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Kid-Friendly Key West Cruises, Sailing & Water Tours

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Key West Tours

Miami to Key West Day Trip with Glass Bottom Boat Cruise
Likely to Sell Out
Likely to Sell Out
4.6 (3,216)

Miami to Key West Day Trip with Glass Bottom Boat Cruise

Sightsee along the famous Overseas Highway then take a Key West Glass-Bottom Boat Cruise when you tour Key West on this great Miami to Key...

6 hours in Key West (approx.) • Hotel pickup offered • Free Cancellation
6 hours in Key West (approx.) • Hotel pickup offered • Free Cancellation
6 hours in Key West (approx.) • Hotel pickup offered • Free Cancellation
4.6 (3,216)
$159
$119
Key West Sail, Snorkel, Kayak with Sunset Option
Likely to Sell Out
Likely to Sell Out
4.9 (2,687)

Key West Sail, Snorkel, Kayak with Sunset Option

Enjoy an unforgettable morning or afternoon of sailing, kayaking and snorkeling in the pristine marine wilderness of the Key West National Wildlife Refuge....

4.5 or 6.5 hours (approx.) • Free Cancellation
4.5 or 6.5 hours (approx.) • Free Cancellation
4.5 or 6.5 hours (approx.) • Free Cancellation
4.9 (2,687)
$99
$90
Key West Backcountry Safari
Likely to Sell Out
Likely to Sell Out
4.9 (2,687)

Key West Backcountry Safari

Spend an unforgettable day sailing emerald waters, kayaking mangrove-shaded channels and snorkeling coral gardens in an unspoiled marine wilderness....

4.5 or 6.5 hours (approx.) • Free Cancellation
4.5 or 6.5 hours (approx.) • Free Cancellation
4.5 or 6.5 hours (approx.) • Free Cancellation
4.9 (2,687)
$120
$99
Key West Sunset Dinner Cruise
Likely to Sell Out
Likely to Sell Out
4.4 (1,864)

Key West Sunset Dinner Cruise

Join us for Key West's Best Sunset Dinner Cruise. This 2 Hour trip Includes an amazing tropical food buffet, live music and open well bar....

2 hours • Free Cancellation
2 hours • Free Cancellation
2 hours • Free Cancellation
4.4 (1,864)
from
$92.95
Key West Sunset Sail with Champagne, Hors D’oeuvres and Full Bar
4.8 (3,733)

Key West Sunset Sail with Champagne, Hors D’oeuvres and Full Bar

Admire an exquisitely painted sky during this premium sunset cruise in Key West. Create fantastic memories as you set sail on a modern sailing catamaran...

2 hours (approx.) • Free Cancellation
2 hours (approx.) • Free Cancellation
2 hours (approx.) • Free Cancellation
4.8 (3,733)
Best Rate
$79.95
Sunset Sip & Sail
Likely to Sell Out
Likely to Sell Out
4.7 (399)

Sunset Sip & Sail

Sunset Sip & Sail: Come see the legendary Key West Sunset on a Brand New Catamaran Sail Boat. • Open bar • Live Music •...

2 hours • Free Cancellation
2 hours • Free Cancellation
2 hours • Free Cancellation
4.7 (399)
from
$72
Key West Sunset Harbor Cruise
Special Offer
Special Offer
4.9 (128)

Key West Sunset Harbor Cruise

Looking for the perfect way to end your day? Join us aboard a 45ft Corinthian powercat, and ride in comfort with this relaxing, catered cruise...

2 hours (approx.) • Hotel pickup offered • Free Cancellation
2 hours (approx.) • Hotel pickup offered • Free Cancellation
2 hours (approx.) • Hotel pickup offered • Free Cancellation
4.9 (128)
$99
$89
Key West Dolphin Watch Sunset Snorkel Cruise
Likely to Sell Out
Likely to Sell Out
4.7 (334)

Key West Dolphin Watch Sunset Snorkel Cruise

The Tours of Key West Dolphin watch triple combo is the best way to watch Dolphins, Snorkel the Key West tropical waters, and see the...

3 hours • Free Cancellation
3 hours • Free Cancellation
3 hours • Free Cancellation
4.7 (334)
from
$69.95
Key West Sunset Sail Aboard Schooner America 2.0
Likely to Sell Out
Likely to Sell Out
4.9 (1,701)

Key West Sunset Sail Aboard Schooner America 2.0

Enjoy an exquisite 2-hour sunset sailing adventure aboard a stunning modern-built schooner! Take in the sights aboard Schooner America 2.0, the most elegant schooner in Key...

2 hours • Free Cancellation
2 hours • Free Cancellation
2 hours • Free Cancellation
4.9 (1,701)
from
$122.59
Key West Sunset Snorkel Sail
Likely to Sell Out
Likely to Sell Out
4.8 (189)

Key West Sunset Snorkel Sail

Enjoy this 3 hour sunset combo trip. We will cruise out to Key West’s best reef location, where you are welcome to jump in and...

3 hours • Free Cancellation
3 hours • Free Cancellation
3 hours • Free Cancellation
4.8 (189)
from
$69.95
Key West Shark and Wildlife Catamaran Tour
Likely to Sell Out
Likely to Sell Out
5.0 (3,229)

Key West Shark and Wildlife Catamaran Tour

This is the only shark tour in the USA and to our knowledge the only tour where guests do not get in the water to...

2 hours • Free Cancellation
2 hours • Free Cancellation
2 hours • Free Cancellation
5.0 (3,229)
from
$99
Key West Schooner Appledore Backcountry Eco-Tour: Sail, Snorkel & Kayak
4.9 (216)

Key West Schooner Appledore Backcountry Eco-Tour: Sail, Snorkel & Kayak

Set sail from Historic Seaport on the Key West Schooner Backcountry Eco-Tour adventure!...

5 hours (approx.) • Free Cancellation
5 hours (approx.) • Free Cancellation
5 hours (approx.) • Free Cancellation
4.9 (216)
Best Rate
$109.95
Key West Dolphin Watch & Snorkel
4.9 (25)

Key West Dolphin Watch & Snorkel

Board the Dolphin Watch & Snorkel Cruise Key West for a journey to observe the beauty of Key West dolphins....

3 hours 30 minutes (approx.) • Hotel pickup offered • Free Cancellation
3 hours 30 minutes (approx.) • Hotel pickup offered • Free Cancellation
3 hours 30 minutes (approx.) • Hotel pickup offered • Free Cancellation
4.9 (25)
Best Rate
$99
Key West Classic Day Sail Aboard America 2.0
Likely to Sell Out
Likely to Sell Out
5.0 (210)

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...

1 hour 30 minutes • Free Cancellation
1 hour 30 minutes • Free Cancellation
1 hour 30 minutes • Free Cancellation
5.0 (210)
from
$79.45
Key West Half-Day Fishing Charter
Likely to Sell Out
Likely to Sell Out
4.8 (451)

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 (451)
from
$95
Half-Day Cruise with Kayaking and Snorkeling
Likely to Sell Out
Likely to Sell Out
4.9 (2,615)

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 (2,615)
from
$125
All Inclusive Water Adventure Excursion in Key West
Likely to Sell Out
Likely to Sell Out
4.9 (2,615)

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 (2,615)
from
$159

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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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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.

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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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