Lovely sail along the Key West Coast! We had a wonderful time and had great service (super friendly crew) from Milo, Chelsea, Dan, Brad (or Brian...sorry). Anyway they were great! We will definitely go again! read more

Classic Harbor Line Key West - Boat Charters Near Me - Key West, Florida

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We went on the stargazing sail last night (3/12/26) and it was just really so great! We have lived, six months each year, on Key West for 10 years, and never heard of it until last week & we thoroughly enjoyed it, very glad we went! Often feel silly being pseudo residents (elsewhere in FL otherwise), doing touristy things, but we are always willing to try something new, especially if it involves boating! The crew was wonderful, and Astronomer Kevin is an incredibly smart man, who put on a great presentation. Literally perfect sailing conditions, comfortable boat & all around super experience. Will recommend this to our many, many guests and local friends. Kudos to your staff! read more

Classic Harbor Line Key West - Boat Charters Near Me - Key West, Florida

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Loved the sunset sail. It was so relaxing and well organized. Dan shared stories about the history of Key West that were super interesting. The food was adequate and I was impressed with the drinks- the servers/ sailors kept them coming and they were not stingy at all. Honestly could not think of any improvements. Highly recommend. read more

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We loved our sail. It was fast, faster than all the other sailboats out there. The snacks and drinks were excellent, and the crew was outstanding. We really enjoyed watching them raise and lower the sails. read more

Loved it!!! So fun. Milo was excellent. We celebrated his 19th birthday the day after our sail. read more

Classic Harbor Line Key West - Piloting pics - Boat Charters Near Me - Key West, Florida

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Dan took awesome care of us, and Ray was an amazing Captain. Had the best time ever. read more

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Beautiful sunset sale on a really nice hundred 5 ft yacht with hors d'oeuvres and wine

It was a beautiful night for a sail with Janet, Jane, Mary, and Chelsea! Highly recommend this experience for a unique way to experience Key West from the sea. read more

Really Fun. Great Crew. Great Snacks and Beverages. Highly recommend. Very comfortable ship and we were able to see a gorgeous sunset.

Everything went well. The captain was fun. The crew was amazing. The weather was fantastic. The waves were high and made the trip exciting. A few of us in the front of the boat got a bath, but it was all part of the adventure. I highly recommend this to anybody who likes water and sailing even if you don't like sailing it was fun. read more

Incredible experience on board America 2.0! The Schooner was immaculate, the crew was amazing, reservations & communications were excellent and the sunset views were unbeatable...Had several visits from a large pod of playful dolphins right around sunset that were very interested in our group of sailors! Thanks to Captain Janet and her crew-extremely attentive to the guests in between managing the rigging and sails-they were working extremely hard and you could tell were very professional and experienced mariners...don't miss this experience if you are in Key West!! read more

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This was the perfect Key West sunset sail. The boat is gorgeous and has modern underpinnings. She is built by Scarrano boat builders in Albany NY, and she sails like a dream. We sailed past the traditional schooners like they were aground! Captain Janet had excellent skills, and a welcoming personality. The entire crew was friendly, the food and drinks were wonderful, and our entire group oulld not have been happier. If you are a sailor, this is the boat, and crew, for you! read more

A really awesome team here. We chartered a private sale for a company event and the whole group was beyond happy with the trip. Captain Tom and the crew were polite, informative and so nice to everyone. We all enjoyed the boat with plenty of room, were served drink and snacks all out on sea. Highly recommend. read more

This was a fabulous sunset sail! The captain was very nice and professional. The staff did a great job serving us cocktails and appetizers. They were all very attentive. The sailboat was beautiful and it was a perfect evening. Thank you for a great experience! read more

