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Best results for

Water Activities in Chokoloskee, FL

Showing 73-96 of 225 results
5-Day Kayak & Paddleboard Rental Marco Island

5-Day Kayak & Paddleboard Rental Marco Island

Paddle and fish from your property on your own schedule

5.0 • 1.5K reviews
$158& up
Marco Island Paddleboard Rental

Marco Island Paddleboard Rental

Beginner-friendly inflatable paddleboard rentals with life vests included

4.8 • 110 reviews
$45/ paddleboard
Marco Island 6-Hour Offshore Fishing Charter

Marco Island 6-Hour Offshore Fishing Charter

Fish federally permitted Gulf waters aboard your choice of private offshore boat

4.8 • 102 reviews
$1,563& up
Everglades City Wreck Fishing Charter

Everglades City Wreck Fishing Charter

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

5.0 • 92 reviews
$947
Explore Everglades National Park by Boat & Kayak

Explore Everglades National Park by Boat & Kayak

Reach remote Everglades National Park areas by boat, then kayak and walk with your guide

4.9 • 145 reviews
$220/ person
Offshore Fishing Charter in Marco Island

Offshore Fishing Charter in Marco Island

Fish reefs and wrecks off Marco Island with 4–8 hour charter options

4.9 • 29 reviews
$795& up
Private Ten Thousand Islands Beach Day Cruise from Naples

Private Ten Thousand Islands Beach Day Cruise from Naples

Cruise mangroves to a boat-access-only beach for shelling, exploring, or relaxing

5.0 • 41 reviews
$819
Self-Guided Jet Ski Rental to Keewaydin Island in Naples

Self-Guided Jet Ski Rental to Keewaydin Island in Naples

Ride 35+ miles of Southwest Florida waterways at your own pace

4.9 • 204 reviews
$236/ jet ski
Mangrove & Grassland Airboat Tour in Everglades City

Mangrove & Grassland Airboat Tour in Everglades City

Airboat through mangroves and grasslands with Everglades insight

4.7 • 4.8K reviews
$111/ person
Full-Day Backwater Fishing Charter in Marco Island

Full-Day Backwater Fishing Charter in Marco Island

Light-Tackle Backwater Fishing for Marco Island Species

5.0 • 33 reviews
$1,166
Family Fishing Charter in Naples

Family Fishing Charter in Naples

Cast for seasonal inshore fish with hands-on guidance

5.0 • 27 reviews
$689
Manatee & Dolphin 10,000 Islands Sunset Cruise

Manatee & Dolphin 10,000 Islands Sunset Cruise

Experience a sunset cruise with chances to spot manatees, dolphins, and wildlife in the Everglades.

4.7 • 1.7K reviews
$146/ person
Marco Island Wildlife & Shelling Cruise

Marco Island Wildlife & Shelling Cruise

Island ecology, beachcombing, and kid-friendly boating

5.0 • 1.5K reviews
$21/ person
Kids Paddleboard Rental in Marco Island

Kids Paddleboard Rental in Marco Island

A stable, lightweight inflatable paddleboard rental made for young beginners

4.8 • 110 reviews
$34/ paddleboard
Private Full-Day Offshore Fishing Charter from Marco Island

Private Full-Day Offshore Fishing Charter from Marco Island

Fish offshore wrecks and reefs from a federally permitted private boat

4.8 • 102 reviews
$2,084& up
1.5-Hour Ten Thousand Islands Guided Cruise

1.5-Hour Ten Thousand Islands Guided Cruise

Cruise Ten Thousand Islands mangroves while learning about wildlife and local history

4.7 • 503 reviews
$48/ person
Explore Ten Thousand Islands Shelling Cruise From Marco Island

Explore Ten Thousand Islands Shelling Cruise From Marco Island

Cruise the Ten Thousand Islands Wildlife Refuge and shell remote beaches

4.9 • 145 reviews
$166/ person
Ten Thousand Islands Inshore & Backwater Fishing Charter

Ten Thousand Islands Inshore & Backwater Fishing Charter

Fish the Ten Thousand Islands on a 2–8 hour inshore and backwater charter

4.9 • 29 reviews
$398& up
Ten Thousand Islands Pirate History Cruise

Ten Thousand Islands Pirate History Cruise

Trace pirate lore and Everglades history from secluded island beaches

5.0 • 41 reviews
$382
Naples & Marco Island Kayak Rental

Naples & Marco Island Kayak Rental

Paddle mangrove trails, secluded beaches, and island waterways at your own pace

4.9 • 204 reviews
$48/ kayak
Mangrove Tunnel Airboat & Boat Tour in Everglades City

Mangrove Tunnel Airboat & Boat Tour in Everglades City

Pair a mangrove airboat ride with a Ten Thousand Islands pontoon cruise

4.7 • 4.8K reviews
$121/ person
6-Hour Backwater Fishing Charter From Marco Island

6-Hour Backwater Fishing Charter From Marco Island

Light-tackle backwater fishing with a local Marco Island captain

5.0 • 33 reviews
$875
Family Fishing Charter in Naples

Family Fishing Charter in Naples

Cast for seasonal inshore fish with family-friendly guidance

5.0 • 27 reviews
$477
Private Manatee & Dolphin Sunset Cruise in Naples

Private Manatee & Dolphin Sunset Cruise in Naples

Reserve a private 3-hour sunset cruise for up to 6 passengers

4.7 • 1.7K reviews
$370
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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