Captain Dan, along with crew members, Jade and Milo, made the sunset cruise absolutely marvelous! Mother Nature brought the show but the team was knowledgeable, chatty, funny, and hospitable! Special Thanks to Marie and Tom for their time chatting about the beautiful vessel and their adventure from NY to the Keys. Look forward to sailing again with you soon!
About Activity
What's Included
Includes
- 1.5-hour coastal sailing tour
- Soda and water
- 2 alcoholic drinks are included with your ticket for those 21 and older
Excludes
- Gratuities
- Hotel pickup and drop-off
- Garage parking
- Additional beer, wine, mimosas, and cocktails available for purchase onboard by credit card
Departure & Return
Departure Point
- Check-in is at the Classic Harbor Line Ticket Booth located dockside in front of the Schooner Wharf Bar at 202 William Street in Key West. The meeting point is located at the end of William St. near the corner of William St and Greene St. Parking can be found in the municipal lot on Caroline St.
Return
- Check-in is at the Classic Harbor Line Ticket Booth located dockside in front of the Schooner Wharf Bar at 202 William Street in Key West. The meeting point is located at the end of William St. near the corner of William St and Greene St. Parking can be found in the municipal lot on Caroline St.
Itinerary
Enjoy great views of Mallory Square while sailing along the coast aboard America 2.0.
See Fort Zachary from the water!
The captain will hug the coast offering great views of Sunset Pier and other famous landmarks from the water.
Language Offered
Additional Info
Cancellation Policy
Reviews
As we are seniors it was Very exciting and sometimes intense sail . The crew were excellent and knowledgeable and entertaining.
It was such a wonderful experience. The crew was amazing, and attentive. We would absolutely do this experience again, it was truly incredible!
Loved my sailing afternoon. Not as much wind as I would have liked but the crew was wonderful.
This was an exceptional experience. Highly recommended. The crew were brilliant throughout the trip. We did the 2 hour sunset trip with drinks and nibbles. This is a must if you visit Key West.
This was such an excellent experience! We enjoyed the boat, the captain, the crew, the food and the sail out further than the harbor.
Great adventure. Very friendly and informative. Have mobility issues but they were very accommodating. HIGHLY RECOMMEND.
Fantastic sunset 2 hour sail. Great crew of 3 young ladies who also served drinks & snacks. Really rocked the wind since it is a 3 masted vessel. Well worth the price.
Sailing on the America 2.0 schooner was easily one of the highlights of our time in Key West. From the moment we stepped on board, the atmosphere was calm, welcoming, and just felt different from the typical crowded boat tours. The ride itself was smooth and incredibly relaxing. There’s something about being powered by the wind that makes the whole experience feel more authentic and peaceful. The views—especially at sunset—were absolutely stunning, with that perfect golden glow over the water. The crew was friendly and attentive without being over the top, and the space on the boat made it easy to spread out and really enjoy the moment. It’s not a loud or party-style cruise, which honestly made it even better. If you’re looking for something memorable, romantic, and uniquely “Key West,” this is 100% worth it. I would absolutely do it again.
Crew was the best! Boat was beautiful! My husband and I enjoyed every moment. He helped with the sails & I got to steer a little. So cool!
What a beautiful afternoon sail on this double masted schooner! Wind and weather was perfect. Captain Janet and crew Chelsea and Dan were so skilled in maneuvering this ship in and out of the harbor, and on full sail in open water. All were so personable and a delight to sail with.
We took the excursion on the American 2.0 Schooner recommended by American Cruise Lines for an afternoon cruise around Key West. What a wonderful experience with calm seas, sunshine and a very accommodating crew. Our captain Janet along with her crew , Dan and Mary did an amazing job of making our cruise delightful.
This was a great experience. The only excursion we took and was better than we envisioned. Too short, but so fun! Don't sit in the front unless you are fine with getting drenched. Definitely would recommend it!
