Sailing in Key West delivers reliable, no-nonsense opportunities to experience the Florida Keys from the water. The most worthwhile excursions include sunset catamaran cruises (perfect for photos and included drinks) and morning reef-snorkeling trips that get you up close with tropical fish. While party boats can be fun, I particularly recommend the intimate private charters — they’re pricier but offer unmatched flexibility and local expertise from seasoned captains. For travelers seeking the best value and experience, check our tested recommendations below.
Key Points
- Sunset cruises aboard a 69-foot catamaran with complimentary drinks and an intimate atmosphere, ideal for special occasions.
- Highly-rated sailing and snorkeling adventures with personalized attention, opportunities to spot marine life, and snorkeling equipment provided.
- Party cruises on a 65-foot catamaran with complimentary drinks, appetizers, and live music for a vibrant atmosphere.
- Private and luxury charters with knowledgeable captains, complimentary sparkling wine, and personalized sailing experiences.
- Unique dining and relaxation experiences with sunset sailing, wine tastings, and an exclusive setting for couples and friends.
Champagne Sunset Catamaran Cruise in Key West With Cocktails!
Embarking on a two-hour sunset cruise aboard a 69-foot catamaran, travelers can indulge in a champagne-fueled adventure while taking in the stunning scenery of Key West.
With a 92% traveler recommendation based on over 570 reviews, this excursion offers the perfect mix of relaxation and sightseeing. Guests can sip on complimentary beer, wine, champagne, or sangria as they view marine life and island landscapes, while the captain shares the best spots to witness the sunset.
Boasting a maximum of 86 passengers, this cruise provides an intimate and enjoyable atmosphere, making it an ideal choice for special occasions or simply a relaxing experience.
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Key West: Sunset Sailing Trip With Open Bar, Food and Music
What better way to cap off a day in Key West than with a sunset sailing excursion offering an open bar, tasty appetizers, and live music?
For $69.95, you can embark on a 2-hour journey aboard the Sandie Cat catamaran, departing from the historic Key West seaport.
The cruise accommodates up to 149 passengers, providing ample space to enjoy unlimited rum runners, Champagne, and other drinks while savoring a selection of appetizers.
You’ll even have the chance to assist with raising the sails and snapping photos at the helm.
With an impressive 4.5/5 rating from over 200 reviews, this is a must-do sunset experience in Key West.
Read our full review: Key West: Sunset Sailing Trip With Open Bar, Food and Music Review
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Key West Sailing & Snorkeling: A Reef Adventure
For those seeking a unique blend of sailing and snorkeling adventure in Key West, the Key West Sailing & Snorkeling: A Reef Adventure offers an exhilarating experience.
This highly-rated tour, with a 94% recommendation from travelers, takes participants on a journey to explore the vibrant coral reefs.
With a maximum of 24 travelers, guests can enjoy personalized attention from the crew, who are praised for their professionalism and knowledge.
The tour includes top-notch amenities such as snorkeling equipment, alcoholic and non-alcoholic beverages, and snacks.
While visibility can be mixed, the opportunity to spot sea turtles, sharks, and dolphins makes this a must-try activity for nature enthusiasts visiting Key West.
Read our full review: Key West Sailing & Snorkeling: A Reef Adventure Review
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Key West: Sunset Party Cruise by Catamaran
On the sails of the 65-foot catamaran Fury’s Commotion on the Ocean, travelers can experience a vibrant sunset party cruise in Key West.
The 2-hour excursion offers breathtaking views, live music, and complimentary drinks and appetizers, all for $79.95 per person.
With a rating of 4.7 out of 5 based on 137 reviews, this cruise is a well-organized and valuable experience. Guests rave about the transportation, service, and overall enjoyment, with one reviewer noting they were “drunk by the time we got back!”
While not suitable for those prone to seasickness, this sunset sail is an excellent way to soak in the Key West atmosphere and witness a stunning Florida sunset.
Read our full review: Key West: Sunset Party Cruise by Catamaran Review
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2-Hour Sunset Sailing With Wine In Stock Island
The allure of a serene sunset sail coupled with the opportunity to savor a thoughtful selection of wines beckons travelers to the 2-hour Stock Island experience.
With a 100% traveler recommendation and a Badge of Excellence, this tour offers an unmatched setting to unwind and indulge.
Guests can look forward to enjoying eight varieties of wine, five types of beer, and a delectable charcuterie board as they take in the stunning views of Key West from the water.
Accommodating up to 20 travelers aged 13 and above, this experience provides an intimate and exclusive setting, perfect for couples, friends, or solo adventurers seeking a taste of Key West’s enchanting sunset.
