Schooner Appledore
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Schooner Appledore
Schooner Appledore II circumnavigated the world on her first journey. She continues to prove her seaworthiness as she makes the twice-a-year journey between Key West and Camden for daily sailing adventures. Appledore Star is the last known Chesapeake Bugeye ever built. This unique shallow draft design allows her to navigate Key West's backcountry with ease on daily eco-tours exploring mangrove islands.

Experience a Key West bucket list experience on one of our historic Schooners. Choose from our award winning Key West Sunset Sail, Key West Windjammer Day Sail, Key West Eco-Tour or start your vacation with our Key West Bloody Mary Sail. Step aboard the Appledore II for a true sailing adventure. This two-masted hand-built wooden schooner calls both Camden, Maine and Key West, Florida home.
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Step aboard the Appledore II for a true sailing adventure. This two-masted hand-built wooden schooner calls both Camden, Maine and Key West, Florida home. During warm summer months enjoy a scenic sail along Maine's magnificent rocky coast. When the weather turns cold, the Appledore II heads south and sails Key West's tropical waters all winter and spring.
Experience sailing on a majestic 2-masted schooner, just like adventurers from the 19th century, while enjoying the luxurious accommodations of a traditional passenger windjammer. The Appledore II is the second in a series of historic schooners commissioned by the Smith family to travel the world. Feel the sense of adventure as the crew hoists the sails.
Soak in the sights while enjoying drinks and appetizers throughout your Key West sunset cruise. Included with your tour is champagne, boutique wine, our famous home-made tropical sangria, ice cold beer, full cocktail bar and soft drinks. A chef's selection of hors d'oeuvres and cocktail shrimp complete your perfect evening.
Our tall ship was hand-built in the same tradition of schooners since the 1700s. This 86' windjammer has circumnavigated the globe. Today the Appledore II gracefully skims into the Atlantic in search of the perfect sunset. Feel the sense of adventure as the crew hoists the sails. Participate in this age-old tradition by helping raise the sails.
Nothing stirs the romantic heart more then the Appledore II's classic wooden hull whispering its way into the seas. The Appledore II - more then a boat, it's a tradition. The Appledore II is a majestic 86' windjammer and the largest of her sister ships, Appledores I, III, IV, and V. She is the last schooner custom built by the Gamage Shipyard.
Reviews (15)
Jaclyn Mitchell
Jaclyn Mitchell
Jan 29, 2022
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Boat is absolutely beautiful, crew is amazing. Sunset sail in Key West was all we could have asked for, she moved gracefully through the water with a crew who knew how to handle her. Hoping we can catch her in main next year!
Penny Crosson
Penny Crosson
Jan 03, 2022
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What a terrific way to spend the day with Russ, Wade and Davon! They made our whole experience one we will treasure in our memories. We were treated as special guests who they wanted to entertain and educate all while letting us relax. They keep the number of guests low so you get just the right amount of attention. We kayaked around a small island while Davon pointed out the birds and tree growth which was very interesting and informative. Then they fed us a fabulous meal! The day could not have been better! I highly recommend this.
Cyndy Porter Laughlin
Cyndy Porter Laughlin
Dec 30, 2021
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We visited Key West with another couple and all had a great time on the Star. Captain Russ, Wade and Davin provided for a fun time exploring Mule Key and just enjoying the water. Thanks guys!
Marya Gwadz
Marya Gwadz
Dec 30, 2021
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We had a great day with Wade, Davin, and the Captain! Davin knows tons about the local environment and marine life and the crew took good care of us. Wade is hilarious and makes the trip a lot of fun. We’ll be back
Saoda Cynthia
Saoda Cynthia
Dec 26, 2021
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It was an hour roundtrip boat cruise at the key west with amazing sunset and shore view! The cruise included unlimited drinks and some snacks. I absolutely enjoyed the trip whole time.
