Key West Cruises, Sailing & Water Tours

31 Results
Key West Classic Day Sail Aboard America 2.0

Sail aboard the fastest and most elegant schooner in Key West, Schooner America 2.0! This boat is a replica of the 1851 Schooner America that …More

Likely to Sell Out
Likely to Sell Out

Sail aboard the fastest and most elegant schooner in Key West, Schooner America 2.0! This boat is a replica of the 1851 Schooner America that...

1 hour 30 minutes • Free Cancellation
5.0 (211)
from
$79
Half-Day Cruise with Kayaking and Snorkeling

This trip combines sailing, snorkeling, kayaking, and local insight in a laid-back, small-group setting. You'll sail on an authentic schooner into the calm, protected waters …More

Likely to Sell Out
Likely to Sell Out

This trip combines sailing, snorkeling, kayaking, and local insight in a laid-back, small-group setting. You'll sail on an authentic schooner into the calm, protected waters...

4 hours 30 minutes • Free Cancellation
4.9 (2,656)
from
$125
Wild Dolphin Sail & Shallow-water Snorkel

Avoid the crowded big boats. Trips on this Sailing Catamaran are 1/2 full maximum! Book with a 2 week cancelation policy from vender, and there’s …More

Likely to Sell Out
Likely to Sell Out

Avoid the crowded big boats. Trips on this Sailing Catamaran are 1/2 full maximum! Book with a 2 week cancelation policy from vender, and there’s...

4 hours
4.8 (438)
from
$109
Reef Snorkel & Sail Adventure – Morning

Join us for a snorkel adventure to the only living coral reef in North America. We have several fantastic reefs to choose from on both …More

Join us for a snorkel adventure to the only living coral reef in North America. We have several fantastic reefs to choose from on both...

3 hours • Free Cancellation
4.9 (239)
from
$79
Small-Group Sunset Sail with Wine

The Wind & Wine Sunset Sail offers a boutique experience unlike any other in Key West! This isn’t your typical party boat—it’s a calm, uncrowded …More

Likely to Sell Out
Likely to Sell Out

The Wind & Wine Sunset Sail offers a boutique experience unlike any other in Key West! This isn’t your typical party boat—it’s a calm, uncrowded...

2 hours • Free Cancellation
5.0 (1,705)
from
$135
Key West Half-Day Fishing Charter

Fish like never before! Our custom build 64' catamaran is perfect for a more stable, relaxing ride. You'll fish for a wide variety of the …More

Likely to Sell Out
Likely to Sell Out

Fish like never before! Our custom build 64' catamaran is perfect for a more stable, relaxing ride. You'll fish for a wide variety of the...

5 hours • Free Cancellation
4.7 (489)
from
$95
Key West Wind & Wine Private Charter

The Wind & Wine Key West Sunset Sail has been honored with a #1 rating on Tours of Key West three years running. See the …More

The Wind & Wine Key West Sunset Sail has been honored with a #1 rating on Tours of Key West three years running. See the...

2 hours (approx.) • Free Cancellation
5.0 (1,705)
from
$3,499
Key West Sunset Cocktail Cruise

“The Key West Cocktail Cruise is the best thing to happen to Sunsets since cameras and sunglasses!” This is not your average Key West pleasure …More

“The Key West Cocktail Cruise is the best thing to happen to Sunsets since cameras and sunglasses!” This is not your average Key West pleasure...

2 hours
4.9 (181)
from
$65
All Inclusive Water Adventure Excursion in Key West

Tours of Key West is the only tour operator in Key West offering sailing excursions on a historic schooner into the remote backcountry of the …More

Likely to Sell Out
Likely to Sell Out

Tours of Key West is the only tour operator in Key West offering sailing excursions on a historic schooner into the remote backcountry of the...

6 hours 30 minutes • Free Cancellation
4.9 (2,656)
from
$159
Looe Key Snorkel

Looe Key Marine Sanctuary is part of the Great Florida Reef, the only coral reef in the continental USA, and the third largest barrier reef …More

5.0 (444)

Looe Key Snorkel

Looe Key Marine Sanctuary is part of the Great Florida Reef, the only coral reef in the continental USA, and the third largest barrier reef...

3 hours • Free Cancellation
5.0 (444)
from
$569
Guided Mangrove Eco Tours Kayak or Paddleboard Adventure

Explore the serene mangrove waterways of Geiger Key on this guided eco-tour. Perfect for all ages and levels of experience. Choose between a single kayak, …More

Explore the serene mangrove waterways of Geiger Key on this guided eco-tour. Perfect for all ages and levels of experience. Choose between a single kayak,...

2 hours • Hotel pickup offered • Free Cancellation
4.9 (24)
from
$75

Frequently Asked Questions

These answers are based on answers previously given to Tours of Key West customers' questions.

Key West Tours