
Key West Sunset Sail Aboard Legendary Schooner Appledore
Traveler rating
5.0/5
Based on 368 traveler reviews. Ratings and reviews provided by Viator and Tripadvisor.
Quick answer
Is Key West Sunset Sail Aboard Legendary Schooner Appledore worth booking?
Key West Sunset Sail Aboard Legendary Schooner Appledore is a 2-hour experience in Key West, United States, from $89 per person. It scores 85 out of 100 on the Outty Ranking, which we label “Exceptional”, based on a 5/5 rating across 368 reviews. Cancellation is free up to 24 hours before the start time. Same-day spots are currently showing.
- Outty Ranking
- 85 / 100
- Rating
- 5/5 (368)
- Duration
- 2 hours
- From
- $89 per person
Experience sailing Key West on a majestic 2-masted schooner, just like adventurers from the 19th century, while enjoying the luxurious state-of-the-art accommodations of a modern passenger schooner. Her decks are spacious and comfortable. We limit passengers to just 36, guaranteeing you'll have room to move about and have an intimate evening experience. Feel the sense of adventure as the crew hoists the sails. Participate in this age-old tradition by helping raise the sails. Take a turn at the wheel and feel the exhilaration of captaining a traditional tall ship. With the painted sky as an exquisite backdrop, your sunset sail takes you past Key West’s Historic Seaport, Mallory Square’s Sunset Celebration, the Navy Mole where the big ships dock and the civil war era Fort Zachary Taylor. Soak in these sights while enjoying a glass of premium wine, an icy cold premium beer, full cocktail bar or soft drinks.
What you get
About this experience
Experience sailing Key West on a majestic 2-masted schooner, just like adventurers from the 19th century, while enjoying the luxurious state-of-the-art accommodations of a modern passenger schooner. Her decks are spacious and comfortable. We limit passengers to just 36, guaranteeing you'll have room to move about and have an intimate evening experience. Feel the sense of adventure as the crew hoists the sails. Participate in this age-old tradition by helping raise the sails. Take a turn at the wheel and feel the exhilaration of captaining a traditional tall ship. With the painted sky as an exquisite backdrop, your sunset sail takes you past Key West’s Historic Seaport, Mallory Square’s Sunset Celebration, the Navy Mole where the big ships dock and the civil war era Fort Zachary Taylor. Soak in these sights while enjoying a glass of premium wine, an icy cold premium beer, full cocktail bar or soft drinks.
What's included
Included
- Carbonated beverages
- Snacks
- Alcoholic beverages
- Sunset sail aboard a classic wooden Schooner that has circumnavigated the globe
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.
Pass by without stopping
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.
Pass by without stopping
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.
Pass by without stopping
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
- Service animals allowed
- 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 367 traveler reviews. Written by us, not quoted from reviewers.
Food and drink
5 mentionsThe tastings and food stops are a highlight for most reviewers.
Photo opportunities
2 mentionsThe views and photo stops come up again and again.
Traveler reviews
367 verified traveler reviews for Key West Sunset Sail Aboard Legendary Schooner Appledore. Ratings and reviews provided by Viator and Tripadvisor.
Ready to go again!
Fantastic ..Joe & Christina were absoulutly the best. Drinks ..snacks best we've had on the island.
via Tripadvisor
Wonderful Sunset Sail
We had a wonderful time on this sunset sail. Captain Joe and Cristina were friendly, efficient and professional. The drink was plentiful with both alcohol and non alcohol choices and the snacks were delicious. We had a medical emergency which required us to return to port which the captain and crew handled with aplomb. We were able to complete our excursion after leaving the port. Highly recommended!
via Tripadvisor
Amazing trip!!
Absolutely amazing!! Captain Joe and Christina were so great!! Great day!! Great food and the sangria was delicious!! We are already planning our next trip!!
Response from the operator: Joe and Cristina will be thrilled to know you enjoyed their sail! We can't wait to see you back again!
via Tripadvisor
A beautiful night!
This tour was amazing! The boat was beautiful and the crew amazing!! My husband and I took this and very happy we did it made our key west trip so memorable!!!
Response from the operator: Thank you for the wonderful review! We are thrilled we got to be part of your Key West experience.
via Viator
Sunset cruise
The view was amazing . Captain Joe and his crew Vitali and Jordan were super nice and attentive . Boat ride was smooth and beautiful. Highly recommended
Response from the operator: Thank you for the recommendation and the great review!
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
- 129
- Verdict
- Exceptional
Who runs this experience
Operated by Key West Schooners, who run 3 experiences we rank across 1 city, with an average Outty Ranking of 81.1.
See everything Key West Schooners runsWhy this scores 85
The Outty Ranking is a weighted composite. Here is how this experience performed on each component.
Key West Sunset Sail Aboard Legendary Schooner Appledore: questions travelers ask
Practical detail on this experience, plus the wider planning questions for Key West.
How much does Key West Sunset Sail Aboard Legendary Schooner Appledore cost?
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Prices start at $89 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 Sunset Sail Aboard Legendary Schooner Appledore 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 Sunset Sail Aboard Legendary Schooner Appledore 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 (5/5 across 368 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 Key West Sunset Sail Aboard Legendary Schooner Appledore?
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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 Sunset Sail Aboard Legendary Schooner Appledore 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 Sunset Sail Aboard Legendary Schooner Appledore?
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Around 129 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 Sunset Sail Aboard Legendary Schooner Appledore 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 Sunset Sail Aboard Legendary Schooner Appledore?
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Included: Carbonated beverages; Snacks; Alcoholic beverages; and Sunset sail aboard a classic wooden Schooner that has circumnavigated the globe. Not included: Gratuity. Always check the voucher for the final list before you travel.
Where is the meeting point for Key West Sunset Sail Aboard Legendary Schooner Appledore?
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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. Hotel pickup is not included, so plan your own transport and arrive 15 minutes early.
What languages is Key West Sunset Sail Aboard Legendary Schooner Appledore 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 Sunset Sail Aboard Legendary Schooner Appledore?
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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.
Is Key West Sunset Sail Aboard Legendary Schooner Appledore wheelchair or stroller accessible?
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The operator notes: Infants are required to sit on an adult’s lap. If accessibility is critical, contact the operator after booking to confirm arrangements for your date.
What happens to Key West Sunset Sail Aboard Legendary Schooner Appledore 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 Sunset Sail Aboard Legendary Schooner Appledore?
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Across 368 reviews averaging 5.0 out of 5, recurring themes include food and drink, photo opportunities. The tastings and food stops are a highlight for most reviewers.
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