
Classic Key West Schooner Sunset Sail with Full Open Bar
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September 2026
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Who is going?
Adults
Age 13 and over
Children
Age 12 and under
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Free cancellation up to 24 hours before. Same price on Viator, Outty earns a commission.
Traveler rating
4.9/5
Based on 266 traveler reviews. Ratings and reviews provided by Viator and Tripadvisor.
Quick answer
Is Classic Key West Schooner Sunset Sail with Full Open Bar worth booking?
Classic Key West Schooner Sunset Sail with Full Open Bar is a 2-hour experience in Key West, United States, from $109 per person. It scores 78 out of 100 on the Outty Ranking, which we label “Strongly Recommended”, based on a 4.9/5 rating across 266 reviews. Cancellation is free up to 24 hours before the start time. Same-day spots are currently showing.
- Outty Ranking
- 78 / 100
- Rating
- 4.9/5 (266)
- Duration
- 2 hours
- From
- $109 per person
There's no better way to savor the magic of a Key West sunset than aboard a majestic schooner, complete with a full open bar. This enchanting journey blends the timeless elegance of traditional sailing with the lively sp
What you get
About this experience
There's no better way to savor the magic of a Key West sunset than aboard a majestic schooner, complete with a full open bar. This enchanting journey blends the timeless elegance of traditional sailing with the lively spirit of Key West, promising an unforgettable experience for all. As you sail further into the sunset, the full open bar comes to life, offering an enticing array of cocktails, wines, and spirits to complement the evening's splendor. Sip on our signature Schooner Bloody Mary or Dark & Stormy as you watch the sky ignite with color. The skilled bartenders are on hand to craft your favorite drinks, ensuring that your glass is never empty as you drink in the sights and sounds of the sea. As the schooner begins its journey back to Key West, you find yourself lost in the timeless rhythm of the sea, grateful for the opportunity to witness the beauty of a Key West sunset from the deck of a historic schooner.
What's included
Included
- Carbonated beverages
- Bottled water
- In-person Guide: English
- Alcoholic beverages
Not included
- Gratuity
What you'll see and do
Key West Historic Seaport
The Key West Historic Seaport is a picturesque area located along the waterfront of Key West, Florida. It serves as both a working marina and a vibrant hub for visitors. The seaport features charming old buildings, colorful shops, restaurants, and bars, all set against the backdrop of the sparkling waters of the Gulf of Mexico.
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Mallory Square
Mallory Square is a popular waterfront area located in Key West, Florida. It's famous for its vibrant sunset celebration, where locals and visitors gather every evening to enjoy street performances, live music, and food vendors while watching the sunset over the Gulf of Mexico.
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Sunset Key is a small, private island located just off the coast of Key West, Florida. It is known for its luxurious accommodations, beautiful beaches, and stunning sunsets.
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Fort Zachary Taylor Historic State Park
Fort Zachary Taylor is a historic military fort located at the southernmost point of Key West, Florida. Constructed in the mid-19th century, it played a significant role during the Civil War and later in the Spanish-American War. The fort is named after President Zachary Taylor and is now part of the Fort Zachary Taylor Historic State Park.
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Where it starts and ends
Meeting point
Key West
Check-in is located at the far end of William Street, just to the right of the Western Union sign. From Elizabeth Street, keep the water on your left and follow Lazy Way Lane past the shops. The Marker Resort on your right, and the Schooner Wharf Bar on your left. The booth will be on your left.
Hotel pickup
No pickup: everyone meets at the start point.
Ends at
Check-in is located at the far end of William Street, just to the right of the Western Union sign. From Elizabeth Street, keep the water on your left and follow Lazy Way Lane past the shops. The Marker Resort on your right, and the Schooner Wharf Bar on your left. The booth will be on your left.
Before you book
- Cancellation
- For a full refund, cancel at least 24 hours before the scheduled departure time.
- Languages
- en
- Ticket
- Mobile Only
- Runs on
- Every day
- Group size
- Up to 12 travelers per booking
- Operated by
- Key West Schooners
Know before you go
- Public transportation options are available nearby
- Infants are required to sit on an adult’s lap
- Suitable for all physical fitness levels
- Total sailing time is 2 hours. There are no stops.
