1. Schooner Appledore

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Key West, FL

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Schooner Appledore

4.9 (113 reviews)
Open • 9:00 am - 8:00 pm

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Sunset
Chad A.

Melisssa greeted us before departure with a friendly smile at Appledore. There are a number of charters that sail out of the same area, and immediately you start to realize that you chose the fight one based off of how organized Appledore is and how well they communicate to guests. Boat crew (Captain Joe, Jack, and Kristina) are super professional and know their craft and hospitality. Everyone felt safe and greatly enjoyed the experience. Small snacks were tasty and served along with drinks, and this schooner was family friendly yet more adult orientated. Will come back next year.

Rosie M.

Had an incredible sunset experience thanks to Joe and Christina! They did a great job covering all of the safety features, and then their knowledge of the vessel and clear care for it put me even further at ease. I really enjoyed getting to watch their teamwork and communication in the actually sailing of the schooner. Yummy hors d'oeuvres and refreshing drinks. Definitely a highlight of my trip to the keys!

Birthday girls

Emerson and Christina made our evening SPECTACULAR! We learned a lot about the different boats around us. How old our ship was and why it was different from the others. Smart, fun, entertaining.food was tasty and cocktails. We enjoyed the small group instead of a large crowed ship. We would recommend this boat for a very relaxing voyage with some fun and tasty treats.

Captain Will

Took a sunset cruise on this gorgeous and fully functional sailing vessel. Other than motoring in and out, we sailed the entire time. Capt Will and Capt Kelly did a great job with their fun crew. Excellent drinks and apps. Would highly recommended. Was all we hoped for and more!

Jude B.

What a fabulous sail off Key West in the most beautiful and historic schooner. Sailing into the gulf waters for Sunset, we boarded 4:20, the Great crew was friendly and attentive, Captain Luke, mate's Josh and Sean were the best!! The guys served us drinks, fast, often & unlimited. The appetizers were petite, cute & tasty. A Caprese pick, tiny toast with half teaspoon of fish spread, 3 shrimp in a cup, and a bite size key lime pie. All were good. The winds were good tonight to carry us out for an hour or so and then hour back. So peaceful, and 80° sunshine, winds and salty sea offered a few splashes just a wonderful experience! (You may get a bit wet, so leave your leather bags in the car, some got wet). This is a knowledge crew so ask them questions about the boat or sailing they are nice to engage. It was a beautiful 2 hour adventure on the seas before returning back to dock at 6:40 in the Historic Seaport.

View from the docks
Rick C.

Great crew, great location and great price for 2 hrs in the bay. This company has a franchise in Ley west and in Maine. Would recommend both.

Sunset Cruise
Felix P.

Great crew and great company. We really enjoyed both chatters we have now been on with them. I highly recommend this crew and this boat!! We will be back!

Alison L.

We had a great time on the sunset sail. Awesome experience. The captain and first mate were top notch. They were fun to interact with and quick to grab us a drink.

Dee M.

Great experience Unlimited drinks Crew very friendly Participant volunteers help to hoist the sails.

Pat B.

This is our second trip out with these folks in over a number of years and they remain consistently great. The trip we went on was 2 hrs long. It's fun, informative and the crew is very attentive. They serve alcoholic and non alcoholic beverages while sailing. They involve the customers in the fun. Tonight we were gifted with a bit of sunset color, a peaceful sail and dolphins jumping along side us.

K R.