The schooner sail was a highlight of my trip to key west. They really do sail. Sailing is a wonderful experience- the quiet, wind and sea is a magical combination. The crew is friendly and professional. Plus they give some fun history of key west. I’d definitely go again.
First time to sail - the schooner was well kept and clean - the ride was smooth and safe- the crew was professional and attentive- would definitely recommend to others. Sail away!!!
Unique experience. Beautiful water. Excellent crew. Great way to experience the water around Key West. Definitely recommend as a must do when in the area!
Enjoyed a perfect sail with a wonderful crew. Captain Janet provided a very friendly professional sail and Jade and Milo were great. It was the perfect way to see Key West. What a wonderful afternoon on the water. Would highly recommend to anyone.
All great. Nice people. Very polite. Very professional. Obviously very experienced felt totally safe. Beautiful ship. Loved going fast by wind power. Never did before. Liked the talk about the history and the area. No complaints about anything. Everything was great.
We have sailed with American 2.0 since its first season in Key West. We are here for two months every year and try to sail once a week. The boat is amazing and if there is a little wind you will experience a thrilling ride. Brad has added a lot to the cruises if he is on the crew. His narrative on Key West history is fun and interesting. On a recent sail, Dan was captain and he added narrative on the history of the boat - very nice touch. The sunset sails allow you to see the famous sunsets of the Keys in an unforgettable way, but the day sail is relaxing on the beautiful Key West waters. You will not regret the time spent on this gem.
Amazing trip! Chelsea, Brad, and Dan were so nice and knowledgeable. The ship is beautiful and well made. I throughly enjoyed the trip!
This was our first time on a sailboat. It was a very windy day and we were a little unsure how it would go. It was a fabulous experience. Our captain and crew were the best and we had a fantastic ride. Would definitely recommend.
It was really fun, relaxing and the crew was the best. My wife is handicapped and they were helpful with questions.
I have been sailing for over 30 years around the Chesapeake Bay and this was an extremely pleasurable trip with Capt. Janet on the America 2.0. The crew was excellent but the Capt docked the 105 ft schooner into a dock that was new to her. She handled the boat extremely well. I just was impressed with her abilities and sailing knowledge. Highly recommend.
Thank you for a wonderful afternoon. The crew was knowledgeable and extremely accommodating to our group and the other guests.
Captain and crew made it a fun experience! We had a beautiful day for sailing and enjoyed the short tour from the water.
Very relaxing 2 hour, sail was not over crowded, well organized crew, very clean sail boat, had wonderful time
Great staff, beautiful boat, awesome crew. Great views of Key West! Start out in the Gulf of America into the Atlantic Ocean. Great for families or anyone else!
The crew and setting for the cruise were so classy. All four members of the crew were incredibly attentive and professional during our sail. Our cups were never empty and they treated us like we were the only people onboard the boat. We had such an amazing time and will certainly be joining again.
We were blessed with wind and had an amazing day sail! Dolphins followed us for most of the sail which added to the fun! Captain and crew were informative and super friendly! We have sailed several times on the America 2.0 and highly recommend!!! See you next year!
Excellent crew. All female. Great conversations. Small group of 10. Day sail. Saw dolphins and a shark.
The captain and crew were amazing. The service was phenomenal! The boat was wonderful. If sailing in Key West, I highly recommend this trip!
A last minute decision ended up being the highlight of our trip. We went on the Easter brunch sail. The staff was very friendly, helpful and informative. The water was beautiful and even though it was a windy day, we felt very safe.
All women crew were awesome. Beautiful sail. Such fun. Highlight of our trip. We would definitely do this again. Thank to all.
A sail around Hawk Channel with Captain Janet Snell was the highlight of our Keys trip. We booked the 2pm sail. It was very relaxing. The America 2.0 is the most beautiful vessel in Key West. We found out she is also the fastest. She is 105ft LOA with her main mast towering 85ft above deck. She boasts 3500 sq ft of canvas! Her handling is impeccable. She is a replica ship and it is worth reading into the history of the original America schooner. Can you imagine rounding Cape Horn on the way to the remote Califorina shores of the 1800s? Plenty of schooner this size made the journey. This sail is a small glimpse into history. Don't miss this opportunity.
