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Best results for

Water Activities in Big Pine Key, FL

Showing 841-864 of 978 results
Powerboat Race Viewing Cruise in Key West

Powerboat Race Viewing Cruise in Key West

Watch the Powerboat Races from a captain-led spot on the water

4.9 • 5.9K reviews
$149/ person
Key West Sunset Sail

Key West Sunset Sail

Sail Key West’s historic waterfront aboard a hand-built 86-foot schooner

4.9 • 3K reviews
$91/ person
Key West Tall Ship Sailing Cruise

Key West Tall Ship Sailing Cruise

Hoist sails and take the wheel aboard a 2-masted schooner

4.9 • 3K reviews
$57/ person
8-Hour Key West Sandbar Charter

8-Hour Key West Sandbar Charter

Build a flexible day of sandbars, mangroves, and island stops

5.0 • 76 reviews
$1,272
Historic Harbor Cruise in Key West

Historic Harbor Cruise in Key West

Cruise Key West’s waterfront with local history narrated by a licensed captain

5.0 • 74 reviews
$1,055
Snorkel Coffins Patch Reef & Swim Valhalla Sandbar

Snorkel Coffins Patch Reef & Swim Valhalla Sandbar

Snorkel Coffins Patch Reef, then swim and relax at Valhalla Sandbar

4.9 • 934 reviews
$120/ person
Private 3.5-Hour Reef Snorkel & Sandbar Swim in Marathon

Private 3.5-Hour Reef Snorkel & Sandbar Swim in Marathon

Private Coffins Patch snorkel plus Valhalla Sandbar swim in 3.5 hours

4.9 • 934 reviews
$2,950& up
Trifecta: Snorkel, Sandbar, Sunset

Trifecta: Snorkel, Sandbar, Sunset

Snorkel the reef, unwind at Valhalla Sandbar, and enjoy a Florida Keys sunset cruise

4.9 • 934 reviews
$160/ person
Snorkel, Sandbar & Sunset Charter in Marathon

Snorkel, Sandbar & Sunset Charter in Marathon

Snorkel the reef, relax at Valhalla Sandbar, then cruise back at sunset

4.9 • 934 reviews
$3,967& up
Private Sandbar & Reef Snorkeling Charter In Marathon

Private Sandbar & Reef Snorkeling Charter In Marathon

Choose reef snorkeling or a Valhalla Sandbar swim on a private 2-hour charter

4.9 • 934 reviews
$5,024
Snorkel & Swim Valhalla Sandbar in Marathon

Snorkel & Swim Valhalla Sandbar in Marathon

Snorkel and relax in shallow water at Valhalla Sandbar on a 2-hour boat trip

4.9 • 934 reviews
$120/ person
Snorkel Sombrero Reef & Sandbar Cruise in Marathon

Snorkel Sombrero Reef & Sandbar Cruise in Marathon

Snorkel Sombrero Reef, then relax at Molasses Key sandbar

4.9 • 934 reviews
$147/ person
Private Sombrero Reef Snorkel Cruise in Marathon

Private Sombrero Reef Snorkel Cruise in Marathon

Private snorkel and sandbar cruise at Sombrero Reef with captain and gear included

4.9 • 934 reviews
$3,562
Holiday Party Sailing Charter Key West

Holiday Party Sailing Charter Key West

Private catamaran celebration with bubbly, wines, and party platters

4.9 • 635 reviews
$1,340
Key West 1.5-Hour Classic Day Sailing Cruise

Key West 1.5-Hour Classic Day Sailing Cruise

Sail Key West on Schooner America 2.0 with complimentary soft drinks

4.9 • 593 reviews
Contact for pricing
Sail Key West on a 2-Hour Champagne Sunset Cruise

Sail Key West on a 2-Hour Champagne Sunset Cruise

Sail into the Key West sunset with drinks and hors d'oeuvres included

4.9 • 593 reviews
$127/ person
Key West Full Moon Sailing Cruise

Key West Full Moon Sailing Cruise

Sail Key West's night waters beneath the full moon aboard a 105-foot schooner

4.9 • 593 reviews
$73/ person
Key West Christmas Brunch Sail

Key West Christmas Brunch Sail

Sail Key West’s waters aboard a 105-foot schooner with Christmas brunch and drinks

4.9 • 593 reviews
$236/ person
Key West Wrecker's Race Sailing Cruise

Key West Wrecker's Race Sailing Cruise

Join Key West schooners in a monthly race to Sand Key Lighthouse

4.9 • 593 reviews
$127/ person
Key West Christmas Day Sunset Sail

Key West Christmas Day Sunset Sail

Sail into Key West sunset views with holiday treats aboard a 105-foot schooner

4.9 • 593 reviews
$150/ person
23' WorldCat Boat Rental in Cudjoe Key

23' WorldCat Boat Rental in Cudjoe Key

Cruise the Keys on a 23-foot dual-hull World Cat for three days or more

5.0 • 58 reviews
$3,405/ boat
Cudjoe Key 24' Center Console Boat Rental
Up to 8

Cudjoe Key 24' Center Console Boat Rental

GPS-guided center console for Keys exploration

5.0 • 58 reviews
$624/ boat
Double Slide Pontoon Boat Rental in Cudjoe Key
Up to 10

Double Slide Pontoon Boat Rental in Cudjoe Key

Cruise at your own pace with double slides and GPS-marked routes

5.0 • 58 reviews
$681/ boat
Reef, Bay & Wreck Fishing Charter in Cudjoe Key

Reef, Bay & Wreck Fishing Charter in Cudjoe Key

Fish reefs, bays, and wrecks from Cudjoe Key with Capt. Craig

4.9 • 189 reviews
$424& up
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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.

Big Pine Key Things To Do
Fishing Charters236Boat Tours145Boat Rentals124Snorkeling100Yacht Charters92
More
  • Sailing78
  • Scuba Diving69
  • Car Rentals55
  • Sunrise and Sunset Tours44
  • Bike Rentals32
  • Private Fishing Charters27
  • Dolphin Watching22
Kayaking Tours20
  • Jet Skiing17
  • Scenic Flights9
  • Ghost and Haunted8
  • Scavenger Hunts8
  • Scooter Rentals8
  • Dinner Cruises7
  • Paddleboarding7
  • Bar and Pub Crawl6
  • Parasailing6
  • Private Boat Charters6
  • Water Skiing6
  • Helicopter Tours5