Chokoloskee Island
A National Historic District built on an ancient Calusa shell mound — one of the largest on the Gulf coast — and the small fishing village where the Ten Thousand Islands begin.
Departing Southwest Florida
Boat Tours from Chokoloskee Island, Florida
Chokoloskee Island sits at the wild southern edge of the Ten Thousand Islands, a fishing village built on a centuries-old shell mound where the road simply stops. Our boats don’t launch from Chokoloskee itself — we run the same mangrove wilderness from Goodland and Naples, a scenic drive west, with our own shell bars, dolphins and Gulf sunsets waiting.
Drive timeRoughly 45 minutes to an hour to our docks
Departs fromSan Marco Marina, Goodland, or Naples Bay Resort & Marina
Same wildernessWestern Ten Thousand Islands & Panther Key
Great forHistory buffs, paddlers & Everglades road-trippers
Same Wilderness, Different Dock
Chokoloskee’s wild edge, and our side of it
Chokoloskee is one of Southwest Florida’s most storied spots — a small fishing village built atop an ancient Calusa shell mound at the very end of County Road 29. Ted Smallwood’s century-old trading post still stands on stilts over Chokoloskee Bay, and just up the road, Everglades City anchors the Gulf Coast entrance to Everglades National Park. It’s the kind of place where the pavement runs out and the Ten Thousand Islands simply begin, drawing paddlers, anglers and history buffs from all over.
We don’t run tours out of Chokoloskee or Everglades City — our boats leave from San Marco Marina in Goodland and Naples Bay Resort & Marina in Naples, each roughly 45 minutes to an hour’s drive away along US-41. It’s worth the trip: from our docks you reach the western, Gulf-facing stretch of the very same Ten Thousand Islands wilderness, with easier access to open-water shelling beaches, dolphin-rich passes and the storm-toppled Cape Romano dome ruins.
Think of it as two doors into one wild place. Chokoloskee’s backcountry rivers and mangrove creeks are best explored with the Everglades City outfitters based right there. Our captains specialize in the Gulf side of the same wilderness — barrier keys like Panther Key, remote shell bars refilled by every tide, and the dolphins that work the passes — all a scenic, easy drive from Chokoloskee’s own doorstep.
- Not a Sand Dollar departure point — but a short, scenic drive from one
- Reach the same Ten Thousand Islands wilderness from Goodland & Naples
- Gulf-side shell bars, dolphin passes & the Cape Romano ruins
- Pairs naturally with a Smallwood Store & Everglades City day trip
Pick Your Adventure
Boat tours you can reach from Chokoloskee
None of these depart Chokoloskee directly, but all run the same wild water from our Goodland & Naples docks, a scenic drive away. Tap a tour for full details and live booking.
Shelling ToursHunt rare shells on remote barrier islands the tide just refilled.
Dolphin & WildlifeWild bottlenose dolphins, manatees, ospreys & roseate spoonbills.
Beach & IslandCastaway on a roadless Gulf island for swimming, sandcastles & shells.
Fishing ChartersRelaxed inshore fishing with a local guide — great for first-timers.
Private ChartersThe whole boat is yours — a captain and an itinerary built around you.
The Wider Ten Thousand Islands
Chokoloskee’s wilderness, and the western half we call home
Chokoloskee sits at the historic southern doorway to the Ten Thousand Islands. Our boats run the same wilderness from the Goodland & Naples side, a scenic drive west.
Smallwood Store
Ted Smallwood’s 1906 trading post still stands on stilts over Chokoloskee Bay, now a museum on the old frontier-Everglades way of life.
Everglades City & the Gulf Coast Visitor Center
The gateway town just north of Chokoloskee, home to Everglades National Park’s Gulf Coast entrance and its own ranger-led backcountry tours.
Panther Key
A Ten Thousand Islands key further up the chain toward our docks — part of the same mangrove-and-shell-bar system our Goodland trips explore.
Chokoloskee Bay & the mangrove backcountry
The tea-colored bay and winding creeks that link Chokoloskee to the open Gulf — famously good paddling water at the southern edge of the refuge.
