Key West Sunset Sail Aboard Legendary Schooner Appledore
Recommended by 100% of travelers
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Key West, USA
- 2 hours (approx.)
- Mobile ticket
- Offered in: English
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Overview
Witness orange, gold, and pink-hued skies as you set sail from the island city of Key West on this evening sailing experience. Experience views of the city as you sail by, including the historic seaport, the Navy Mole, and Mallory Square—keeping an eye out for the square’s sunset celebration—while relaxing on deck with a beer or cocktail.
- Sunset sailing experience setting off from Key West
- A chance to see Key West’s skyline from a different perspective
- Take part in the traditional raising of the sails aboard your vessel
- Beer, wine, champagne, and cocktails are included, to enhance your trip
What's Included
- Alcoholic BeveragesPremium beer, boutique wine, champagne and cocktails for guests >21 years of age
- SnacksChef's selection of Hors d'ouevres and cocktail shrimp
- Sunset sail aboard a classic wooden Schooner that has circumnavigated the globe
- Soda/Pop
- Gratuity
Meeting and Pickup
Meeting point
- 200 William St, Key West, FL 33040, USA
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.
End point
This activity ends back at the meeting point.Itinerary
Key West Historic Seaport (Pass By)
Mallory Square (Pass By)
Sunset Key (Pass By)
Additional Info
- Confirmation will be received at time of booking
- Not wheelchair accessible
- Service animals allowed
- Infants must sit on laps
- Most travelers can participate
- Total sailing time is 2 hours. There are no stops.
- This tour/activity will have a maximum of 36 travelers
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Cancellation Policy
You can cancel up to 24 hours in advance of the experience for a full refund.
Traveler Photos
Featured review
Tracie_P
The Appledore schooner sunset cruise was the absolute highlight of our trip to Key West! The crew (Pablo, Elliot & Brian) were friendly, knowledgeable, and made everyone feel welcome from the moment we stepped aboard. The schooner itself is beautiful and authentic, adding a touch of old-world charm to the journey. True sailing is way more fun than the other sunset cruise options.
We enjoyed complimentary drinks, light bites, and stunning views as the sun dipped below the horizon and our 2 hours on the cruise flew by.
Highly recommend for couples, families, and friends wanting a truly special way to experience a Key West sunset!
Reviews
5.0
based on 363 reviews
Sort by: Most insightful
William_S, May 2026
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.
Response from Host, May 2026
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!
Marianne_R, May 2026
Great crew. Nice and relaxing sail. Great cocktails and appetizers. Saw dolphins beautiful sunset. This is a must due.
Response from Host, May 2026
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!
Teresa_Z, May 2026
The Appledore crew is super friendly and welcoming. This was our 2nd trip with them and once again they were AMAZING. Captain Will amazing.
Response from Host, May 2026
Thank you so much for sailing with us again! We’re thrilled to hear your second trip aboard the Appledore was just as amazing as the first. ⛵😊
Captain Will and the crew will be so happy to hear your kind words. They truly love creating a welcoming, fun experience for everyone onboard, and it means a lot to have returning guests like you.
We really appreciate your continued support and can’t wait to welcome you back aboard for trip number three! 🌅
Betty_D, Apr 2026
Such a great time! We really enjoyed it and got some awesome pics. Sunset over the water with othe sailing ships nearby were gorgeous!
Response from Host, May 2026
That sounds absolutely beautiful! 🌅⛵
We’re so glad you had such a great time and got some awesome photos—that’s one of the best parts of a sunset sail, especially with all the other boats out on the water adding to the view.
Thank you for joining us, and we hope to see you back aboard again soon for more unforgettable sunsets!
Lorraine_B, Apr 2026
It was amazing. The others on the boat were so fun and the charter staff were amazing, serving us drinks hors d'oeuvres. A perfect evening.😊
Response from Host, May 2026
Thank you so much for sharing this! We’re thrilled to hear you had such an amazing evening on the water. It’s great when everything comes together like that—the crew taking care of drinks and hors d’oeuvres, plus a fun group onboard really makes it special. 😊⛵
We’re so glad it felt like a perfect evening for you, and we’d love to welcome you back aboard anytime for another one!
Krista_T, Apr 2026
Excellent adventure. Enjoyed it thoroughly. The crew was personable and fun! You will be glad you did this!