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Key Wests Locals Top Sailing and Sun Experience
A top sailing and sun experience among locals in Key West, this 5-hour excursion provides a well-rounded taste of the island’s coastal charm.
Reviewers praise the professional crew and delightful breakfast, lunch, and open bar offerings. While most guests rave about the smooth sailing and snorkeling, a few reported issues with organization and shallow waters.
With a maximum of 40 travelers, this intimate sailing trip allows ample time to soak up the island’s laid-back atmosphere.
Those seeking a relaxing day on the water with food and drinks included will find this experience to be a great value, though caution is advised for average swimmers given the potentially strong currents.
Read our full review: Key Wests Locals Top Sailing and Sun Experience Review
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Private 90-Minute Harbor Sailing Charter in Key West
With a private charter from Sunset Sail Key West, travelers can take in the picturesque harbor of Key West aboard a 90-minute sailing excursion.
Priced from $314.66 for groups of up to 6 people, the experience includes a knowledgeable captain and mate, soft drinks, and bottled water. Guests can also bring their own alcoholic beverages.
The charter departs from the Sunset Sail Key West dock, just steps away from the Schooner Wharf Bar.
While some past customers reported issues with booking through third-party sites, the experience itself has earned overwhelmingly positive reviews, with guests praising the crew’s expertise and the overall sailing adventure.
Read our full review: Private 90-Minute Harbor Sailing Charter in Key West Review
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Luxury Sailing Catamaran – Private Charters, Owner-Operated
Frequently, travelers to Key West seek a more intimate and exclusive sailing experience that sets them apart from the typical crowded boat tours.
Bimini Charters offers just that with their private 3-hour catamaran charters for up to six people. Highly recommended by 100% of their travelers, these owner-operated tours provide a personalized sailing experience along the Key West coastline.
Guests can bring their own food and drinks, while enjoying complimentary sparkling wine, soda, and water.
With a 5.0 rating and a Badge of Excellence, Bimini Charters is an ideal choice for special occasions, offering an excellent sailing and snorkeling experience with a friendly and knowledgeable crew.
Read our full review: Luxury Sailing Catamaran – Private Charters, Owner-Operated Review
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Private Luxury Catamaran Sunset Sails
Although Bimini Charters offers a range of sailing experiences, their private luxury catamaran sunset sails stand out as a truly exceptional offering.
For ₹67,259.81, groups of up to 6 can enjoy a 3-hour sunset sail on a private catamaran, complete with soft drinks, water, and a bottle of sparkling wine.
The tour departs from the convenient location 100 yards past Hogfish Bar and Grill in Key West, and returns to the same spot.
With a perfect 5-star rating based on one review, this sunset sail promises an unforgettable experience for those seeking a luxurious and private way to enjoy the beauty of Key West’s coastline.
Read our full review: Private Luxury Catamaran Sunset Sails Review
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Frequently Asked Questions
Is Seasickness a Common Issue on Key West Sailing Tours?
Seasickness can be a common issue on sailing tours, but the risk depends on various factors like weather conditions, boat size, and individual susceptibility. Experienced tour operators often provide remedies and advice to help minimize discomfort for passengers.
What Attire Is Recommended for Sailing in Key West?
Comfortable, lightweight clothing and closed-toe shoes are recommended for sailing in Key West. Sun protection like hats, sunglasses, and sunscreen are also essential to stay cool and protected from the elements during the excursion.
Can I Bring My Own Food and Drinks on the Sailing Tours?
Passengers can generally bring their own food and drinks on sailing tours in Key West. However, it’s best to check with the tour operator beforehand as some may have restrictions or provide refreshments as part of the experience.
Are There Any Age or Physical Limitations for the Sailing Experiences?
Most sailing tours in Key West don’t have strict age or physical limitations, but participants should be able to get on and off the boat safely. Some tours may have minimum age requirements or restrictions for young children.
What Are the Refund Policies if the Sailing Tour Is Cancelled?
Most sailing tour operators offer full refunds if the tour is cancelled due to weather or other unforeseen circumstances. Customers should check the specific refund policy before booking to understand their options in case of a cancellation.
Recap
The diverse sailing experiences in Key West offer something for all, from sunset cruises with cocktails to private charters on luxury catamarans. Whether you’re seeking a lively party atmosphere or a more intimate, serene voyage, there are plenty of options to choose from to create an unforgettable day on the water. With stunning sunsets, local cuisine, and the chance to spot marine life, these sailing adventures showcase the best of what Key West has to offer.