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Key West Sailing Trips

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Key West Tours

Key West Wind & Wine Sunset Sail
Likely to Sell Out
Likely to Sell Out
5.0 (1,681)

Key West Wind & Wine Sunset Sail

Wind & Wine has been the #1 rated sunset sail on Best In Key West for over a decade. In our opinion, this is the...

2 hours (approx.) • Free Cancellation
2 hours (approx.) • Free Cancellation
2 hours (approx.) • Free Cancellation
5.0 (1,681)
$109
$99
Key West Sail, Snorkel, Kayak with Sunset Option
Likely to Sell Out
Likely to Sell Out
4.9 (2,674)

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 (2,674)
$99
$90
Key West Backcountry Safari
Likely to Sell Out
Likely to Sell Out
4.9 (2,674)

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 (2,674)
$120
$99
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 Wind & Wine Private Charter
5.0 (1,681)

Key West Wind & Wine Private Charter

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

2 hours (approx.) • Free Cancellation
2 hours (approx.) • Free Cancellation
2 hours (approx.) • Free Cancellation
5.0 (1,681)
Best Rate
$3,499

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Key West Original Island Jet Ski Tour
Likely to Sell Out
Likely to Sell Out
4.9 (3,012)

Key West Original Island Jet Ski Tour

Get into some wet & wild watersports excitement on the best Key West jet ski tour around – a 90-minute adventure featuring 28 miles of...

1.5 Hours • Free Cancellation
1.5 Hours • Free Cancellation
1.5 Hours • Free Cancellation
4.9 (3,012)
$169.95
$119.95
Key West Split Fishing Charter
Likely to Sell Out
Likely to Sell Out
4.8 (500)

Key West Split Fishing Charter

On a Key West Split Fishing Charter, you save by dividing the charter cost between several people. Book your Key West split-charter fishing trip now...

4 or 6 hours (approx.) • Free Cancellation
4 or 6 hours (approx.) • Free Cancellation
4 or 6 hours (approx.) • Free Cancellation
4.8 (500)
$350
$200
Key West Deep Sea Fishing Charter
Likely to Sell Out
Likely to Sell Out
4.9 (266)

Key West Deep Sea Fishing Charter

Experience the thrill of a Key West deep sea fishing adventure on a hunt for trophy game fish with your own Key West fishing charter...

4, 6 or 8 hours (approx.) • Free Cancellation
4, 6 or 8 hours (approx.) • Free Cancellation
4, 6 or 8 hours (approx.) • Free Cancellation
4.9 (266)
$1,000
$900
Key West Party Boat Fishing Charter
4.7 (147)

Key West Party Boat Fishing Charter

Our Key West Party Boat Fishing Charter is great for an affordable day on the water with friends and family enjoying the best Key West...

6 hours (approx.) • Free Cancellation
6 hours (approx.) • Free Cancellation
6 hours (approx.) • Free Cancellation
4.7 (147)
Best Rate
$69.69

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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 Best In Key West Booking Number and the proof of the lower price you found.

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If everything checks out, we'll refund you the price difference.

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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.
  • Best In 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 Best In 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.
  • Best In 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 Best In Key West.

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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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