Photos






What travelers are saying
Outty’s summary of the themes that recur across 265 traveler reviews. Written by us, not quoted from reviewers.
Food and drink
4 mentionsThe tastings and food stops are a highlight for most reviewers.
Small groups
3 mentionsThe group size is repeatedly described as intimate rather than packed.
Good for families
2 mentionsReviewers traveling with kids report it landed well with their group.
Traveler reviews
265 verified traveler reviews for Classic Key West Schooner Sunset Sail with Full Open Bar. Ratings and reviews provided by Viator and Tripadvisor.
The crew of our schooner...
The crew of our schooner was knowledgeable and friendly they made the entire experience more enjoyable. We have been on many different sunset cruises over the years; this one was so peaceful and calm. It made for a beautiful evening! I would highly recommend this experience if you are looking for something a little less rowdy but with more character, it was amazing!
Response from the operator: Thank you so much for the wonderful review! ⛵🌅 We’re thrilled you enjoyed the peaceful atmosphere and found our crew knowledgeable and friendly. We love offering a relaxing sunset sail with character and a chance to truly enjoy the beauty around you. Thank you for recommending us, and we hope to welcome you aboard again!
via Viator
Sunset in Key West
My wife and I enjoyed the personable 2 hour Sunset Sail. We were very fortunate there were only 12 total on the boat. The day couldn’t have been better with clear skies a calming breeze, and a beautiful sunset. The drinks and tapas were a plus. We met a nice couple from Indiana. Christina and Capt. Joe were a perfect team. Very personable and friendly. So glad we chose this excursion.
Response from the operator: Thank you for such a wonderful review! ⛵🌅 We’re so glad you and your wife enjoyed the intimate setting, beautiful sunset, drinks, and tapas. It sounds like you had the perfect evening on the water! We’ll be sure to share your kind words with Christina and Captain Joe. We hope to welcome you aboard again soon!
via Tripadvisor
Never again
Appetizers were a joke. Good Bloody Mary , captain was short with his answers.
Response from the operator: Thank you for taking the time to share your feedback. We’re glad you enjoyed the Bloody Mary, but we’re sorry the appetizers and interaction with the captain fell short of expectations. We take your comments seriously and will share them with our team as we work to improve the experience for all our guests.
via Tripadvisor
Favorite part of our trip to Key West!
What a wonderful experience! The crew (Joe, Christina, and Roland) was fantastic - friendly and funny. We are so glad that we chose this beautiful schooner sail with a small group of people for our sunset cruise rather than going on a big party boat with loud music. The group on board was fun and laid-back. (It was a mix of couples, a group of friends, and an adult family celebrating a birthday.) The cost was very reasonable as it included about 2 hours on the water, an open bar, and appetizers. It was our favorite part of our trip to Key West!
Response from the operator: Thank you so much for this wonderful review! ⛵️ We’re thrilled to hear that your sunset sail was the favorite part of your Key West trip! 🌅 We’ll be sure to share your kind words with Joe, Christina, and Roland. We love hearing that their friendly personalities and sense of humor helped create such a fun and welcoming atmosphere for everyone aboard. It sounds like you found exactly what we hope to offer—a relaxed, intimate sailing experience where you can enjoy the sunset, good company, drinks, and appetizers without the loud party-boat atmosphere. Thank you for choosing to sail with us and for the fantastic recommendation! We hope to welcome you back aboard the Appledore on your next visit to Key West. 💙🥂⛵️
via Tripadvisor
Beautiful evening
Amazing experience from start to end. We were treated like family by the crew, provided wonderful snacks, and cocktails. Definitely recommend if you want a relaxing sail vs a party boat experience.
Response from the operator: Thank you so much for the wonderful review! ⛵️ We’re thrilled to hear your experience was amazing from start to finish and that our crew made you feel like family. That’s exactly the kind of warm, welcoming atmosphere we strive to create aboard the Appledore! We’re also glad you enjoyed the snacks, cocktails, and peaceful sailing experience. We truly appreciate your recommendation and are especially happy that the relaxed, intimate atmosphere was just what you were looking for. 🌅🥂 We hope to welcome you aboard again for another relaxing sail! 💙⛵️
via Tripadvisor
Good to know
- Duration
- 2 hours
- Free cancellation
- Up to 24h before
- Minimum age to book
- All ages
- Availability
- Bookable today
- Runs on
- Every day
- Hotel pickup
- No pickup, meet at start point
- Booked in 30 days
- 93
- Verdict
- Strongly Recommended
Why this scores 78
The Outty Ranking is a weighted composite. Here is how this experience performed on each component.
