There's something about stepping aboard the Appledore Schooner that hits you square in the chest in a good way. The wood creaks just enough to whisper stories, the sails stretch like they've seen a hundred lifetimes, and even knowing it's a polished replica, it still feels like you've signed up for a voyage out of another century. The breeze rolls in warm and salty, drinks are flowing, food's dialed in, and the crew runs a tight ship without killing the charm. It's not just a boat ride it's a floating time machine with just enough modern comfort to keep you from questioning your life choices. Now toss in my crew a full-blown cast of characters that could rival The Hangover. One guy shows up dressed like a budget pirate, fully committed. Another thinks every moment is an opportunity for a prank. Then you've got the intellectual who knows everything, the guy who drinks like it's a competitive sport, the jokester, the snob and me, somewhere in the middle just trying to keep the ship from turning into a crime scene. I swear, the energy alone had "we're getting kicked off" written all over it before we even left the dock. And sure enough, chaos found us. A "harmless" prank turned into a domino effect one bumped shoulder, one spilled drink, one very offended passenger, and suddenly we're apologizing while trying not to laugh. At one point, our drunk friend got a little too bold near the edge, and let's just say there was a moment where we all collectively realized how quickly a sunset cruise could turn into a rescue mission. Words were exchanged, tensions flared, and for a split second it looked like fists might fly but somehow, like all great misadventures, it smoothed itself out into laughter, stories, and another round of drinks. End of the day? Absolutely worth it. Get on that boat, bring your people, and don't just take the ride make it a story you'll be telling for years. read more

Schooner Appledore - Boat Charters Near Me - Key West, Florida

Great Sunset sail with Captain Joe and first mate Vitale. Very professional and courteous Peaceful, with drinks and appetizers Pick this one read more

We stumbled onto this excursion while vacationing in Key West. There were a few different options, but this one checked all our boxes. I wanted something family‑friendly, not too long, not too pricey, and ideally on a unique boat. We also did not need the extra "whistles" like open bar, DJs, sunset cruise, or crowded boats. Appledore had everything we were looking for and it did not disappoint. Check‑in was a little confusing, but just follow the signs for the Schooner Appledore II and you'll be fine. There are tons of restaurants and bars nearby, so go early, get your bearings, and treat yourself to snacks, lunch, or a drink. During our trip, we even saw one group miss the tour because part of their party didn't make it to the boat in time... so don't be that group. The boat itself is a replica 18th‑century schooner, and it's immaculately maintained. The three‑person crew (Captain Josh, Christine, and Ryan) ran the show. They were knowledgeable, friendly, and kept everyone's drinks filled--basically the dream team. They also asked for volunteers to help hoist the sails, and my two youngest jumped in like they'd been training for this moment their whole lives. We chatted with Christine the most, and she explained different sailing terms and parts of the boat, making us feel like honorary sailors. The sailboat takes a few minutes to set up, then heads out for about 45 minutes before turning around and cruising back to the docks. The whole experience lasts about two hours and is absolutely worth it. read more

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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. read more

Schooner Appledore - Sunset - Boat Charters Near Me - Key West, Florida

Wonderful experience with Captain Josh and Ryan and Christina as crew. We were celebrating our wedding anniversary and our sunset cruise on this beautiful schooner helped mark our special occasion. Everything from the communication to the safety briefing to the refreshments and the conversations were great. Highly recommended! read more

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! read more

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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! read more

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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. read more

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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. read more

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My daughter and I booked last minute snorkel, kayak, and sail tour. Captain Marisol and First Mate Vitale were super knowledgeable and professional. The lunch was amazing and the "house" recipe pain killer is a must. Perfect day on the water. read more

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. read more

Schooner Appledore - View from the docks - Boat Charters Near Me - Key West, Florida

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Captains Joe and Christine were very professional and welcoming. Their attention to service was top notch. The actual boat ride was very relaxing and watching the sun set was the icing on the cake read more

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! read more

Schooner Appledore - Sunset Cruise - Boat Charters Near Me - Key West, Florida

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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. read more

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

Schooner Appledore - Boat Charters Near Me - Key West, Florida

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. read more

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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. read more

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We had a wonderful time aboard the Appledore! The crew is amazing and the captain was great. Highly recommend this company as it is small group sailing. Everyone was very accommodating. We hit rough water and high winds and had to turn back for safety reasons, but we kept sailing around in calming waters. Had a really nice afternoon adventure. read more

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! read more

Schooner Appledore - Schooner Appledore Sunset - Boat Charters Near Me - Key West, Florida

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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. read more

Schooner Appledore - Hanging on the deck - Boat Charters Near Me - Key West, Florida

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Beautiful sail! Memorable way to see a KW sunset. Capt Joe and first mate Carley are a great team, serving up generous bevs and tasty apps. They seem genuinely happy to get ppl out on the water. Highly recommend this champagne cruise! read more