Response from Host, May 2026
Thank you so much! We’re really glad to hear you had such an excellent adventure and enjoyed your time with the crew—they’ll love hearing that they helped make it fun and memorable. ⛵
We truly appreciate you sailing with us and are so happy it was an experience you thoroughly enjoyed. Hope to see you back aboard again for another great trip soon! 🌅
Matt_T, Apr 2026
We were lucky enough to be part of the reenactment of the Conch Republic Bloody Battle . Thought it was a sunset cruise when we booked, it because of the date - the boat was participating . Turned out to be a blast for the whole family , and we still had an amazing sunset to watch too!
Response from Host, May 2026
What an incredible surprise experience! We’re so glad you were able to be part of the Conch Republic Bloody Battle reenactment—it’s definitely not your average sunset cruise! ⚓🎉
It’s wonderful to hear the whole family had such a blast and that you still got to enjoy a beautiful Key West sunset at the same time. Those unique moments are what make trips like this so memorable.
Thank you for sailing with us, and we’d love to welcome you back aboard for another adventure soon! ⛵🌅
Jeff_C, Apr 2026
Nice attentive crew. Enjoyable sail. Can get pretty windy depending on the weather. Crew was very informative about the schooner as well.
Response from Host, May 2026
Thank you for the kind review! We’re so glad you enjoyed the sail and appreciated our attentive crew. They love sharing the history and details of the schooner to help make the experience even more memorable.
And yes—Mother Nature definitely likes to remind us who’s in charge sometimes! A little extra wind can certainly add to the adventure. ⛵💨
We truly appreciate you sailing with us and hope to welcome you back aboard again soon!
Scott_B, Apr 2026
Had a great time on the sunset cruise. Staff was fun, and served up great snacks and drinks. And perfect weather with a beautiful ocean sunset made it magical.
Response from Host, Apr 2026
Thank you so much for sailing with us! We’re thrilled to hear you had a great time and that our crew helped make the experience fun and enjoyable. It sounds like you caught one of those perfect Key West evenings—great weather, beautiful sunset, and a little magic on the water.
We truly appreciate you joining us and hope to welcome you back aboard again soon! ⛵🌅
Darlene_H, Apr 2026
Definitely worth it have been to Mallory Square many times for the sunset, but this was extraordinary! I loved the boat, not a large gathering of people, but we had so much fun with everybody that was on board. There is a bathroom and there are plenty of seats, but no backing for those who have a bad back. Mary and her female crew were amazing. It was very interesting to watch them. Get the ship into sail. Great drink, selection and appetizers.!
Response from Host, Apr 2026
Thank you so much for sharing your experience! We’re thrilled to hear that your sail stood out even compared to Mallory Square—what a compliment! It’s great that you enjoyed the smaller group setting, the drinks, appetizers, and watching the crew bring the ship to sail.
Captain Mary and her crew will love hearing your kind words. We also appreciate the note about seating and will keep that in mind. We hope to welcome you back aboard for another unforgettable sunset! ⛵🌅
Dale_B, Apr 2026
Great time aboard the Appledore Two. Interesting history of the boat. Crew ( Andy and Molly) were very friendly, chatting, answering questions, serving drinks. Water, some mixed drinks, sodas, beer available and plentiful. Just the right amount of people on board. Appetizers were much better than expected (shrimp cocktail, caprese stick, crostini w/dip and key lime tart).
Enjoyed our time. Smooth night to sail, sails were up. Sun set behind some clouds but can’t predict that. No a boozy sunset cruise, just lovely.
Response from Host, Apr 2026
Thank you so much for the thoughtful review! We’re delighted to hear you had such a great time aboard the Appledore II and enjoyed learning about her history—it really adds to the experience.
Andy and Molly will be so happy to hear your kind words. They love connecting with guests and making sure everyone feels welcome and well taken care of. We’re also glad the drinks and appetizers exceeded expectations—those little details make a big difference!
It sounds like you had a beautifully smooth sail, even if the sunset played a little shy behind the clouds. As you said, that’s part of the adventure! We’re so glad you appreciated the relaxed, laid-back atmosphere—it’s exactly what we aim for.
Thank you again for sailing with us, and we’d love to welcome you back aboard for another lovely evening on the water. ⛵🌅
Amy_S, Apr 2026
The Appledore Schooner is a beautiful, historic ship with huge wind sails - a sight to see. Our captain, Joe, was very professional and knowledgeable, and also fun! The crew, Molly and Andy, were very skilled and fascinating to watch. We loved the drinks and snacks. During the cruise, we saw pelicans, dolphins, an incredible rainbow, and a breathtaking sunset. The cruise was extremely relaxing and beautiful - a once in a lifetime experience that we would highly recommend!
Response from Host, Apr 2026
Thank you so much for this incredible review! We’re thrilled to hear how much you enjoyed your time aboard the Appledore—she truly is a special and historic vessel, and even more magical under full sail.
