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Best results for

Water Activities in Chokoloskee, FL

Showing 25-48 of 225 results
3-Day Kayak & Paddleboard Rental in Marco Island

3-Day Kayak & Paddleboard Rental in Marco Island

Paddle and fish from your Marco Island property at your own pace

5.0 • 1.5K reviews
$113& up
Goodland Backwater Fishing Charter

Goodland Backwater Fishing Charter

Fish Goodland backwaters with gear, bait, and licensing included

5.0 • 96 reviews
$610& up
Full-Day Fishing Charter in Goodland

Full-Day Fishing Charter in Goodland

Target Southwest Florida sport fish with gear and bottled water included

5.0 • 147 reviews
$1,060
8-Hour Everglades National Park Fishing Charter

8-Hour Everglades National Park Fishing Charter

Fish the 10,000 Islands’ bays and backcountry waters

5.0 • 92 reviews
$1,166
Keewaydin Island Shelling Cruise with Biologist Guide

Keewaydin Island Shelling Cruise with Biologist Guide

Cruise to Keewaydin Island for guided shelling with a biologist

5.0 • 863 reviews
$116/ person
3-Hour Marco Island Watersports Lesson

3-Hour Marco Island Watersports Lesson

Private 3-hour tubing, wakeboarding, or waterskiing session for up to 6

5.0 • 876 reviews
$700
Marco Island Dolphin Jet Ski Tour

Marco Island Dolphin Jet Ski Tour

Ride through the 10,000 Islands and look for dolphins

4.9 • 1.3K reviews
$299/ waverunner
Private Shelling Charter in Ten Thousand Islands

Private Shelling Charter in Ten Thousand Islands

Private Ten Thousand Islands shelling tour with a Master Naturalist guide

5.0 • 136 reviews
$672& up
Cruise to Naples for Lunch Private Charter

Cruise to Naples for Lunch Private Charter

Cruise up the coast to Naples for lunch and coastal views

5.0 • 409 reviews
$1,288
Fishing & Sightseeing 10,000 Islands 3-Hour Charter

Fishing & Sightseeing 10,000 Islands 3-Hour Charter

Fish and explore mangrove waterways on a flexible private charter

5.0 • 350 reviews
$504/ boat
Sunset Shelling & Dolphin Tour in Goodland

Sunset Shelling & Dolphin Tour in Goodland

Explore remote islands, search for shells, and watch the Gulf sunset on a private cruise

5.0 • 176 reviews
$554
Private Mangrove Fishing Charter in Marco Island

Private Mangrove Fishing Charter in Marco Island

Cast for local fish in Marco Island’s calm mangrove waters

5.0 • 169 reviews
$451
7-Day Kayak & Paddleboard Rentals in Marco Island

7-Day Kayak & Paddleboard Rentals in Marco Island

Paddle, fish, and explore Marco Island waterways on your own schedule

5.0 • 1.5K reviews
$181& up
10,000 Islands Shelling Tour From Goodland

10,000 Islands Shelling Tour From Goodland

Discover shelling beaches with time for sightseeing and wildlife viewing

5.0 • 96 reviews
$477& up
Offshore Fishing Charter From Goodland

Offshore Fishing Charter From Goodland

Target Southwest Florida sport fish with gear and bottled water included

5.0 • 147 reviews
$1,908& up
Everglades City 8-Hour Wreck Fishing Charter

Everglades City 8-Hour Wreck Fishing Charter

Fish Gulf wrecks and reefs for seasonal species on a private charter

5.0 • 92 reviews
$1,166
Sunset Bird Rookery Boat Cruise

Sunset Bird Rookery Boat Cruise

See birds return to Rookery Bay’s rookery at sunset on a guided cruise with a biologist captain

5.0 • 863 reviews
$105/ person
4-Hour Private Shelling Cruise in Ten Thousand Islands

4-Hour Private Shelling Cruise in Ten Thousand Islands

Private 4-hour shelling and barrier-island tour for up to 12

5.0 • 876 reviews
$1,311
Private Ten Thousand Islands Shelling & Dolphin Boat Tour

Private Ten Thousand Islands Shelling & Dolphin Boat Tour

Explore remote island beaches for shells and coastal wildlife

4.9 • 1K reviews
$1,275& up
Ten Thousand Islands Shelling Tour With Master Naturalist

Ten Thousand Islands Shelling Tour With Master Naturalist

Share a guided shelling charter in Ten Thousand Islands with a Master Naturalist Guide

5.0 • 136 reviews
$151/ person
Marco Island 4-Hour Boat Charter

Marco Island 4-Hour Boat Charter

Cruise Marco Island waterways and unwind on barrier islands

5.0 • 409 reviews
$840
10,000 Islands Fishing & Shelling Charter

10,000 Islands Fishing & Shelling Charter

Fish, shell, or do both on a flexible private trip through the 10,000 Islands

5.0 • 350 reviews
$504/ boat
3-Hour Shelling & Inshore Fishing Tour in Goodland

3-Hour Shelling & Inshore Fishing Tour in Goodland

Tailor private beach shelling and inshore fishing to your family

5.0 • 176 reviews
$554
Private 10,000 Islands Fishing Charter from Marco Island

Private 10,000 Islands Fishing Charter from Marco Island

Cast for varied species, with nearshore wreck fishing when weather allows

5.0 • 169 reviews
$663
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Chokoloskee Things To Do
Boat Tours81Fishing Charters68Kayaking Tours25Dolphin Watching22Bike Rentals20
More
  • Jet Skiing14
  • Beach Tours11
  • Ecotours11
  • Sunrise and Sunset Tours10
  • Boat Rentals8
  • Nature and Wildlife8
  • Yacht Charters6

Travel guides for Water Activities

13 Stunning Beaches in Florida With Clear Water You Need to Visit
Best of Florida • 2026

13 Stunning Beaches in Florida With Clear Water You Need to Visit

Clarity is geology, not luck: quartz sand, seagrass filtration, and how close the Gulf Stream runs. Thirteen beaches, and the trade-off each one asks of you.

Do You Need a License to Rent a Boat in Florida? Your Complete Guide
Best of Florida • 2026

Do You Need a License to Rent a Boat in Florida? Your Complete Guide

Florida issues no boating license at all. What the marina checks is a safety education card, and whether you need one comes down to one date: January 1, 1988.

Car Rentals
5
  • Paddleboarding5
  • Private Fishing Charters4
  • Wildlife Safaris4
  • Bird Watching Tours3
  • National Parks3
  • Off-Road Adventures3
  • Photography Tours3
  • Tubing3