CHOKOLOSKEE, FLORIDA

By  Mike Miller   Updated January 9, 2024

Chokoloskee, Florida is an unincorporated small community of about 359 permanent residents in Collier County located about 35 miles east of Naples and Marco Island.

It is a historic island, once isolated but now connected to Everglades City and the entrance to Everglades National Park by a causeway built in 1956. 

Most natives I've known pronounce it "Chuck a luskee" but the times are changing and as new people move in - who knows?

Welcome Sign at Entrance to Chokoloskee, Florida

The watery landscape all around Chokoloskee Island is low lying, with mangrove islands just peeking above the water surface and sometimes disappearing when the wind and lunar tides are high.

Pelicans in Chokoloskee
Flickr/Rey Perezoso

The island is among Florida's Ten Thousand Islands on the Southwest coast of the Gulf of Mexico, and is on the western edge of the Everglades.

The island's height was caused by shell mounds created during those thousands of years by the people who lived there and ate plenty of shell fish.

THE PIONEER ERA OF CHOKOLOSKEE SETTLEMENT

John Weeks and his family were the first white settlers on Chokoloskee.  They came in 1874.  The community grew slowly and by 1897, five families lived on the island.

In that same year, Ted Smallwood came to town and bought most of the land on the island.  He opened a store in 1906 on the south side of the island serving pioneers and Seminoles.

Vintage Smallwood Store Photo State Archives of Florida

His store was the site of the infamous shooting death of Edgar "Bloody" Watson in 1910.  Mr. Watson was a sugar cane and vegetable grower who had a farm on Chatham Key.

The circumstances of his killing are recounted in numerous articles and books, including one referenced at the end of this article.

One of the first sights you will see on your way onto Chokoloskee Island is a large well maintained RV park and resort on your left. 

It is owned and managed by Outdoor Resorts of America, Inc.

Chokoloskee, Florida Outdoor Resorts of America

Some of the RV lots in this park are for sale now and then and they are very popular with the fishing enthusiasts and their families.

The resort has a beautiful swimming pool at its recreation center and full laundry facilities.  It is not hard to visualize living here full time.

There are also other RV parks in Chokoloskee, and many of the permanent residents also live in small RV's or mobile homes.

The Road to Smallwood Store
Flickr/Rey Perezoso

The community of Chokoloskee is today a destination for people who love the laid back life style. 

Most of these folks also love fishing.  This is the right place for all of them.

Chokoloskee Bay
Flickr/Rey Perezoso

THE HISTORIC SMALLWOOD STORE

Ted Smallwood's General Store is a must see for all who visit  Chokoloskee Island.  It is on the U.S. National Register of Historic Places.

The Smallwood store is a step back into the past and a reminder of the tough life our Florida pioneers had in this watery wilderness.

Smallwood Store
Flickr/Ebyabe

The store was established in 1906 and has now become a museum that is open every day.  You will learn about the early Calusa Indians whose shell mounds created the island.

You will see exhibits and archives about the early Miccosukee and Seminole Indians that made Smallwood's their main trading post.

There also books, DVD's, and other objects relating to the history of this remote part of Southwest Florida.  Some of these can be purchased in the museum's gift shop.

PLACES TO EAT ON CHOKOLOSKEE ISLAND

The most popular restaurant in Chokoloskee is the Havana Cafe of the Everglades.  It's menu fittingly includes some delicious seafood entrees as well as many Latin based dishes. 

Havana Cafe of the Everglades

My favorite when I visit is their blackened grouper with rice and beans.  A close second for me is their Cuban sandwich.

There is a beautiful outside dining area fringed by palm trees and bougainvillea.  The restaurant is open 7 days a week from 9am to 4pm.  Read our review here:

Havana Restaurant of the Everglades.

PLACES TO EAT IN NEARBY EVERGLADES CITY

Most of the restaurants if you visit this remote island town are four miles north across the causeway in Everglades City.  Check here for a list of those restaurants along with reviews by customers:  

Chokoloskee and Everglades City Restaurants

FISHING IS A WAY OF LIFE ON CHOKOLOSKEE ISLAND

Fishing is the main passion and pastime on Chokoloskee Island.  Both visitors and permanent residents are here because of the bounty of the surrounding waters.

Chokoloskee Parkway Motel and Marina
Flickr/lucico

There is also a commercial fishing industry and that makes it a sure thing to get fresh seafood for lunch and dinner.

There are also many charter fishing outfits on Chokoloskee that can take you on a trip to catch some fish.  There are also tours that will take you out into the Ten Thousand Islands and the Everglades.

Airboat tours are one of the most popular activities here, and kayak rentals are also available.

Tripadvisor's Best Fishing Charters

PLACES TO STAY ON CHOKOLOSKEE ISLAND

Chokoloskee Island Park and Marina

There are a few motels and inns on Chokoloskee Island and even more in Everglades City.  In addition to these, many people have cottages, homes, and even recreational vehicles available to rent.

A favorite spot for tourists is the Chokoloskee Island Park and Marina.

Chokoloskee Motels and Other Places to Stay

Although fishing is by far the favored activity here, there are some other interesting things to see and do.