Once again, a 5+ star experience! The captain and crew are amazing! We left on time, our glasses were frequently topped off, 3 rounds of snacks delivered all while they sailed this beautiful America 2.0. Included with the base ticket: beer, wine, water and soda. Each had several options. As for snacks, round 1 arrived with veggies and ranch dip. Round 2 was a lovely cheese and cracker plate. Round 3 were fresh shrimp and cocktail sauce. Each guest got their own plate. If you want, you can purchase cocktails on board. There are also 2 bathrooms. Of course the view of the water is breathtaking and seeing the sunset's brilliant colors set is simply amazing. Purchasing the tickets online is easy. There is a tip bucket at the end of the cruise for you to reward this hard working crew. Totally recommend. read more

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Had a Christmas sunset cruise and it was great! The captain and crew were very attentive and knowledgeable. We are repeat offenders! I can't recall how many trips we have been on. We even had our reception after our wedding on America 2.0. I highly recommend them read more

We appreciate the exceptional sailing experience you provided. Milo and Mary demonstrated outstanding care for everyone on board. The evening was truly unforgettable. -- in Key West. read more

Ever since I had a sailboat I was intrigued by schooners. Learned a lot on Classic Harbor Line. Fun watching them hoist sails, jibing, and dropping sails. I was especially impressed by the crew working as a team to provide us a fun experience. Thanks to the crew Rae, Jade, Dan, and Bible. As a professor at a woman's college for over 30 years it was especially rewarding to see two women as the bosses. Way to go! read more

Nice cruise. Only issues were no on at ticket gate ate time we were told to be there and didn't start boarding until departure time

Captain Janet was a delight and outstandingly competent. Her crew was able and personable as well as knowledgeable about the vessel and surrounding waters. Don't miss an opportunity to sail aboard this pristine and well equipped schooner. read more

This is a must-do! Had a great, great time! The water was calm, the weather was great, the sunset was beautiful. Pleasantly surprised by the food selection (meat, cheese, veggies) and a nice variety of drinks - both alcohol & non-alcohol. The boat is beautiful. And the crew...they were TERRIFIC. Captain Janet, Heather, Lexie, and Dan - GREAT crew! Friendly, personable, service-oriented, and professional. Thank you Captain Janet for giving me the opportunity to steer - what a great experience! What a great memory! Next time you're in Key West be sure to take the sunset cruise with these guys - highly recommend it. read more

We had the best experience aboard "The America 2.0" from beginning to end. The staff were all welcoming, professional and very good at what they do. Mother Nature also played a part by presenting the most beautiful sunset. There is something magical about Key West Sunsets. If you're looking for a sunset cruise don't hesitate on choosing this one. Thank you Tom for making it possible! read more

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Beautiful day sailing on the America 2.0. Captain and crew were flawless in sailing the schooner, as well as being great hosts. We enjoyed a wonderful cruise, and will do it again! read more

From the start this excursion was fantastic. Heather and Ray answered questions. Was very accommodating and had lots of great photos. Highly recommend!! read more

Quiet, plenty of room, great sailing. Chelsey and Rae were so efficient that htey made the hard work look easy. Very informative and engaging. Professiomals, really. Day sail is a great deal. read more

This is a fabulous experience. We've been taking a "sail' on America 2.0 every December for about 10 years. Always a delight! The crew, Janet, Jade, and Dan, was very attentive, informative, and personable. What made this sail standout was the weather. Strong winds made for an exciting experience reminiscent when we used to sail our own very small craft. It was a real treat in every way! read more

Absolutely our favorite part of the whole trip! Amazing crew! They were so kind and patient. They served us food and drinks. I loved that it was quiet, just the water and the boat. Others going by had loud music and this was the opposite. So peaceful! We watched the sunset and really enjoyed the whole time we were out on the water. They're great at following COVID protocol too!! Side note: it departs from an area that has a couple of shops and restaurants and a public bathroom. Just a helpful tip! #BryYelps I went on my first boat! It was amazing. They let me walk around a little and I liked watching them put up the sails. I got a little bored and tired so mom put me in the carrier. The sunset was pretty. (One year old yelper) read more