Captain Joe, along with Molly and Andy, will be so happy to hear your kind words. They love what they do, and it’s wonderful to know their skill and enthusiasm helped make your experience so memorable.
Pelicans, dolphins, a rainbow and a stunning sunset—what an unforgettable combination! 🌈🐬🌅 We’re so glad it felt like a once-in-a-lifetime experience for you.
Thank you for the recommendation, and we’d absolutely love to welcome you back aboard for another beautiful sail anytime! ⛵
Meaghan_O, Apr 2026
Great knowledgeable staff. Beautiful boat. We learned quite a bit about the Appledore and it's trip every year from Key West for winter and up to Maine for the summer.
Response from Host, Apr 2026
Thank you for the wonderful review! We’re so glad you enjoyed the beauty of the Appledore and had a chance to learn more about her seasonal journey between Key West and Maine—it’s a pretty special story.
Our crew loves sharing that knowledge and bringing the history of the vessel to life, so it’s great to hear that added to your experience. We truly appreciate you sailing with us and hope to welcome you back aboard again soon! ⛵
Courtney_L, Apr 2026
Great way to enjoy the Key West sunset. The drinks and snacks included were great and the crew was super friendly.
Response from Host, Apr 2026
Thank you for the kind words! We’re so glad you enjoyed the sunset—there’s nothing quite like a Key West evening on the water. It’s great to hear the drinks, snacks, and friendly crew all added to the experience.
We truly appreciate you sailing with us and hope to welcome you back for another beautiful sunset soon! 🌅⛵
Teri_S, Mar 2026
The crew was very nice, very informative and helpful. Great with the crowd. Sit in the middle if you don’t want to get spray by ocean water.
Response from Host, Apr 2026
Thank you so much for sharing your experience! We’re thrilled to hear you enjoyed the crew—they take great pride in being friendly, informative, and making sure everyone has a fun time on the water.
And that’s a great tip about sitting midship to stay a bit drier—nature likes to keep things exciting out there! 😊 We appreciate you sailing with us and hope to welcome you back aboard again soon.
Michael_P, Mar 2026
Great experience, friendly crew, lovely views but be prepared to get wet and be thrown about in the swell but we'll worth it.
Response from Host, Mar 2026
Thank you for your review! We’re glad to hear you enjoyed the experience, crew, and views—even with a bit of splash and sway from the swell. It’s all part of the adventure, and we’re thrilled it was worth it for you. We’d love to welcome you back aboard for another memorable sail soon! 🌊⛵🌅
Laurie_H, Mar 2026
Crew was very pleasant and accommodating. Weather was beautiful but not much wind. The crew did manage to catch a light breeze for about 20 mins. Appetizers were small but tasty and all you needed to do was ask for a drink and it was there! Only negative was it was difficult to hear the crew tell about the schooner. Would have liked to hear a bit more about its history.
Response from Host, Mar 2026
Thank you for sharing your experience! We’re glad to hear you enjoyed the beautiful weather, light sailing breeze, and that our crew made you feel welcome and well taken care of. We appreciate your feedback about wanting to hear more about the schooner’s history—it’s something we’ll keep in mind to improve future sails. We hope the tasty appetizers, drinks, and overall experience still made for a memorable outing, and we’d love to welcome you back aboard again soon! ⛵🌅
David_R, Mar 2026
The captain and crew were amazing! Very friendly, sociable and knowledgeable. Tasty hors d’oeuvres and beverages to go along with a spectacular sunset view.
Response from Host, Mar 2026
Thank you so much for your kind words! We’re thrilled to hear that our captain and crew made your evening so enjoyable. From tasty hors d’oeuvres and drinks to a spectacular sunset, it sounds like the perfect sail. We’d love to welcome you back aboard for another memorable experience soon! 🌅⛵
John_F, Mar 2026
The Sail was a Highlight of the Trip down here to Key West. The Captain was full of knowledge and knew all the pertinent history of the Ship. Plus there was a pirate battle !
Response from Host, Mar 2026
Thank you for your wonderful review! We’re thrilled to hear that your sail was a highlight of your Key West trip. Capt and crew love sharing the history of the ship, and we’re glad you enjoyed the added excitement of the pirate battle—it’s always a fun twist! We’d love to welcome you back aboard for another memorable adventure soon! ⛵🏴☠️🌅
Melinda_M, Mar 2026
Most enjoyable-crew very informative . The boat was not overcrowded which was so nice. Great way to see the ocean!
Response from Host, Mar 2026
Thank you so much for the kind review! We welcome you back for another great sail!
