The sunset cruise aboard the Appledore was fantastic! Russ, Isaac, and Laura provided a great experience and some good stories as well. We got to witness a competition between the Appledore and another schooner setting sail. Our first mate Isaac whipped the other bunch handily. I'm sure both crews had some good back and forth about that later in the evening. It's a treat to get a crew that is professional and fun at the same time. J Finley read more

My husband and I had a great time on the Appledore for an ecotour of kayaking, snorkeling, lunch, and plenty of drinks. Captain Russ led the crew of Isaac and Maddie, all of whom were friendly and helpful guides as we made our way over to Archer Key. During our kayaking, we saw several species of birds and a few sea turtles, and while snorkeling, we saw a variety of coral, sponges, and fish. Lunch was great (fried chicken, macaroni salad, peel and eat shrimp, and cold cut sandwiches) and the crew kept us from ever having our beer or sangria run dry. Everyone on the trip was friendly, relaxed, and looking to have a good time. This made for such a fun experience while on our Key West vacation, and my husband and and I would recommend it for anyone looking to get out on the water without a huge crowd of 50+ people. read more

Crew was great. Very willing to answer all questions. Took family photos. Trip was lovely. Highly recommend

Best trip in the Key West. Isaac, Madi, Russ did a wonderful job. Highly recommend you do not miss this boat ride.

Captain Russ, Wade, and Mario took excellent care of our family of 4! The kayak tour was interesting and you could hear Wade's passion for sharing his knowledge of the mangroves with us. read more

We had a wonderful sunset cruise with the crew on the Appledore! Bradley and Mario were awesome! We've gone on this cruise twice and would choose it over the crowded, big boats any time! read more

We decided on the Schooner Appledore for our sunset sail and we were not disappointed at all. The crew (Mario, Russ, and Bradley) were all super informative and helpful. By far one of my favorite experiences of our trip and would not hesitate to book another trip with them. read more

Great experience! Wonderful Captain and Crew! We had a beautiful day kayaking and snorkeling, nice lunch, fun day. Highly recommend!

THE BEST $$$$ spent in Key West! Can't imagine coming and not taking the cruise on schooner Appledore Star. Captain Kate and crew ensured each of us had a fantastic evening Not to be missed!!! read more

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

We live in Key West and try to go out for a sunset sail once a month on the Appledore. Captain Mathew and his crew are skilled in both seamanship and hospitality. My wife and I often engage visitors to Key West in conversation about their trip to this island paradise. Universally, they give their sail aboard the Appledore their highest ratings. read more

Joe, Gus and especially DREW!!! Thank you for providing my husband and I with a Fabulous sunset cruise! We went for our first time- we've been visiting Key West since 1983! We will definitely be back! Drew you did a great job juggling all those delicious appetizers! read more

Mind blowing sailing experience at Appledore II ! The Schuner Appledore 2 is built in 1978 according to our sailor.It was gorgeous to start with. Just a handful of folks and sailor crew of 3 & we all had a fabulous sunset sail. The crew was amazing, very friendly and attentive. We were served with delicious cheese, crackers and fruits and unlimited drinks. The best part was to sail in the middle of the high tides in the Gulf of Mexico. The experience was a perfect amalgamation of adventure, fun and beauty. I would recommend this sail to everybody who wants to experience beautiful sunset along with fun sail. read more

Two hours of sailing around outside of Key West Bight is one of the nicest ways to spend a sunny, windy day. The ship is lovely, the crew friendly (one of them was even a Conch--you don't meet many people actually born and raised here!), the selection of beverages good. They even had home-made sangria in the drinks locker, which was very nice. And there was the bonus of a trio of musicians from Canada playing sea shanties (it was like being at the Lower Deck in Halifax!). Reservations required! A year later, we did the sunset sail. Just as great as the day sail and a real deal compared to other sailing sunset cruises. No band this time, but we had a blast with the other passengers. Sunset was a dud, but there's nothing the crew could do about that except pour more drinks! read more

This was an experience that four of us, to 65-year-old and two mid-30-year-olds did towards the end of our trip in Key West. Overall, it was a surprisingly wonderful experience. I say surprising because I am usually a fan of more modern ships and/or means of transportation. In this case however, it was wonderful to have the power of the wind to move us. The ride was much longer than expected, which was good, and the experience was better than I thought it was going to be. The crew was very professional, funny and interactive. The service they provided by way of serving drinks and conversation was far beyond anything we experienced on land in Key West. Of particular note is Jan, who as well as being professional, courteous and funny, bears a striking resemblance to Bradley Cooper. The only downside to the experience was the amount of appetizers provided. We were quite hungry upon our boarding and the cheese and fruit platter may have sufficed, so long as some kids didn't pour the trade as they did. But the experience of this excursion shouldn't be judged on poor parenting. in short, If you will be in Key West and can spare two hours or more, I highly recommend doing this. You will get a much better viewing of the sunset and the island itself, and the service quality will exceed anything you get on land. Tip these guys well read more

