • Wear suitable clothing. If your plans involve walking into the swamps and wetlands, fishing, or hiking, dress appropriately. Long sleeves and long pants may be wise in some areas. Some people even wear mosquito-repellent-covered hats.
  • Keep a camera ready. The best pictures and videos that come out of the Everglades are those that were unplanned and spontaneous. Memories are made here.
  • Stay safety-minded. The Everglades are astonishing, but it’s not Disney World. There are things that want to sting you, bite you and eat you. Stay alert and aware of your surroundings.

Finally, we recommend you do not travel across the Everglades at night. No, we aren’t worried about you, but there is more wildlife killed during the night by car when neither you nor the animal can see.

Directions to Chokoloskee Florida

While it may seem complicated, it is relatively easy to get to Chokoloskee, Florida. The easiest way is to find Everglades City and follow the directions to Chokoloskee.

Specifically, take Rt. 41, the Tamiami Trail, from Naples. As you go east about 30 miles you will see Rt.29 south to Everglades City. Take the road and as you come into Everglades City you will see the sign for Plantation Island and Chokoloskee Island. It will be called Smallwood Road.

Visit Chokoloskee Florida Soon!

The little island of Chokoloskee Florida has big history in the Everglades.

For More About the Everglades

A Captivating Journey Through the Everglades

More Destinations from Florida Travel Blog

Cruise Critic See the world for less Start saving your ideas
Florida Travel Blog
Join our Mailing list!

Get all our latest posts and our monthly Florida Travel Newsletter with the latest posts and Florida Travel News.