The Schooner Appledore is a fantastic treasure that offers the best sunset cruise around! It is a peaceful setting with a fun loving and extremely experienced Captain (Gil) who has sailed the waters of the keys and beyond. The Appledore is the best kept secret because it is a true tradition for the keys of times gone by and for those who crave to experience the sunset as nature would have it. The sail is calm, relaxing, quiet, offers the ability to hear the water and offers all guests true serenity. The crew consisted of Jack and Andy, two young and impressive mates with mature knowledge of the sails. These young men make it fun by asking the guests on board to assist with the sails going up as the ship departs the marina. They serve delicious appetizers and a wide selection of cocktails as well as water and soda. The best part was when we ventured away from the noisy giant catamarans full of thumping music and packed groups of people and simply sailed along the horizon as the breathtaking sun dipped into the water. The Appledore is a true pirates chest of value and she allows Mother Nature to propel her through the waters as if you were floating on a cloud. The ticket price, the time on the water, the drinks and food served are a fantastic value. The crew deserves the best tip!! We also stayed out longer than the other vessels taking advantage of the sunset after glow which made it even more special. Thanks Captain Gil for an unforgettable experience.

Schooner Appledore Sunset

We really enjoyed our sunset cruise on the Appledore II in Key West. If you are looking for a smaller/low-key sunset cruise this is it. Great opportunity to meet the crew (Jared & Thomas) and hear more about key west, plus Thomas' rum punch was delicious!

Hanging on the deck
Jazmyne S.

Amazing time sailing with captain Jared, Dakota and Levi. We booked a private sail with 18 people for my husband's 40th birthday and had a blast. Plenty of food and drinks to go around. Beautiful sunset views and great staff made it something we'll remember for years to come.

Sunset off Mallory on the schooner.

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3 years ago

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2 years ago

Jack and Jared were both so awesome and we had a blast! Highly recommend! The snacks and drinks were great too!

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2 years ago

Highly recommend. Owner is very accommodating and rhetorical crew was great. First class outfit and great boat.

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5 years ago

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2 years ago

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2 years ago

Amazing sail! The crew of brothers were great and delivered awesome wind and weather!

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6 years ago

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3 years ago

Absolutely recommend the Sunset cruise! Captain Jared, crew Mario and Renee are top notch. You will not be disappointed!

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4 years ago

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3 years ago

Highly recommend the Bugeye Backcountry Eco Tour...a very professional, positive experience....go, you'll be happy you did

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3 years ago

Excellent boat! Intimate setting but laidback. Captain Mareson (Mario) and mates Bradley and Jamie are top notch!

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6 years ago

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Page 2 of 3

Ask the Community - Schooner Appledore

Review Highlights - Schooner Appledore

“The crew consisted of Jack and Andy, two young and impressive mates with mature knowledge of the sails.”

Mentioned in 64 reviews

Read more highlights

Floridays - The golden hour on the Floidays

Floridays

(133 reviews)

We wanted to do some snorkeling and found Floridays on the TripAdvisor website. We thought the…read moreprice was reasonable for the amount of time (3 hours, total with 1 hour of snorkeling). We are staying in Islamorada, so it took us just about two hours to drive to Key West. If you're not staying in Key West, one must take the driving time into consideration, as traffic can travel pretty slowly sometimes... Our captain was Lanier and Parker was first mate. They both did a great job of taking care of us. Lanier offered really helpful information and was great at answering our questions as he steered us to the reef. Parker was really nice and made us feel welcome with conversation and drinks. Once we got to the reef, the snorkeling was really great! I don't have very good eyesight, so I bought some prescription goggles and I was not disappointed. I saw many different kinds of colorful fish, including some that liked to swim pretty close to me. It was a bit windy, so there were some waves that eventually had me feeling slightly queasy, but I was still able to snorkel for 40 - 50 minutes. Unfortunately, my wife actually did get seasick and Parker was super sweet to aid her and a handful of the other guests who got seasick. Her ice on the neck trick seemed to really help us "land lubbers" :) If you're in Key West and want to see some beautiful fish, I would definitely go with Floridays!

My fiancé and I did the sunset sail with drinks included and had a GREAT time. It was a lovely…read moresail. We made some new friends. The crew, Owen and Jared were AMAZINNNG. Both of them were attentive and friendly. They were working their butts off to make sure we had a good time. Thank you Owen and Jared for an amazing sail!

Schooner Appledore - boatcharters - Updated October 2026

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