Ray_C, Mar 2026
Crew was awesome , great bartenders and skillful sailors .
The Sailing , drinks , food , and vibe on the Schooner was Excellent !
Response from Host, Mar 2026
So glad you had such an excellent time! Our crew takes pride in being great sailors and pretty good bartenders too. Happy to hear you enjoyed the sailing, drinks, food, and the vibe aboard the schooner. Hope to see you back on deck again soon ⛵🍹
Becky_G, Mar 2026
Awesome time on a beautiful sail boat! The crew was great! It was a nice relaxing sail with a wonderful sunset to end the day. Would definitely do it again.
Response from Host, Mar 2026
So glad you had an awesome time aboard! A relaxing sail, a great crew, and a Key West sunset is a pretty perfect combo. Thanks for sailing with us—we’d love to welcome you back for another beautiful evening on the water ⛵🌅
Margaret_Z, Mar 2026
So fun to actually sail! The crew was so hardworking, fun to be around, met everyone’s drink needs. I was so glad they also had the great Sangria as a choice. This was our second time on the Appledore and will go on the eco tour in in two days if the seas allow it. If you are looking for a relaxing sunset, choose this one.
Response from Host, Mar 2026
We love hearing from returning guests! So glad you enjoyed the sailing, the hardworking crew, and the sangria 🍷 Nothing beats a relaxing sunset on the Appledore. Fingers crossed for calm seas for your eco tour—we’ll be excited to welcome you back aboard again ⛵🌅
Susan_W, Mar 2026
We lucked out, beautiful weather for raising the sails, beautiful sunset, and full moon rise at same time. Crew was fantastic and entertaining, you can tell they love what they do.
Response from Host, Mar 2026
Sounds like the perfect night on the water! Beautiful weather, sails up, a sunset and full moon at the same time—that’s hard to beat 🌅🌕 We’re so glad you had fun with the crew. You’re right, they truly love what they do. Hope to see you back aboard again soon ⛵
Lee_G, Feb 2026
The Schooner Appledore sailboat was an amazing experience! The captain and mates were all very helpful and accommodating. We highly recommend it!
Response from Host, Mar 2026
So happy you had an amazing time aboard the Schooner Appledore! Our captain and crew will be thrilled to hear they made you feel so welcome and well taken care of. We truly appreciate the recommendation and hope to see you back on deck for another sail soon ⛵🌴
Jeff_L, Feb 2026
We've been out on with them 3 times on the tall ships and will do it again. We've met some great people each time. The sailing, crew and of course the sunset are awsome. Thanks to the crew on Appledore.
Response from Host, Feb 2026
Thank you so much for your amazing review! It’s fantastic to hear that you’ve joined us multiple times and continue to have such memorable experiences. Meeting great people, enjoying the sailing, the crew, and those stunning sunsets—that’s exactly what we hope for every guest!
We’ll be sure to pass along your thanks to the crew on Appledore. We can’t wait to welcome you back for your next adventure on the water! 🌅⛵️
John_G, Feb 2026
The excursion was everything you could imagine. Educational, Fun and breathtakingly beautiful! The crew was super!
Response from Host, Feb 2026
Thank you so much for the kind words! We’re thrilled to hear the excursion was everything you imagined—fun, educational, and beautifully memorable. That’s exactly the experience we hope every guest has with us!
We’re so glad the crew helped make your time on the water extra special. We truly appreciate you joining us and would love to welcome you back again for another unforgettable sail 🌊⛵️
Laurie_B, Feb 2026
Beautiful sunset and great crew. Met new friends. Cocktails and appetizers were very good. Smooth sailing and good interactions from crew
Response from Host, Feb 2026
Thank you so much for sharing your experience! We’re so happy to hear you enjoyed the beautiful sunset, tasty cocktails and appetizers, and the smooth, relaxing sail. It’s always a bonus when great conversations and new friendships are part of the evening too!
Our crew loves making sure everyone feels welcome and well taken care of, so it means a lot to hear that stood out to you. We truly appreciate you sailing with us and hope to have you back aboard again soon for another memorable sunset cruise 🌅⛵️
Sandy_R, Feb 2026
This experience was well-planned and well-executed. The crew was friendly and focused and took time to chat with the guests.
Response from Host, Feb 2026
We are so glad you enjoyed your trip. Thank you for the kind feedback and we would love to have you back on deck soon!
Mary_C, Feb 2026
Great cruise for a nice evening. Crew was engaged, polite and professional. Well worth the money spent.
Response from Host, Feb 2026
Thank you so much for the great review!!!
The crew will love to hear you enjoyed your time with them. We would love to have you back aboard soon!
From $89.00
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