Goodland & San Marco Marina
Our own dock, a scenic drive west — the launch point for the Gulf-side stretch of this same Ten Thousand Islands wilderness.
🗺️ Chokoloskee and our Goodland dock bookend the same Ten Thousand Islands — one via Everglades City outfitters, the other with us.
Find Your Trip
Perfect for a Chokoloskee-area visit
Staying near Chokoloskee or Everglades City? Here’s who makes the drive to our docks.
History & Smallwood Store visitors
Pair a walk through Old Florida history with a Gulf-side boat day at our nearby dock.
Everglades paddlers & backcountry campers
Trade the kayak for a boat and see the western Ten Thousand Islands from open water.
Families road-tripping US-41
Break up the Tamiami Trail drive with shelling, dolphins or a Gulf sunset.
Anglers
Backcountry fishing is close to Chokoloskee — or book an inshore charter from our dock instead.
On the Water Nearby
A few moments from our side of the Ten Thousand Islands
Real guests, real islands, a scenic drive from Chokoloskee. Tap any photo to look closer.
Keep Exploring
More of the coast, and nearby drive-in trips
Whether you’re deciding between our two departures or driving in from another direction, these help.
Ten Thousand Islands Boat ToursThe wild Gulf-side wilderness we run from our Goodland dock.
Boat Tours from Vanderbilt Beach, NaplesNorth Naples’ beach strip, a scenic drive to our dock.
Boat Tours from Olde Naples & Downtown5th Avenue South & Tin City, minutes from the marina.
Boat Tours in North Naples, FloridaMercato & the north end, a short drive to the water.
Boat Tours from East Naples, FloridaThe closest of the bunch to our Goodland dock.
Good to Know
Chokoloskee boat tour questions
Planning a trip from the Chokoloskee or Everglades City area? Here’s what guests ask most.
Do your boat tours leave from Chokoloskee Island?
No — our boats depart from San Marco Marina in Goodland and Naples Bay Resort & Marina in Naples, both a scenic drive west of Chokoloskee. We don’t run trips out of Chokoloskee or Everglades City itself, but our docks reach the same Ten Thousand Islands wilderness.
How far is the drive from Chokoloskee to your docks?
Plan on roughly 45 minutes to an hour, whether you’re headed to our Goodland dock or into downtown Naples. Both routes run along US-41 and Collier Blvd through classic Everglades scenery.
What is there to see at Chokoloskee Island?
Chokoloskee is a small historic fishing village built atop an ancient Calusa shell mound, home to the century-old Smallwood Store trading post and the southern doorway to Everglades National Park’s Ten Thousand Islands backcountry.
Is the water near Chokoloskee the same as where you cruise?
It’s the same Ten Thousand Islands system, yes — Chokoloskee sits at the southern end and our Goodland dock sits toward the western, Gulf-facing side. Places like Panther Key are part of that shared mangrove-and-shell-bar wilderness.
Can we go shelling near Chokoloskee?
The barrier keys and shell bars of the western Ten Thousand Islands, reached from our Goodland dock, offer some of the best shelling on this coast. It’s empty shells only in Collier County — live shells, sand dollars and starfish stay in the water.
Should we book an Everglades City outfitter or Sand Dollar?
Everglades City-based tours typically explore the backcountry rivers and mangrove creeks close to Chokoloskee. We run the Gulf-side stretch of the same wilderness from Goodland and Naples — shelling, dolphins, sunsets and private charters — so it comes down to which side of the islands you want to see.
Reserve Your Seats
Book your Ten Thousand Islands boat tour
Live availability and instant confirmation — pick your date and trip and check out securely through FareHarbor, or call and a local captain will help you plan the drive and the day.
The islands await
Cruise the Ten Thousand Islands from our docks
Chokoloskee anchors the wild southern edge — our boats explore the same mangrove maze, shell bars and dolphin water from Goodland and Naples, a scenic drive away. Book your Ten Thousand Islands boat tour today.