Sailing in Key West delivers memorable experiences without breaking the bank. The most worthwhile options include a 2-hour sunset champagne cruise (perfect for photos and wildlife spotting), and the morning reef snorkel tours (best water visibility, fewer crowds). I’m especially fond of the wine-tasting sunset sail – it’s intimate and includes quality local appetizers that complement the experience beautifully. Budget-conscious travelers should stick with group catamarans, while families might prefer private charters for flexibility with kids. After decades of exploring these waters, these are my favorite Key West sailing tours worth your time and money.
Let’s check out the top sailing excursions available:
Good To Know
- Key West offers a variety of sunset cruises, including a 2-hour catamaran journey with an impressive 92% recommendation rate.
- Snorkeling adventures provide the opportunity to explore the diverse marine life and underwater wonders of Key West.
- Sunset sailing with wine tasting experiences offer an intimate and enchanting setting, catering to oenophiles and sunset enthusiasts.
- Private and luxury charters provide personalized service and memorable sailing experiences, perfect for special occasions.
- Combo tours in Key West offer a full-day of water sports and activities, culminating in a sunset catamaran cruise with an open bar.
Key West Sunset Champagne Catamaran Cruise
The Key West Sunset Champagne Catamaran Cruise offers travelers a 2-hour journey aboard a 69-foot catamaran as they soak in the breathtaking sunset views over the turquoise waters.
With 570 reviews and a 92% recommendation rate, this popular cruise provides an enjoyable experience for up to 86 guests. Included in the cruise are drinks such as beer, wine, champagne, and soft drinks, as well as a restroom on board.
While gratuities aren’t included, all taxes and fees are covered. Travelers have praised the friendly crew and stunning scenery, though some have noted issues with communication and value for upgrades.
Read our full review: Key West Sunset Champagne Catamaran Cruise Review
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Key West Multi-Stop Reef Snorkeling Boat Tour by Catamaran
Offering a double-dip adventure, the Key West Multi-Stop Reef Snorkeling Boat Tour by Catamaran allows travelers to explore two vibrant reef locations and marvel at the diverse marine life below the surface.
Awarded a Badge of Excellence and boasting a 93% recommendation rate from reviewers, this tour provides an efficient and enjoyable snorkeling experience. Guests will travel aboard a speedy catamaran, receive professional instruction and top-quality gear, and indulge in complimentary beer and wine after their underwater explorations.
With daytime and sunset options available seasonally, this tour caters to various preferences and promises an unforgettable glimpse into the underwater wonders of Key West.
Read our full review: Key West Multi-Stop Reef Snorkeling Boat Tour by Catamaran Review
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2-Hour Sunset Sailing With Wine In Stock Island
Aboard a captivating sunset sail in Stock Island, Key West, travelers can indulge in an enchanting experience complete with appetizers, a variety of wines, and breathtaking views.
This 2-hour tour is highly recommended, boasting a 100% traveler satisfaction rate and a Badge of Excellence. Savor charcuterie boards featuring meats, cheeses, crackers, and chocolate, as well as five types of beer and complimentary bottled water.
With a maximum of 20 passengers, this tour offers an intimate setting for sipping on eight wine varieties while watching the sun dip below the horizon.
Conveniently located near public transportation, this sailing adventure is a must-try for oenophiles and sunset enthusiasts alike.
Read our full review: 2-Hour Sunset Sailing With Wine In Stock Island Review
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Luxury Sailing Catamaran – Private Charters, Owner-Operated
Bimini Charters offers a truly luxurious sailing experience aboard their private 3-hour catamaran tours in Key West. For $750, groups of up to 6 can enjoy an incredible 5-star rated outing, complete with complimentary beverages and the freedom to bring their own snacks and cocktails.
The friendly, attentive crew ensures a relaxing atmosphere while providing insightful commentary about the area. Passengers rave about the excellent sailing, memorable snorkeling at local reefs, and the intimate setting that enhances the overall experience.
Whether celebrating a special occasion or simply seeking a luxurious day on the water, Bimini Charters’ private catamaran tour is an exceptional choice for those seeking the best sailing in Key West.
Read our full review: Luxury Sailing Catamaran – Private Charters, Owner-Operated Review
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Key Wests Locals Top Sailing and Sun Experience
For those seeking a quintessential Key West sailing experience, the highly-rated “Key West’s Locals’ Top Sailing and Sun” tour delivers an exceptional day on the water.
