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Key West Cruises, Sailing & Water Tours

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Key West Tours

Reef Snorkel & Sail Adventure – Morning
Likely to Sell Out
Likely to Sell Out
4.9 (228)

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...

3 hours • Free Cancellation
3 hours • Free Cancellation
3 hours • Free Cancellation
4.9 (228)
from
$79
Key West Half-Day Fishing Charter
Likely to Sell Out
Likely to Sell Out
4.8 (457)

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...

5 hours • Free Cancellation
5 hours • Free Cancellation
5 hours • Free Cancellation
4.8 (457)
from
$95
Half-Day Cruise with Kayaking and Snorkeling
Likely to Sell Out
Likely to Sell Out
4.9 (2,622)

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...

4 hours 30 minutes • Free Cancellation
4 hours 30 minutes • Free Cancellation
4 hours 30 minutes • Free Cancellation
4.9 (2,622)
from
$125
Wild Dolphin Sail & Shallow-water Snorkel
Likely to Sell Out
Likely to Sell Out
4.8 (437)

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...

4 hours
4 hours
4 hours
4.8 (437)
from
$108.91
Small-Group Sunset Sail with Wine
Likely to Sell Out
Likely to Sell Out
5.0 (1,689)

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...

2 hours • Free Cancellation
2 hours • Free Cancellation
2 hours • Free Cancellation
5.0 (1,689)
from
$135
Key West Wind & Wine Private Charter
5.0 (1,689)

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...

2 hours (approx.) • Free Cancellation
2 hours (approx.) • Free Cancellation
2 hours (approx.) • Free Cancellation
5.0 (1,689)
Best Rate
$3,499
Key West Sunset Cocktail Cruise
4.9 (175)

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...

2 hours
2 hours
2 hours
4.9 (175)
from
$65
All Inclusive Water Adventure Excursion in Key West
Likely to Sell Out
Likely to Sell Out
4.9 (2,622)

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...

6 hours 30 minutes • Free Cancellation
6 hours 30 minutes • Free Cancellation
6 hours 30 minutes • Free Cancellation
4.9 (2,622)
from
$159
Looe Key Snorkel
5.0 (442)

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
3 hours • Free Cancellation
3 hours • Free Cancellation
5.0 (442)
from
$599
Key West Full-Day Island T’ing Eco-Tour: Sail, Snorkel and Kayak Adventure
Special Offer
Special Offer
4.9 (558)

Key West Full-Day Island T’ing Eco-Tour: Sail, Snorkel and Kayak Adventure

Beautiful Key West is surrounded by sparkling blue waters of the Gulf of Mexico, making kayaking and dolphin watching the perfect way to spend a...

6 hours (approx.)
6 hours (approx.)
6 hours (approx.)
4.9 (558)
$124.95
$119.95
Guided Mangrove Eco Tours Kayak or Paddleboard Adventure
4.9 (20)

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,...

2 hours • Hotel pickup offered • Free Cancellation
2 hours • Hotel pickup offered • Free Cancellation
2 hours • Hotel pickup offered • Free Cancellation
4.9 (20)
from
$75

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Lowest Price Guarantee

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We guarantee the lowest price on all the tours available to book on our site. We'll refund the difference if you find the exact tour cheaper online until 48 hours before your tour starts.

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Locate your Tours of Key West Booking Number and the proof of the lower price you found.

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The following conditions apply to all lowest price guarantee refund requests:

  • The lowest price guarantee is available to any customer who makes a qualifying purchase through our website. The qualifying purchase must be a minimum of US$20 (or equivalent).
  • The lowest price guarantee covers retail and prepaid rates available to the general public. This does not include discounts or promotions you may receive (or be eligible for) from third-party sites or organizations such as AAA or AARP or special offers made as part of a membership program, corporate discount, daily deal, group, or rewards program.
  • Tours of Key West promotions cannot be combined with the lowest price guarantee.
  • If you find a lower retail or prepaid rate for the same tour, offered on the same date, time and priced in the same currency as your original purchase, on any other website between the time you book on Tours of Key West and 48 hours before your trip starts, we will refund the difference.
  • The lowest price guarantee does not apply where a lower overall price is found by breaking down the purchased tour into one or more parts sold separately.
  • Tours of Key West reserves the right to verify the lower price details. Examples of acceptable forms of verification include a web screenshot or a web address.
  • All refund decisions will be made at the sole discretion of Tours of Key West.

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Tours of Key West wants to make your searches as relevant as possible. That's why we offer many ways to help you find the right experiences for you.

On some pages, you can select how to sort the results we display and also use filter options to see only those search results that meet your chosen preferences. You'll see explanations of what those sort options mean when you select them.

If you see a Badge of Excellence label, the award is based on average review ratings, share of bookings with a review, and number of bookings through Tours of Key West over a 12-month period.

The importance of any one factor over any other in a sort order varies, and the balance is constantly being reviewed and adjusted. We're always updating our systems and testing new ways to refine and improve your results to make them as relevant as possible to meet your needs.

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