Top Key West Water Sports

70 Results
Marathon Snorkeling and Sandbar Adventure

Discover the best of the Florida Keys with a thrilling snorkeling and sandbar adventure from Marathon Mermaid. Begin at the stunning Sombrero Reef, where vibrant …More

Likely to Sell Out
Likely to Sell Out

Discover the best of the Florida Keys with a thrilling snorkeling and sandbar adventure from Marathon Mermaid. Begin at the stunning Sombrero Reef, where vibrant...

4 hours Free Cancellation
4.8 (5)
from
$129
Dolphin Watching Key West and Snorkeling

This isn’t a packed tourist boat — it’s a true small-group adventure with a maximum of 6 guests. You’re not watching dolphins from far away; …More

This isn’t a packed tourist boat — it’s a true small-group adventure with a maximum of 6 guests. You’re not watching dolphins from far away;...

3 hours Free Cancellation
4.9 (49)
from
$149
Biologist Owned & Operated: Dolphin Watching & Guided Snorkeling

Introducing Squid! The quietest experience you will have on a boat while watching dolphins. We worked with David Walworth, an MIT educated Naval Architect and …More

Introducing Squid! The quietest experience you will have on a boat while watching dolphins. We worked with David Walworth, an MIT educated Naval Architect and...

4 hours Free Cancellation
4.9 (576)
from
$150
Key West: Sunset Sail + Reef Snorkel & Sandbar

Reef Snorkel + Sandbar & Sunset Sail • Summer Only with Small Groups on an Honest Eco Tour. What Makes this Eco Tour different? • …More

Likely to Sell Out
Likely to Sell Out

Reef Snorkel + Sandbar & Sunset Sail • Summer Only with Small Groups on an Honest Eco Tour. What Makes this Eco Tour different? •...

4 hours 30 minutes Free Cancellation
5.0 (56)
from
$150
Key West SNUBA Experience

Go Beyond Snorkeling is the closest you can get to scuba diving without being Dive Certified! Go Beyond Snorkeling into new depths for greater durations where you …More

Go Beyond Snorkeling is the closest you can get to scuba diving without being Dive Certified! Go Beyond Snorkeling into new depths for greater durations where you...

3 hours 30 minutes
5.0 (499)
from
$160
Key West Sandbar Charter With Kayak Tour: Includes Lunch & Drinks

Join us for the ultimate sandbar adventure in Key West. This trip combines the best activities Key West has to offer. We will cruise out …More

Join us for the ultimate sandbar adventure in Key West. This trip combines the best activities Key West has to offer. We will cruise out...

5 hours Free Cancellation
4.9 (425)
from
$161
Key West Hidden Sanctuary Mangrove Kayak Tour With Drinks

Key West’s Most Secluded Kayak & Sandbar Adventure Escape the crowds and explore Key West’s most secluded kayak tour in the Florida Marine Sanctuary. Unlike …More

Key West’s Most Secluded Kayak & Sandbar Adventure Escape the crowds and explore Key West’s most secluded kayak tour in the Florida Marine Sanctuary. Unlike...

5 hours Free Cancellation
4.6 (9)
from
$161
Key West Original Full-Day Watersports Adventure

This Key West experience lets you enjoy all that the island has to offer. Sail on a sleek catamaran along the smooth waters of the …More

Special Offer
Special Offer

This Key West experience lets you enjoy all that the island has to offer. Sail on a sleek catamaran along the smooth waters of the...

6 hours (approx.) Free Cancellation
4.9 (739)
$200
$169
Key West Safari Eco Sandbar Tour Adventure with Snorkeling

Explore Key West in a fun and unique way! Avoid the crowds on this exciting snorkel safari adventure and captain your own speedboat through 28 …More

Explore Key West in a fun and unique way! Avoid the crowds on this exciting snorkel safari adventure and captain your own speedboat through 28...

2 hours 30 minutes Free Cancellation
4.7 (220)
from
$197
Half Day Luxury Boat Tour in Key West with Snorkeling

Enjoy the Thrill of the open sea and the comfort of top class amenities, ideal for sunbathing, sightseeing or simply relaxing with your group exploring …More

Enjoy the Thrill of the open sea and the comfort of top class amenities, ideal for sunbathing, sightseeing or simply relaxing with your group exploring...

