
Key West Small-Group Sunset Sail with Wine and Hors d'oeuvres
Traveler rating
4.9/5
Based on 1,483 traveler reviews. Ratings and reviews provided by Viator and Tripadvisor.
Quick answer
Is Key West Small-Group Sunset Sail with Wine and Hors d'oeuvres worth booking?
Key West Small-Group Sunset Sail with Wine and Hors d'oeuvres is a 2-hour experience in Key West, United States, from $135 per person. It scores 85 out of 100 on the Outty Ranking, which we label “Exceptional”, based on a 4.9/5 rating across 1,483 reviews. Cancellation is free up to 24 hours before the start time. Same-day spots are currently showing.
- Outty Ranking
- 85 / 100
- Rating
- 4.9/5 (1,483)
- Duration
- 2 hours
- From
- $135 per person
The Wind & Wine Sunset Sail offers a boutique experience unlike any other in Key West! This isn’t your typical party boat—it’s a calm, uncrowded sail aboard a historic schooner with an intimate, relaxed vibe. You’ll enjoy a guided tasting of fine wines from around the world, along with a selection of craft and domestic beers and light hors d'oeuvres including crudites, meats, cheeses, crackers, fruit, and chocolate. With small group sizes, there’s plenty of space to move around and enjoy the view without the crowds. It’s perfect for a romantic date or a fun evening with friends—upscale, but never uptight. What really sets this trip apart is the crew. They’re fun, welcoming, and passionate about what they do—ready to pour your next glass, share a story, or make sure you’re having a great time. Add in a Key West sunset, and you’ve got one of the most unique and enjoyable evenings on the water!
What you get
About this experience
The Wind & Wine Sunset Sail offers a boutique experience unlike any other in Key West! This isn’t your typical party boat—it’s a calm, uncrowded sail aboard a historic schooner with an intimate, relaxed vibe. You’ll enjoy a guided tasting of fine wines from around the world, along with a selection of craft and domestic beers and light hors d'oeuvres including crudites, meats, cheeses, crackers, fruit, and chocolate. With small group sizes, there’s plenty of space to move around and enjoy the view without the crowds. It’s perfect for a romantic date or a fun evening with friends—upscale, but never uptight. What really sets this trip apart is the crew. They’re fun, welcoming, and passionate about what they do—ready to pour your next glass, share a story, or make sure you’re having a great time. Add in a Key West sunset, and you’ve got one of the most unique and enjoyable evenings on the water!
What's included
Included
- Light refreshments
- Wine tasting
- Unlimited beer, wine and soft drinks
- Hors d'oeuvres complementing the wines
Not included
- Gratuities
What you'll see and do
Danger Charters
Check-In at our storefront 1/2 hour before departure
20 minutes here
Key West
Sailing nightly, we serve eight different fine wines from all over the world, usually four red, three white, and a Champagnoise. Wine drinkers love this cruise since it is virtually the only sailing excursion in the U.S. that serves “real” wine. In addition, an array of quality beer, and hors-d'oeuvres are also served, making the evening an unforgettable start to a great Key West night!
100 minutes here
Where it starts and ends
Meeting point
Key West
Please arrive 30 minutes prior to your departure to check in. We are located at the base of the Opal Key Resort. Walk up the ramp between the Resort and the Art Museum and we will be the second shop on the left
Hotel pickup
No pickup: everyone meets at the start point.
Ends at
Please arrive 30 minutes prior to your departure to check in. We are located at the base of the Opal Key Resort. Walk up the ramp between the Resort and the Art Museum and we will be the second shop on the 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 15 travelers per booking
- Operated by
- Danger Charters
Know before you go
- Public transportation options are available nearby
- Suitable for all physical fitness levels
- Minimum drinking age is 21 years
- Must be 13 or older for this trip.
Photos






What travelers are saying
Outty’s summary of the themes that recur across 1,482 traveler reviews. Written by us, not quoted from reviewers.
Food and drink
7 mentionsThe tastings and food stops are a highlight for most reviewers.
Photo opportunities
2 mentionsThe views and photo stops come up again and again.
Value for money
2 mentionsTravelers feel they got more than they paid for.
Traveler reviews
1,482 verified traveler reviews for Key West Small-Group Sunset Sail with Wine and Hors d'oeuvres. Ratings and reviews provided by Viator and Tripadvisor.
