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.
Out at sunset: the 6:00 PM departure is under way when the sun sets, around 6:56 PM in the coming weeks.
In demand: 34 of the next 36 departures are already sold out.
From the operator’s live schedule on Viator, checked Oct 7.
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.
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.
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.
Reviews collected by Viator and Tripadvisor
Excurgo comparison of 347 Viator tours, recalculated daily.
For a full refund, cancel at least 24 hours before the scheduled departure time.
Key West Sunset Sail Aboard Legendary Schooner Appledore lasts about 2 hours. The itinerary has 3 stops.
Prices start at $89 per person for this Key West experience, booked through Viator with the price shown before checkout. There is 1 booking option, so the final price depends on the option you choose.
According to the operator’s current schedule, it runs every day, starting at 4:00 PM, 4:15 PM, 4:30 PM, 4:45 PM, 6:00 PM, and 6:15 PM.
Children aged 4–11 pay from $59, adults from $89. Infants go free.
It can: 34 of the next 36 departures are already sold out, so booking ahead is a good idea.
Yes. Cancel at least 1 day before the start for a full refund. Later cancellations are non-refundable.
The meeting point is 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 is not part of this experience.
The experience is available in EN.
It is a small-group experience with a maximum of 36 participants.
Infants are required to sit on an adult’s lap
Yes, bookings are confirmed instantly.
Reviews collected by Viator and Tripadvisor
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!!
Joe and Cristina will be thrilled to know you enjoyed their sail! We can't wait to see you back again!
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!!!
Thank you for the wonderful review! We are thrilled we got to be part of your Key West experience.
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
Thank you for the recommendation and the great review!
A great experience. We have often visited Key West but never did a sunset cruise. The crew was excellent. The view and the sunset were something you would never get from standing on the dock at Mallory Square.
Thank you so much for your wonderful review! ⛵🌅 We’re thrilled to hear that you finally experienced a Key West sunset cruise and that it became such a memorable part of your visit. You’re absolutely right—there’s something truly special about watching the sun set from the water, surrounded by the beauty of Key West, with a view that simply can’t be experienced from shore. Our crew will be delighted to hear your kind words about their excellent service and hospitality. Thank you for choosing to spend your evening with us. We hope to welcome you back aboard again on your next visit to Key West for another unforgettable sunset sail! 🌊☀️😊
Very nice sail. Unfortunately, the sunset wasnt happening due to cloud cover.. The team, Joe and Christina were very engaging. Definitely recommend!
Thank you so much for your kind review! ⛵😊 While we're sorry the clouds kept the sunset hidden, we're so glad you still enjoyed your sail. Joe and Christina will be delighted to hear their friendly and engaging service made your experience memorable. Thank you for your recommendation, and we hope to welcome you back aboard for another sail soon!
What an amazing experience. I took a 19 yo, 88 yo, and my husband with me and all of talked all through dinner about what a fun outing it was. Joe and Christina were entertaining and personable, plus cautious! The small group style leads to so much chatter among guests and crew and it was the highlight of our trip so far! Highly recommend!
Thank you so much for this wonderful review! We’re thrilled to hear that guests spanning three generations all enjoyed the experience together—that’s something truly special. ⛵🌅 It’s fantastic to know the conversation continued long after you returned to shore! Joe and Cristina will be delighted to hear that their friendly, entertaining, and safety-conscious approach helped make the outing such a memorable one. We love that the smaller group atmosphere gave everyone a chance to connect, share stories, and enjoy the evening together. Hearing that it was the highlight of your trip so far means the world to us. Thank you for the recommendation, and we hope to welcome your family back aboard for another unforgettable sail in the future! 😊
10/10 absolutely LOVED and recommend this sunset cruise!! I grew up with Navy sailors, so I was ready for a nice evening. I was pleasantly surprised that the Appledore is impeccably well maintained, the crew were all extremely professional, friendly, knowledgeable, fun, and adventurous! And the free drinks and food were a big plus. We were lucky enough to have a gorgeous, clear evening that made for really magical sea and sunset viewing. And seeing plenty of dolphin, sea turtles, and tarpon running were just the icing on the cake. If you're reading this review, you're already thinking seriously about it. Lock it in while you can! You will not be disappointed. FUN FACT - we learned the Appledore summer's up in Maine around Camden, and we just happen to be traveling there in August. So we will very likely go out with this boat again. Can't wait!