Amazing sail on a beautiful night with great breeze - we did 11 knots ! Super fun thanks to the great Captain and crew! We’re experienced sailors and were fearful this would be too touristy but it was amazing sailing on this first Americas Cup winner replica!
Very nice boat ride. Dan, Lexi, and Chelsie were all very friendly and very knowledgeable about the craft and the area.
Great trip. Genuine sailing. Not a lot of talk. No music. Rae and Chelsey were so efficient raising the sails, coming about. Made the difficult work look easy. Very engaging and informative. Professionals.
Beautiful boat. Great, experienced crew. Buy a drinks package. The beers were ice cold. The captain got us out of the rain and into a nice, sunny area in the bay.
Relaxing afternoon after Key West hustle-bustle! Great captain and crew. Engaging and Professional. Gorgeous boat.
Loved this sail! The crew - especially our captain — was so nice and made us feel very welcome. The view of Key West from the water, and at sunset - so amazing! This was the highlight of our holiday in Key West.
Great sail in the sound. Rae, Brad and Tom were pleasant, helpful and professional, with good stories about the history of the area.
It was a small group of people, (8), which was nice, and fun and informative. The crew of 3 was great!
We’ve been visiting Key West in February for years and hone on many different sailboat trips. Our midday trip on 2/14/25 was the best by far. Sailing with full sails on this exquisite sailing vessel with a great crew was memorable. The crew, Brad, Lexie and Ray were competent, very knowledgeable and friendly Brad gave us a very amusing and surprising history of Key West. Booze was not the focus of this event. Don’t miss this iconic sailing trip.
Very relaxing and peaceful sail. Being on a real sailboat and watching (and helping) the hoisting of the sails really added to the experience. And the history knowledge shared by Brad was great.
This is a must do in Key West. They let us help with the sails and we’re all so nice. It’s a beautiful boat and ride. Rae was an amazing captain and Lexie and Brad awesome mates. They made it a beautiful experience and taught us a lot about sailing too. This is the most beautiful sail boat I’ve ever seen. We got lucky for it to be just 4 of us out of 100 person capacity. The price is nothing for the experience you’ll get. Thank you team, we’ll be back 🙏🏼👍👍👍⭐️⭐️⭐️⭐️⭐️
Classic Harbor Line was VERY accomodating. We made reservations for 14 but changed it twice. The staff there was great. When we (all 34 of us) arrived at check-in, everyone was welcomed and the crew on board were really friendly and helpful. We are a group of boaters but the crew gave an informative orientation that held our attention. The weather cooperated with moderte winds and many of our group were impressed that this schooner goes faster than our trawlers ! Everyone had a great time. We will return again next year.
We went not he schooner 2.0 for the CIVIL WAR reenactment. It was wonderful! A variety of sandwiches and macaroni salad as well as drink cards were included with the price. The day was perfect for a sail, the reenactment was well done with the Confederates on the Jolly Roger and the food and drinks were very good! The captain and crew were attentive and personable! We could not have asked for a better time and will go again! PS. There are toilets, called heads, available.
The America 2.0 is the way to go if you’re doing any kind of sail out of Key West. You really do some serious sailing but it’s a smooth ride.. I’ve also done the wreckers race and that’s a ball.
Windy, chilly afternoon January 8, 2025 sail. Experience was exhilarating, crew was totally accommodating. We spent much of the 90 minutes under sail. Ship sails up to NYC in the summer. I would look forward to an even longer day cruise in the future.
We considered backing out of our prepaid schooner cruise because of windy and very cold weather, but that would have been a mistake. We were in able hands with Janet and crew. The winds filled the sails and we had a great ride. Beautiful ship. Glad we didn’t miss it.
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