THINGS TO DO IN CHOKOLOSKEE, FLORIDA

Smallwood Store
360 Mamie St, Chokoloskee, FL 34138 | (239) 695-2989

Smallwood Store, discussed earlier, is a historic trading post that has been transformed into a museum, preserving the rich history of Chokoloskee and the Everglades.

We enjoy exploring the artifacts and displays that tell stories of the pioneers and Native Americans who lived in the area.

Visitors like the old-fashioned feel of the place, with its original goods and tools still on display. The waterfront location also offers beautiful views of Chokoloskee Bay.

Chokoloskee Bay
Chokoloskee, FL 34138

Chokoloskee Bay is a pristine natural area perfect for fishing, kayaking, and bird watching. We enjoy the peaceful boat rides and the opportunities to see dolphins, manatees, and a variety of bird species.

The bay’s mangrove-lined shores are great for exploring by kayak, offering a closer look at the local flora and fauna. Visitors appreciate the untouched beauty and the chance to escape into nature.

Everglades City Airboat Tours
907 Dupont St, Everglades City, FL 34139 | (239) 695-2400

Everglades City Airboat Tours provide an exhilarating way to explore the nearby mangrove jungles and open waters.

We enjoy the high-speed rides and the informative guides who share fascinating details about the ecosystems and wildlife.

Visitors love the thrill of skimming over the water and the up-close encounters with alligators and other wildlife.

Outdoor Resorts of Chokoloskee
150 Smallwood Dr, Chokoloskee, FL 34138 | (239) 695-2881

Outdoor Resorts of Chokoloskee, discussed earlier on this page, offers a range of amenities and activities for those who enjoy the RV lifestyle or prefer staying in cottages.

We enjoy the waterfront views, swimming pool, and boat docks. The resort is a great base for exploring the surrounding areas by water or land.

Visitors like the comfortable accommodations and the friendly community.

Chokoloskee Island Park and Marina
1150 Hamilton Ln, Chokoloskee, FL 34138 | (239) 695-2414

Chokoloskee Island Park and Marina, neighboring Everglades National Park, is a favorite spot for anglers and boaters.

We enjoy the full-service marina, bait shop, and the easy access to some of the best fishing spots in the area.

The park’s natural beauty and tranquil environment make it a great place for a picnic or a sunset walk. Visitors appreciate the helpful staff and the well-maintained facilities.

Watson’s Place
Everglades National Park, Chokoloskee, FL 34138 |

Watson’s Place is a historical site within the Everglades National Park, known for its intriguing past and beautiful natural setting.

We enjoy hiking to this secluded spot and learning about the mysterious tale of Edgar J. Watson, a pioneer and alleged outlaw.

The area is also great for wildlife viewing and photography. Visitors like the blend of history and nature that this place offers.

Turner River Kayak Launch
41015 US-41, Ochopee, FL 34141

Turner River Kayak Launch in nearby Ochopee provides an excellent starting point for exploring the mangrove tunnels and waterways of the Everglades. We enjoy the peaceful paddling and the stunning scenery along the Turner River.

It’s a fantastic way to observe the diverse wildlife and the unique landscapes of the region. Visitors appreciate the well-maintained launch facilities and the sense of adventure that kayaking here brings.

Smallwood Store Boat Tours
360 Mamie St, Chokoloskee, FL 34138 | (239) 695-0016

Smallwood Store Boat Tours offers guided tours that explore the remote areas of Chokoloskee Bay and the surrounding waters. We enjoy the informative commentary about the history and ecology of the area, as well as the chance to see dolphins, manatees, and numerous bird species.

They offer Eco, Island and Everglades National Park Sunset Tours, among other tours like the historical Bloody Watson day tours. Visitors like the comfortable boats and the knowledgeable captains who ensure a memorable experience.

• Killing Mr. Watson by Peter Matthiessen (Available at Amazon) Edgar Watson was a pioneer who lived on Chatham Island south of Chokoloskee.  He is known to history as Ed "Bloody" Watson.
  
  The book is a best-selling novel published in 1990. Watson had been somewhat of an outlaw in Florida even before arriving in Chokoloskee Bay country.  He was a good farmer, but was suspected by the locals of many killings in the area. 
  
  One day in 1910 a large crowd of armed citizens assembled at Smallwood's Store and riddled him with bullets when he came to the store by boat.
  
  
• Totch, A Life in the Everglades by Loren "Totch" Brown (Available at Amazon).  He was an authentic Florida Cracker whose family roots went back in the area for generations.
  
  He lived off the land, especially his beloved Everglades and the Ten Thousand Islands.  This book is his autobiography and will make you wish he had written more because he had a gift for describing the hard times he endured and the land he loved.
  
  
• The Story of the Chokoloskee Bay Country: With the Reminiscences of Pioneer C.S. "Ted" Smallwood by Charlton W. Tebeau.  (University of Miami Press, Coral Gables).
  
  Mr. Tebeau was a professional historian and this book is his account of what he learned from some of the area pioneers.  Ted Smallwood, Charles G. McKinney. Rob Storter and many other pioneers were interviewed by Mr. Tibeau. 
  
  This book is an excellent look at a pioneer era in a hard land.