With a maximum of 40 travelers, this sailing excursion offers a more intimate and personalized experience compared to larger group tours. Guests can enjoy a full continental breakfast, a hearty buffet lunch, and an open bar with mimosas, beer, wine, and sangria.
The tour’s 4.0 rating across Viator and Tripadvisor suggests that most travelers have had great experiences, praising the knowledgeable crew, the serene sailing, and the snorkeling highlights.
However, some have reported organizational issues and last-minute cancellations, underscoring the importance of clear communication about the tour’s details and expectations.
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
Conveniently located near the Schooner Wharf Bar, the Private 90-Minute Harbor Sailing Charter in Key West provides a compact yet captivating sailing experience.
Recommended by 94% of travelers, the charter boasts a 5.0 rating from 16 reviews. For $314.66 per group (up to 6 people), guests enjoy a private sail with a captain and mate, along with complimentary soft drinks, bottled water, and gratuities.
Alcoholic drinks can be brought onboard. The experience includes hotel pickup and drop-off, and offers free cancellation up to 24 hours in advance.
While the booking process through Viator has drawn some criticism, customers highlight the great crew, ability to bring personal items, and enjoyable conversations during the sail.
Read our full review: Private 90-Minute Harbor Sailing Charter in Key West Review
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Private Luxury Sailing Catamaran Sunset Sails
Sailing into the stunning Key West sunset aboard a private luxury catamaran is a truly breathtaking experience.
Operated by Bimini Charters, this 3-hour private tour accommodates up to 6 participants and costs €746.32 per group. Guests can enjoy soft drinks, water, and a bottle of sparkling wine as they sail past the picturesque harbor.
The tour departs at 5:00 PM from a location just 100 yards past the Hogfish Bar and Grill, and returns to the same point. While not wheelchair accessible, the tour is suitable for most travelers.
With a perfect 5-star rating based on Viator and Tripadvisor reviews, this private sailing excursion is an exceptional way to experience the beauty of Key West from the water.
Read our full review: Private Luxury Sailing Catamaran Sunset Sails Review
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Key West: Smathers Beach & Activities With a Sunset Catamaran & Open Bar
Visitors to Key West can enjoy a full-day combo tour that combines the pleasures of Smathers Beach’s unlimited water sports with a breathtaking sunset sail aboard a catamaran.
The tour includes snorkeling, kayaking, paddleboarding, parasailing, and sunbathing, followed by a sunset cruise with an open bar and live music.
Roundtrip transportation from Miami is provided, and the sunset cruise check-in is at 4:15 PM.
The tour is limited to a maximum of 90 travelers and is priced at $229.99 per person, with free cancellation up to 24 hours before the experience.
While the tour is stroller accessible, it isn’t wheelchair accessible.
Read our full review: Key West: Smathers Beach & Activities With a Sunset Catamaran & Open Bar Review
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Frequently Asked Questions
Can I Bring My Own Food and Drinks on the Cruise?
Passengers are typically allowed to bring their own food and drinks on most cruises. However, it’s always best to check the cruise operator’s policies beforehand to ensure you can enjoy your own provisions during the sailing experience.
Do I Need to Know How to Sail to Participate?
No, you don’t need to know how to sail to participate. Most sailing experiences in Key West provide knowledgeable crew who’ll guide you through the sailing process. All you need is a sense of adventure and a willingness to learn.
Are There Any Age or Physical Requirements for the Tours?
Age and physical requirements for sailing tours can vary, but many offer accommodations for a wide range of participants. It’s best to check with the tour operator to understand any specific guidelines or limitations before booking.
Can I Book a Private Sailing Experience for a Special Event?
Yes, you can book a private sailing experience for a special event. Many sailing tour companies in the area offer customizable private charters that can accommodate groups of various sizes for celebrations, corporate outings, or other special occasions.
What Is the Cancellation Policy in Case of Inclement Weather?
The cancellation policy typically allows for full refunds if a sailing tour is cancelled due to inclement weather. Operators want to ensure customers have the best possible experience, so they’re flexible in accommodating changes beyond their control.
The Sum Up
Key West offers a variety of exceptional sailing experiences, from sunset cruises and snorkeling tours to private charters and harbor sails. Whether you’re looking for a romantic sunset or an adventure-filled day on the water, there’s something for all. With a range of options to choose from, you’re sure to find the perfect sailing adventure to make your Key West visit unforgettable.