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Thank you so much for a wonderful experience!! The ship is beautiful and clean. The staff were knowledgeable , friendly and very good at their job. Plus it was very safe. It was the best way to see the Florida Keys sunset. Which is one of the best in the world. The appetizers were surprisingly delicious too. read more

The best sailboat. The fastest sailboat in the harbor. The best crew. It's the schooner you see in every sunset pic. The Captain will let you steet for a bit for pics. If you only do one sunset cruise in Key West this is the one to do. We've been aboard about 6 times including twice in one week. read more

My husband and I went on an afternoon cruise on a beautiful sunny day with pretty calm seas. The crew was wonderful - very friendly, sharing all of their knowledge of the history of schooners as well as general information about the area and sea. Just absolutely calming and stunning views. Watch them hoisting the sails was really amazing, takes a lot of work. You really can't appreciate the size of them until they are right next to you. I highly recommend them and will go again! read more

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Absolutely wonderful. Staff was very attentive and always around if you needed them. Would 100% do again in a heartbeat. Only thing stopping us is leaving. read more

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We love going out on America 2.0. It is a classic yacht which sails very well. The crew is friendly and professional whether the the weather is clear or the wind is strong with rain. Enjoy the sail every time. My small grandchildren love it too. Safe for all. read more

The staff put their heart and soul into our cruise. Physically hoisting the sails and serving our food. Beautiful weather. Perfect sailing conditions. read more

Schooner America 2.0 is the Grand Dame of Key West sailing. Their sunset sails are amazing, and if you are lucky enough to sail when the wind is just right, it's absolutely exhilarating! The staff is fun and professional. There is ample space to move around and the comestibles served were delicious. I've sailed on this vessel many times, its a "WOW! read more

If you love sailing, you'll love this Key West sailing experience. Great ship, great crew.

We had a marvelous time onboard the Schooner America 2.0! My husband and I did the 1pm sail and it was so much fun! The crew was friendly and knowledgeable, water/sodas were included in our ticket. If you wanted beer or wine the price was $6. Olaf was the captain's dog and he was a such a sweet boy We absolutely recommend taking this sail read more

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A sail around Hawk Channel with Captain Janet Snell was the highlight of our Key West trip. We booked the 2pm sail. It was very relaxing. Captain Snell was happy to educate us on the workings of a ship. She is very knowledgeable. It was fascinating to watch Captain and Crew communicate and work the sails and rigging. The America 2.0 is a replica schooner, and she is by far the most beautiful ship in Key West. It is worth reading into the history of the original America. She is 105ft LOA with her main mast towering 85ft above deck. She boasts 3500sq ft of canvas sail with impeccable handling. Can you imagine rounding Cape Horn on the way to the remote California shores of the 1800's? Plenty of schooners this size made the journey. Don't miss this opportunity. read more

The crew were very enthusiastic and professional. The boat was well maintained. The sails were up but no wind on our cruise so the Captain tracked dolphin for some fun. A beautiful evening sunset. Great way to spend some time on the water. read more

The staff made the difference on this trip. Boat was great and very comfortable. Seating was planned and they left plenty of room so you weren't sitting on top of others. But as I said the staff made the most difference from the other options. They were friendly, fun and very accommodating. The free beverage selection was good and horderves were tasty. Crew served everything up so you never even had to get up. I had some confusion in my booking (my fault) and they gladly let me reschedule at the last minute. I definitely recommend Classic Harbor Line. read more

This was an amazing add on for our quick trip to the Keys. A friend has suggested we do it and it was such a fun evening! We had the most gorgeous sunset and the winds were perfect for a night of sailing. We had an all women crew which was really cool and they provided such an epic evening. Can't recommend it enough. My ONLY suggestion is that they have a hard seltzer option included with the beer, wine and cocktails :) read more

Classic Harbor Line Key West - Boat Charters Near Me - Key West, Florida