Captain Joe was informative and professional, deck, and Michael had to do all the manual labor! But he also served excellent cocktails and hors d'oeuvres. A great trip for everyone involved, definitely recommend. read more

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Fantastic time on the Appledore Star! Captain Jared and First Mate Thomas were outstanding! We've done numerous sunset tours over the years, with different companies and boats, and this was by far our favorite. read more

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The trip was fantastic. The view, the wind and the crew could not have been more pleasant. Russ and Wade went above and beyond but Jason attempted to ensure every need was met. Thanks. read more

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We loved our sunset cruise with Captain Joe & Dakota. 2 hours is the perfect amount of time. The drinks were flowing & the appetizers were delicious. It's not a ton of food so definitely plan to eat dinner before or right after. We felt so relaxed & enjoyed this magical sunset. The guys don't talk about history or anything and we liked that so we could just really relax and take in all the sights. Highly recommend! read more

Schooner Appledore - Sunset Cruise on the Schooner Appledore - Boat Charters Near Me - Key West, Florida

Pablo, Michael and Sean were awesome! A perfect cruise to go out with and enjoy camaraderie and the environment! Guaranteed to have a great time read more

It was a great sunset cruise! Enjoyed being on a schooner and watching the sunset. The crew was amazing and we enjoyed the drinks and snacks. Will definitely do it again. read more

Beautiful boat, excellent service & such a fun evening. Brad, Ray, Victoria, etc were exceptional. We had a great time. The sunset cruise did not disappoint !! read more

Had an amazing sunset sailing with the crew of the Appledore. All the crew was fantastic and the boat was wonderful. My only complaint is that I was hoping for a more peaceful sunset sail but instead seemed always passing catamarans blaring music and we all zig zagged essentially the same path. It would have a been nice to get out away from the other boats more. Definitely did not ruin the experience though. Would highly recommend! read more

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Great time was had by all. The crew, the cocktails and the food was great. At a maximum of 22 passengers this was most relaxing. read more

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Great sunset cruise! Captain Joe and his crew were fantastic, very knowledgeable and helpful!

My wife and I did the 5 hour trip that included the snorkeling, kayak tour, lunch and beverages. Beverages was anything from home made sangria, coke and rum, soda, champagne and water. Captain Joe and first mate Bradley did a fantastic job of showing us a good time during the sail. We saw some dolphins during the sail plus we saw a turtle, stingray and miniature crabs as we kayaked through the mangroves. The schooner ship is about a 40 year old ship about 60' feet long and sails very smoothly. Thank you Joe and Bradley for the professionalism and wonderful time you showed us all. read more

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This sunset sail was a mother fucking spectacle. Likely the best part of my Key West adventure. Absolutely unforgettable. The crew was so welcoming and it was so enjoyable to watch them work. I felt like Moana. The snacks were amazing and so were the drinks. The guys were super attentive while also working hard to navigate. There were only 8 people on our sail which made it so much more intimate. Make sure you check out the cabin underneath. The boat is a true work of art. We got to see a beautiful sunset and a spectacular full moon rise. What a glorious end to our trip. read more

Schooner Appledore - Boat Charters Near Me - Key West, Florida

Nice boat, GREAT Crew - we had a fantastic time getting out on the water with this group! Mike and Capt Joe led a safe and fun day for all - Highly recommend! read more

Sunset Champagne Cruise. The crew was professional and friendly, views were amazing. Snacks and wine were plentiful, There was a mid-cruise change in the weather that the crew expertly handled. Small group size is wonderful, Highly recommended read more

Schooner Appledore - Sunset from the Schooner - Boat Charters Near Me - Key West, Florida

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Affordable, relaxing, and a fun time. This crew was awesome. They work hard so you don't have to do anything but enjoy your cocktail and the sunset. Truly a fun experience. Great for the whole family. There were kids, bachelorette party, and even a dog on board. read more

Schooner Appledore - Jenna - hard at work! - Boat Charters Near Me - Key West, Florida

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We had a wonderful sunset sail with Russ, Mario and Wayne tonight! We were a little skeptical with the cloud cover, but we ended up having a beautiful sunset. The crew is very personable, always keeping our drinks full and our bellies satisfied (but leaving enough room to go for dinner after). read more

Schooner Appledore - Boat Charters Near Me - Key West, Florida

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Excellent crew that were professional informative and very attentive. We took the sunset, cruise and reserved our space via the concierge right near the dock as opposed to doing it online. The snacks were yummy . The drinks both you paid for or that were free were very good. It rained a little and the sunset was muted but still had a wonderful time. read more

We has a fabulous experience on the Appledore sailboat. A few us have enjoyed previous sun set cruises on the Appledore so our expectations were high. They did not disappoint. Will do it again!​ read more

Great experience all around! Pablo was friendly, as was the whole crew, and very efficient with safety. Loved the history of the boat and happy we decided last minute to jump on! read more

Schooner Appledore - Sunset - Boat Charters Near Me - Key West, Florida

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