Would recommend
Enjoyable trip. Great wines and food, crew were very helpful and friendly. Would recommend, a great trip.
via Viator
Beautiful mood setting cruise
Excellent sunset cruise. Group was smaller and wine was great! Preferred this over larger group cruise
via Tripadvisor
Sunset in Key West
Great experience, a little warm at first, but be patient, once under way, the experience starts and how wonderful it will be. If you’re concerned about the best side of the ship to choose, don’t be, the captain will navigate the vessel so everyone gets to view the sunset.
via Viator
Highly enjoyable!
This is a beautiful sailboat and a wonderful cruise. There was great customer service and a wonderful selection of wine and small bites. Highly recommended!
via Viator
Great Sunset Sail and Wine-tasting!
What an incredible experience! We enjoyed an amazing Sunset Sail, which also included witnessing from a safe distance a thunderstorm around Key West. That was an added bonus. Thank you to Captain Mike and crew for keeping us safe and entertained throughout the sail. Great wine selections to go with our incredible views of the sunset!
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
- 519
- Verdict
- Exceptional
Who runs this experience
Operated by Danger Charters, who run 6 experiences we rank across 1 city, with an average Outty Ranking of 73.0 and 1 in the 90+ Club.
See everything Danger Charters runsWhy this scores 85
The Outty Ranking is a weighted composite. Here is how this experience performed on each component.
Key West Small-Group Sunset Sail with Wine and Hors d'oeuvres: questions travelers ask
Practical detail on this experience, plus the wider planning questions for Key West.
How much does Key West Small-Group Sunset Sail with Wine and Hors d'oeuvres cost?
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Prices start at $135 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 Key West Small-Group Sunset Sail with Wine and Hors d'oeuvres 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 Key West Small-Group Sunset Sail with Wine and Hors d'oeuvres worth it?
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It holds an Outty Ranking of 85 out of 100, which we label "Exceptional". That score blends traveler sentiment (4.9/5 across 1,483 reviews), the depth of that review evidence, recent booking momentum, value for money against comparable most popular in Key West, and how flexible the cancellation terms are.
Can I cancel or reschedule Key West Small-Group Sunset Sail with Wine and Hors d'oeuvres?
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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 Key West Small-Group Sunset Sail with Wine and Hors d'oeuvres 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 Key West Small-Group Sunset Sail with Wine and Hors d'oeuvres?
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Around 519 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 Key West Small-Group Sunset Sail with Wine and Hors d'oeuvres 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 Guided Bike Tour of Old Town Key West, Half-Day Trip from Key West with Kayaking, Snorkeling & Sunset, Shark and Wildlife Viewing Adventure in Key West. 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.
What is included in Key West Small-Group Sunset Sail with Wine and Hors d'oeuvres?
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Included: Light refreshments; Wine tasting; Unlimited beer, wine and soft drinks; and Hors d'oeuvres complementing the wines. Not included: Gratuities. Always check the voucher for the final list before you travel.
Where is the meeting point for Key West Small-Group Sunset Sail with Wine and Hors d'oeuvres?
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Please arrive 30 minutes prior to your departure to check in. We are located at the base of the Opal Key Resort. Walk up the ramp between the Resort and the Art Museum and we will be the second shop on the left Hotel pickup is not included, so plan your own transport and arrive 15 minutes early.
What languages is Key West Small-Group Sunset Sail with Wine and Hors d'oeuvres offered in?
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It runs in English. Pick your language when choosing a date and time, as not every departure runs in every language.
Will I get instant confirmation and a mobile ticket for Key West Small-Group Sunset Sail with Wine and Hors d'oeuvres?
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Confirmation is sent by the operator after booking, usually within 48 hours; if it is not confirmed you are not charged. Mobile tickets are accepted, so you can show the voucher on your phone.
What happens to Key West Small-Group Sunset Sail with Wine and Hors d'oeuvres if the weather is bad?
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This experience depends on good weather. If it is canceled because of poor weather, you are offered a different date or a full refund.
What do travelers say about Key West Small-Group Sunset Sail with Wine and Hors d'oeuvres?
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Across 1,483 reviews averaging 4.9 out of 5, recurring themes include food and drink, photo opportunities, value for money. The tastings and food stops are a highlight for most reviewers.
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