4 hours Free Cancellation
5.0 (3)
from
$200
Key West Scuba Diving Refresher Course & Dive

The Cool Shore Excursions Scuba Refresher course is a safe, fun skills review perfect for Open Water divers who have been out of the water …More

Special Offer
Special Offer

The Cool Shore Excursions Scuba Refresher course is a safe, fun skills review perfect for Open Water divers who have been out of the water...

8 hours (approx.) Free Cancellation
5.0 (22)
$229
$225
Key West PADI® Discover Scuba 1-day Resort Course

The is the absolute best way for a person to experience diving. Great for those who want to try scuba diving in Key West. …More

Likely to Sell Out
Likely to Sell Out

The is the absolute best way for a person to experience diving. Great for those who want to try scuba diving in Key West....

9 hours (approx.) Free Cancellation
4.9 (146)
$269
$229
Dry Tortugas National Park Day Trip by Luxury Private Boat

Experience the Dry Tortugas in Unrivaled Luxury and Style aboard the Axopar 37 XC. This exclusive day trip offers the thrill of a high-performance luxury …More

Experience the Dry Tortugas in Unrivaled Luxury and Style aboard the Axopar 37 XC. This exclusive day trip offers the thrill of a high-performance luxury...

8 hours Free Cancellation
4.9 (10)
from
$250
Tropical Drift - A Key West Sunset Cruise

Private 2-Hour Key West Sunset Cruise | Luxury Manitou Pontoon | Up to 10 Guests Leave the crowds behind and experience the magic of a …More

Likely to Sell Out
Likely to Sell Out

Private 2-Hour Key West Sunset Cruise | Luxury Manitou Pontoon | Up to 10 Guests Leave the crowds behind and experience the magic of a...

2 hours Free Cancellation
from
$350
PRIVATE Guided Mangrove Eco-Tour Adventure

Paddle through the serene waters of Geiger Key at your own pace, with a private guided kayak/Paddleboard tour that immerses you in the natural beauty …More

Paddle through the serene waters of Geiger Key at your own pace, with a private guided kayak/Paddleboard tour that immerses you in the natural beauty...

2 hours Hotel pickup offered Free Cancellation
5.0 (2)
from
$395
Key West PADI® Open Water Scuba Certification

Before Looking for a Great Adventure in Key West? Enter the amazing world of scuba diving the fun and easy way with PADI® Open Water …More

Before Looking for a Great Adventure in Key West? Enter the amazing world of scuba diving the fun and easy way with PADI® Open Water...

2 days (approx.) Free Cancellation
5.0 (15)
from
$499
Private Key West Sandbar and Paddle by Boat

Enjoy a private half day adventure for up to 6 guests aboard our late model pontoon boat. Guests may discover and observe diverse marine habitats …More

Enjoy a private half day adventure for up to 6 guests aboard our late model pontoon boat. Guests may discover and observe diverse marine habitats...

3 hours 30 minutes Free Cancellation
5.0 (38)
from
$600
Key West PADI® Advanced Open Water Diver Scuba Certification

Go deeper into the world of Scuba with PADI® Advanced Open Water Diver certification. Expand your skills and experience, qualify for pro-level dive training. …More

Special Offer
Special Offer

Go deeper into the world of Scuba with PADI® Advanced Open Water Diver certification. Expand your skills and experience, qualify for pro-level dive training....

2 days (approx.) Free Cancellation
5.0 (2)
$699
$659
Sandbar Excursions with Snorkeling and Sunset Cruises in Key West

Explore the beautiful waters of Key West with us, where the adventure includes snorkeling in crystal blue waters, lounging on secluded beaches, and witnessing stunning …More

Likely to Sell Out
Likely to Sell Out

Explore the beautiful waters of Key West with us, where the adventure includes snorkeling in crystal blue waters, lounging on secluded beaches, and witnessing stunning...

4 hours Free Cancellation
5.0 (4)
from
$700
Pontoon Boat Rental with Slides from Key West

Double Decker Pontoon Boat with slides for up to 14 passenger Rental in sunny Key West, Florida. Want a stress-free day? Hire a captain and …More

Double Decker Pontoon Boat with slides for up to 14 passenger Rental in sunny Key West, Florida. Want a stress-free day? Hire a captain and...

4 to 8 hours Free Cancellation
from
$806

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These answers are based on answers previously given to Cool Shore Excursions customers' questions.

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