Classic Key West Schooner Sunset Sail with Full Open Bar: questions travelers ask
Practical detail on this experience, plus the wider planning questions for Key West.
How much does Classic Key West Schooner Sunset Sail with Full Open Bar cost?
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Prices start at $109 per person. The final price depends on the date, the time slot and the number of travelers, and peak weekends in Key West usually price higher than midweek mornings. Live pricing and remaining availability are confirmed on the booking screen before you pay.
How long does Classic Key West Schooner Sunset Sail with Full Open Bar take?
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Plan for about 2 hours from start to finish, not counting travel to the meeting point. Most travelers leave another 30 minutes on either side so the rest of the day in Key West is not rushed.
Is Classic Key West Schooner Sunset Sail with Full Open Bar worth it?
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It holds an Outty Ranking of 78 out of 100, which we label "Strongly Recommended". That score blends traveler sentiment (4.9/5 across 266 reviews), the depth of that review evidence, recent booking momentum, value for money against comparable last minute in Key West, and how flexible the cancellation terms are.
Can I cancel or reschedule Classic Key West Schooner Sunset Sail with Full Open Bar?
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Yes. Cancel free up to 24 hours before the start time for a full refund. Inside that window the booking is non-refundable, and no-shows are not refunded.
Is Classic Key West Schooner Sunset Sail with Full Open Bar suitable for kids and families?
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Yes, all ages are welcome. Families should still weigh the 2-hour running time, and strollers are easier on the earlier, quieter departures.
How far in advance should I book Classic Key West Schooner Sunset Sail with Full Open Bar?
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Around 93 people booked this in the last 30 days, so popular slots go early. Two to three weeks ahead is comfortable in shoulder season, while summer weekends and holidays in Key West can sell out a month out. Same-day spots do open up when other travelers cancel, so it is worth checking if you are already in town.
What should I bring or wear?
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Bring photo ID, your booking confirmation on your phone, a refillable water bottle and comfortable shoes. Dress for the weather in Key West and add a light layer if any part of the 2-hour experience runs outdoors or after sunset.
Where does Classic Key West Schooner Sunset Sail with Full Open Bar start and how do I get there?
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The exact meeting point and directions are on your voucher once you book, and they sit in central Key West within reach of public transport. Arrive 15 minutes early: late arrivals are treated as no-shows by most operators.
What are the best things to do in Key West?
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Key West is a boat town. The only living coral barrier reef in the continental US sits seven miles offshore, and reef trips, sunset catamarans and backcountry kayak runs are the core bookings, alongside Hemingway house and Duval history walks. Our ranking weighs boat capacity and reef site rotation, which separates the good operators from the party cruises. On Outty we rank every Key West experience on the same 0 to 100 scale, and alongside this one the highest scorers right now include Shark and Wildlife Viewing Adventure in Key West, Southernmost Food & Cultural Walking Tour by Key West Food Tours, Half-Day Trip from Key West with Kayaking, Snorkeling & Sunset. The city page groups everything into most popular, highest reviewed, last minute and family-friendly so you can build a day around what actually delivers.
When is the best time to visit Key West?
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December to April, dry season and calm reef water. Booking patterns follow the same curve: prices and queues climb in peak weeks, while shoulder season gives you better availability on the top-ranked experiences and more room to change plans.
How many days do you need in Key West?
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Three full days covers the headline sights without sprinting. A workable rhythm is one anchor experience each morning, such as this one, an unhurried afternoon in a single neighborhood, then a food or nightlife booking in the evening. Five days lets you add a day trip outside the city.
Do I book through Outty or through the operator?
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Outty ranks and explains the experiences, then hands you to Viator to complete the booking with the operator directly. The price is the same as booking on Viator yourself, and Outty earns an affiliate commission on the referral, which is how the rankings stay free to read.
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