Our favorite schooner in a town full of them. The Appledore crew of Chris the Captain, and his two assistants, Cory and the other deckhand (whose name escapes me) were a wonderfully accomplished group who served wonderful food (great shrimp, lovely key lime tarts, as well as cheese burger sliders, and simply one delicious thing after another -- due as I understand to the Sebago catering crew) and were generous in all ways to me. I am in a wheelchair and they lifted me on and off the boat with gentility and ease, and gave me a blanket when I said I was cold after the sun went down. Chris's sailing was spectacular -- the deckhands kept the ropes moving smoothly to make our sails bellow out full of the wind; we tacked back and forth in the channel to get one-after-another beautiful view of the sunset and the other boats on the water with us. What a lovely Christmas night! We were with a lovely group of adults on the cruise: no noisy drunks, no irritating music, just the sound of the water moving against the wooden boat. I'd recommend this schooner to anyone who appreciates the finer experiences in Key West, a town too often represented by its worst features. read more

Outstanding. The best sunset cruise ever taken...and I've taken many. Capt Russ, Issac and Mattie were outstanding. Quality of food and beverage excellent. We saw the sun sink from all angles. These folks did it right! read more

This is the real deal, a traditional sailing schooner with all its grace and charm. The sunset sail we were on was perfection. The crew knows their ship and sails her falsely. They involved the passenger if they wanted to help raise the sails, or take a turn at the helm. Our weather and wind was just right for a marvelous time. read more

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

My wife and I decided to get this booked as a Christmas present for eight of us going to key west. We were not disappointed and neither was our family! It started off just a hair rocky as we were not exactly clear on the check in process. Partly my fault for not realizing the address was to a building on the street a half a block away. We were early so it was not a big deal. We just went down to the office to check in and then got on the ship. It maybe could be a little more clear considering we were just tourists and not from the area. I recommend googling the address to make sure you're in the right spot. I did not and that was my fault. Onto the ship! The captain and crew were very professional and informative. I was blown away at their knowledge of the ship and it's history. This is not just a tourist ship and does sail up to Maine and back so check with trip advisor or Sebago for seasonal availability. This was a huge plus for me as it added to the stories and history of the ship and it's crew. The captain was so nice he even turned the ship around when someone's hat blew off. Maybe a little showboating (pun intended) but it was amazing to see this in action. The food was good and plentiful and so were the drinks. The crew did the serving and it was the perfect opportunity to ask them questions and they are happy to answer them. The trip was even interactive as they asked for volunteers to help raise the sails. Of course my mother in law jumped on the opportunity and I got great video of it. The entire trip was great and the views are beyond amazing. This is a definite must for anyone vacationing in the keys. read more

Great Evening Cruise! We loved the boat, the crew, the food, the drink. Would absolutely go again (if we had time!!!). Great value too, purchased through Trip Advisor, which was actually the best price I could find (59/p). It is a smaller boat so there were no hoards of people fighting for space....plenty of room to walk around, sit, move to another seat. Crew was fast with the drinks and the caprese skewers, stuffed peppers, small burgers were fun and delicious. All crew knew everything about the boat and we had a great time! read more

Great sunset cruise; would highly recommend. Beer, wine & champagne are served along with light hors d'oeuvres. The cruise takes you out into the harbor in front of Mallory Square where you get the most spectacular views of the sunset. The crew of the Appledore are friendly & attentive and happy to answer questions & provide excellent service. read more

This was our second trip on the Appledore 2. First time was out of Camden Maine. We saw the ship sitting there and had to try it again in Key West. Even better this time. All you can drink Sangria!!!! Crew was A+ here. Throw em a good tip! read more

The crew of the Appledore were fantastic. We went as a relatively large group (14 people) for a joint birthday party and the weather was perfect, bar service fantastic and the fresh pineapple delicious! It's about a two hour boat ride and, if you like, you can help raise the sails when you get going! Ask any question you like, the crew was easy going, made us laugh and they were a delight to be around. It is not a fancy party boat with dancing and music, but that means it's not as crowded or loud. We had a blast and I'd do it again in a heartbeat. read more