Thank you so much for this incredible review! 🌅⛵ Coming from someone who grew up around Navy sailors, your comments about the Appledore being so well maintained and professionally run truly mean a lot to us. We’re thrilled to hear the crew made such a strong impression and that the whole experience—from the sailing to the food and drinks—exceeded your expectations. And wow… dolphins, sea turtles, tarpon and a magical sunset? That’s the kind of evening we wish we could bottle up for every guest. 🐬🐢✨ We also love that you discovered our summer home in Maine! How fun that your travels will line up with the Appledore there too. We’d absolutely love to welcome you aboard again in Camden this August for another unforgettable sail. Thank you again for the amazing recommendation—and for encouraging future guests to “lock it in.” 😊
Schooner Appledore was a great experience. I would give it 10 stars if I could. A very nice clean schooner. The captain and the crew went out of their way to accommodate everyone on board. I highly recommend if you are in Key West book your schooner cruise with this company.
Thank you so much for the amazing review! We’re honored by the “10 stars” and thrilled to hear the Schooner Appledore made such a great impression on you. 🌅⛵ It’s wonderful to know you appreciated the cleanliness of the schooner and the effort the captain and crew put into making everyone feel welcome and well cared for onboard. Your recommendation truly means a lot to us. Thank you for sailing with us, and we hope to welcome you back aboard the next time you’re in Key West!
Had an excellent experience with this booking. We had a great cruise in a really cool ship. The captain and crew were awesome, the drinks were flowing, and the food was perfect for the trip. My friends and I had an awesome experience.
Thank you so much for the great review! We’re thrilled to hear you and your friends had such an awesome time onboard. 🌅⛵ It’s wonderful to know you enjoyed the ship, the crew, and that everything—from the drinks to the food—helped make the cruise a memorable experience. We really appreciate you sailing with us and hope to welcome you back aboard again soon for another fantastic trip!
Great crew. Nice and relaxing sail. Great cocktails and appetizers. Saw dolphins beautiful sunset. This is a must due.
Thank you so much for the kind words! We’re thrilled to hear you had such a relaxing sail and enjoyed everything from the cocktails and appetizers to that unforgettable sunset. 🌅⛵ Seeing dolphins out on the water is always a special bonus—sounds like you really got the full Key West experience! 🐬 We truly appreciate your recommendation and hope to welcome you back aboard again soon for another “must-do” sunset sail!
| Tour | Duration | Rating | Price | |
|---|---|---|---|---|
| Key West Sunset Sail Aboard Legendary Schooner Appledore | 2 hours | 5.0 (366) | $89 | |
 Classic Key West Schooner Sunset Sail with Full Open Bar | 2 hours | 4.9 (275) | $109 | View |
 Key West Sunset Sail with Open Bar, Live Music and Hors D'oeuvres | 2 hours | 4.7 (3,861) | $75 | View |
 Key West Small-Group Sunset Sail with Wine and Hors d'oeuvres | 2 hours | 4.9 (1,482) | $135 | View |
 Key West Sunset Sail with Live Music, Drinks and Appetizers | 2 hours | 4.6 (1,049) | $73 | View |
 Sunset Sail in Key West with Beverages Included | 1h 30min | 4.9 (986) | $79 | View |
 Key West Sunset Sail: Dolphin Watching, Wine, and Tapas | 2h 30min | 4.6 (764) | $90 | View |