Debbie Rhodes
Debbie Rhodes
Dec 20, 2021
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We had such a great evening on the sunset sail. It did rain on us a bit when returning to the marina but the crew can’t control everything! The appetizers and the drink selections had something for everyone. The captain and crew worked very well together and provided an intimate experience and I have a greater appreciation for sailing, tacking and schooner life. The quietness of being on the water without the hum of engines and appreciating these skilled sailors was amazing! Do this experience!
Justin Davenport
Justin Davenport
Nov 23, 2021
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My wife and I went on a sunset sail for our anniversary and absolutely enjoyed the scenery, drinks, and attentive service of the deck hands and the captain. There's just something different and better than being on a schooner than a catamaran.
Mick Bilger
Mick Bilger
Nov 21, 2021
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Russ, Mario, and Wade were absolutely incredible guides/hosts, as was the adventure itself!! You can always tell when someone loves what they do!! Snorkeling and kayaking was amazing as was the sailing back to the wharf. Truly a perfect day on the water. We will absolutely be return customers and would recommend to anyone visiting Key West.
Thanks boys. See you again soon!
Pattie Rivers
Pattie Rivers
Oct 30, 2021
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We thoroughly enjoyed our sunset cruise aboard the Appledore Star in Key West October 6, 2021. The crew was wonderful, and the bar was full of anything you could want. Then we were served delicious hors d’oeuvres to top it off, ending with a beautiful sunset! Thanks, again!
Meghan Bright Graham
Meghan Bright Graham
Oct 03, 2021
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This was recommended to me, and now after having experienced it today I can recommended it. The crew is so friendly and knowledgeable. 100% worth every penny!
Heather Brown Donahue
Heather Brown Donahue
Sep 29, 2021
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My sister and I sent our parents on a sunset cruise for their anniversary. They had a wonderful time and really enjoyed the conversation with the captain. Their original cruise was rescheduled due to rain, so they were very happy to be able to find another day that was open. Thank you for such a wonderful day for them!
Mark Cone
Mark Cone
Oct 03, 2020
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This was the best Eco Your I have ever been on. Rae and Russ were amazing they gave personal attention to all the guest. Were super helpful, made sure we were safe during our tour. We saw a 6 ft nurse shark, slot of different fish, turtles oh and the kayak trip was cool, we went into the keys and learned about how they form and all the animals that live in them. Book this trip you will not regret it!
Nolan Couture
Nolan Couture
Jul 29, 2020
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My wife and I had a great experience with Schooner Appledore on the Appledore Star. It was our first time in key west and our 10 year anniversary. Of course it was during the COVID stuff but the experience was great. They did everything they could to help with the situation and we even had a lesser passenger cruise which in itself was awesome because it was more personal. Captain Russ and first mate Rea were first rate and would definitely go on this sunset cruise again when in the keys in the future.
Bonnie N.
Bonnie N.
Feb 03, 2020
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They told us we would snorkel by the reef and kayak. We ended up not doing anything because when we stopped to kayak the first group took 45 minutes and by the time they got back the tide have came in and it was too shallow and the kayaking on the second group got stuck so we had to turn around and get back on the ship. The water we swam in while we waited for the first group was mucky and gross. Then we were told we were going to go snorkeling but another ship was there first so the dropped us off behind them and with the tide we swam for over an hour and still never reached the reef. Then they
Richard Cuneo
Richard Cuneo
Jan 07, 2018
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If you're looking for a romantic sailing experience with your loved one, or just a relaxed, friendly atmosphere with the best view of the sunset you can get, you can't beat this boat! We took a sunset sail on Christmas Eve on the larger of the two Appledore schooners. Crew was fantastic and made you feel like your friends took you out on their boat for a sail. They served hors d'oeuvres and had a good selection of wine, beer and liquor which they were not shy to serve. Relaxing and enjoying the sunset with my fiancee', I was very glad we chose to spend a few more dollars on this experience over