Went on the 11 am Bloody Mary cruise. They had a full stocked bar. Staff was all amazing. Captain Chris is so passionate about the boat. Loved hearing it's story. Taylor and Cory were always ready to help and all were very personable. A great way to spend the afternoon in Key West! read more

As you all know if you have read any of my reviews, Ive recently relocated permanently to Key West, Fl. After settling in, getting to know my way around, (by bike being my husband has not yet arrived here permanently with our vehicles) I did a little online research because, after seeing these lovely tall sailing ships, the schooners, along the coast line onn my morning bike rides, I made it my first priority to experience. I chose the Appledore Schooner. Built in 1978, it has been around the world so has character. It is totally constructed of wood and has a feel to it as if you are actually traveling back thru time. The young crew was FANTASTIC. First and foremost, very capable. Amiable. Witty, and accomodating. Being the crew consisted of only 3, we were encouraged to help with the sails etc. I jumped at the chance and loved it. (they do recommend you bring a hat, a towel, and sunscreen. I didnt use any...:) I DID put on a long sleeve t shirt when returning to dock being it truly was s windy day. I did go prepared as they suggested. They served beverages ( adult and non adult) and seemed to enjoy the 2 hr trip out into beautiful teal waters as much as the 12 or so passengers sailing with them that day. Being I was alone, I sat up front and just savored the breeze, the beauty, and my good fortune to be spending my day, in my new hometown, doing something so lovely This particular vessel does return to Maine May 31st for the summer, so I plan to sail one more time with them before they leave. My puppy is also welcome to sail along. Thank you crew of Appledore! read more

My husband had been so disappointed by a different company's "sunset sail" that didn't even involve sailing (they put up one of the sails but ran the ship's motor the entire trip), but Appledore was a dream come true for him. The staff does a great job of telling guests about the schooner's history, allowing guests to help man the ropes and the wheel and making guests feel one-hundred-percent at home with the friendliest approach. We enjoyed a lovely tray of fresh fruits, crackers and cheeses and tasty sangrias. On our trip, most of the patrons were return guests who knew all the crew by name and made a point of going out daily on the Appledore during their trips to Key West. You couldn't find a friendlier staff ... be sure to ask them about their best stories from their sailing adventures! I'm brain-farting on the names of the staff members who really wowed us but for sure have great things to say about Captain Kate and Jan. Thanks for the tremendous time! read more

Schooner Appledore - Captain Kate hands the wheel to my husband. He was thrilled! - Boat Charters Near Me - Key West, Florida

Wonderful sunset sail on an old windjammer. Light appetizers wine or beer but the best was the crew!

We took the sunset cruise on the Appledore II, and found it to be an excellent experience. The boat was a beautiful authentic sailing vessel which made the trip worthwhile. Captain Chris and his crew taught us about both the boat and sailing in general. If you want an authentic experience, book your cruise on the Appledore II through Sebago. read more

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

I have been to Key West many time over the past 35 years and sailing on the Appeldore was one of the best experiences I have had! Great crew, great time, great people! read more

Most amazing sunset cruise ever!! Captain Chris and deckhand Parker made the view even more amazing!

Just had the experience of a lifetime on this amazing excursion. It was a rare cold, breezy late afternoon in January in Key West, but our group wanted to experience a Key West sunset. The very knowledgeable captain and crew on this unique, authentic 1930's schooner made it an exceptional rewarding time. They answered all of our questions about the beautiful ship and made it very educational. Oh yeah....the delicious appetizers, ample libations and best ever home made sangria didn't disappoint. And the sunset stole the show...the brilliant colors are burned into my memory. This is a must do! read more

The sunset sail with the Appledore is offered through Sebago watersports and is a fun ship to go on! Everything from the check-in to getting settled on the boat is done very professionally and we never felt rushed. Passengers got the chance to help out with the raising of the sails to help us get under way faster, always fun to watch! Beverages and food provided by the crew were nice and light. We also got to interact with another ship out on the water, the Jolly Roger pirate ship, cannons galore ;o) Sunset that evening was nothing too spectacular, it was a bit hazy at the horizon. On the way back in, we had a dolphin playing in our bow that we were able to watch and enjoy. All in all, a fun trip, much better to be on a traditional schooner than on one of the catamaran party ships with the loud music. A bit more of a cozy experience with this charter boat, I would definitely go again. read more

Awesome ship and really fantastic crew! 13 of us went out for a memorial sail; everyone was very respectful, fun and friendly. It is very evident that Captain Chris and crew know and love the Appledore. Can't recommend it enough! read more

Beautiful ship. Informative crew. 2 hours in Gulf and atlantic. And of course a beautiful key west sunset. Well worth the price.