Prices checked on Sep 11, 2026Things to do in Key West
Sail aboard the fastest and most elegant schooner in Key West, Schooner America 2.0! This boat is a replica of the 1851 Schooner America that won the first America's Cup Race in 1851. Admire her beauty on the clear, calm Caribbean waters while sipping a beverage. Take in views of Key West sights like Fort Zachary Taylor, Mallory Square, Sunset Pier and Sand Key Light Tower. Soda and water are complimentary. Two alcoholic beverages are included with your ticket. Additional beverages are available for purchase.
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.
Key West Day Sail on Schooner America 2.0 with 2 Drinks lasts about 1h 30min. The itinerary has 3 stops.
Prices start at $79 per person for this Key West experience, booked through Viator with the price shown before checkout. There is 1 booking option, so the final price depends on the option you choose.
Yes. Cancel at least 1 day before the start for a full refund. Later cancellations are non-refundable.
The meeting point is 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.. Hotel pickup is not part of this experience.
The experience is available in EN.
It is a small-group experience with a maximum of 68 participants.
Infants and small children can ride in a pram or stroller Kids sail FREE on our afternoon departures! All people planning to attend need to have a ticket. Please select tickets accordingly at check out for each traveler planning to attend
Yes, bookings are confirmed instantly.
It was such a wonderful experience. The crew was amazing, and attentive. We would absolutely do this experience again, it was truly incredible!
Nora, thank you for booking a sail with us and taking some time to provide your valuable feedback. We are delighted to hear about your wonderful experience and that our crew was attentive throughout your time aboard. We hope to have the opportunity to welcome you aboard again soon! - Classic Harbor Line Key West
Loved my sailing afternoon. Not as much wind as I would have liked but the crew was wonderful.
Thank you for booking a sail with us and for the great review. We hope to have the opportunity to welcome you aboard again soon! - Classic Harbor Line Key West
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.
Thank you for booking a sail with us and taking some time to provide your valuable feedback and recommendation. We are delighted to hear you had an exceptional experience on our sunset cruise. Our crew takes great pride in providing great service throughout each trip. We're thrilled the drinks and nibbles enhanced your two-hour sunset experience. We hope to have the opportunity to welcome you aboard again soon! - Classic Harbor Line 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.
Thank you for booking a sail with us and taking some time to provide your valuable feedback and recommendation. We are delighted to hear you enjoyed the trip. We hope to see you again soon! - Classic Harbor Line Key West
Great adventure. Very friendly and informative. Have mobility issues but they were very accommodating. HIGHLY RECOMMEND.
Thank you so much for sailing with us and for the great review! We hope to see you again soon! - Classic Harbor Line Key West
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.
Thank you for booking a sail with us and taking some time to provide your valuable feedback. We are delighted to hear you enjoyed the sunset aboard America 2.0 with our friendly and professional crew. It's wonderful that you appreciated the drinks, snacks, and how well our schooner handled the wind during your two-hour sail. We hope to have the pleasure of hosting you again soon! - Classic Harbor Line Key West
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.
Jamie, thank you for booking a sail with us and taking some time to provide your valuable feedback and recommendation. We are delighted to hear that sailing on the America 2.0 was a highlight of your Key West visit. Your comments about the calm atmosphere, smooth sailing, stunning sunset views, and attentive crew truly mean so much to us. We're thrilled that this experience stood out from typical tours, and we hope to have the opportunity to welcome you aboard again soon! - Classic Harbor Line Key West
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.
Jeff, thank you for booking a sail with us and taking some time to provide your valuable feedback. We are delighted to hear you enjoyed the beautiful afternoon sail on America 2.0! It's wonderful that Captain Janet and crew Chelsea and Dan made your experience so memorable with their skilled seamanship and personable service. We hope to have the pleasure of hosting you again soon! - Classic Harbor Line Key West
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.
Charles, thank you for booking a sail with us and taking some time to provide your valuable feedback and recommendation. We are delighted to hear you had a wonderful experience on the America 2.0 with smooth seas and sunshine. Captain Janet, Dan, and Mary will be thrilled to know their accommodating service made your afternoon sail around Key West so delightful. We hope to have the pleasure of hosting you again soon! - Classic Harbor Line Key West
| Tour | Duration | Rating | Price | |
|---|---|---|---|---|
| Key West Day Sail on Schooner America 2.0 with 2 Drinks | 1h 30min | 4.9 (212) | $79 | |
 Key West Small-Group Sunset Sail with Wine and Hors d'oeuvres | 2 hours | 4.9 (1,477) | $135 | View |
 All-Inclusive Sandbar Safari with Dolphin Playground Encounter | 5 hours | 4.8 (679) | $150 | View |
 Key West Sandbar Safari on One of a Kind Tiki Boat | 3h 30min | 4.7 (185) | $115 | View |
 Key West Sunset Sail with Open Bar, Live Music and Hors D'oeuvres | 2 hours | 4.7 (3,839) | $63 | View |
 Key West Half-Day Fishing Charter | 5 hours | 4.7 (497) | $95 | View |
 Key West Signature Sunset Sail with Live Music, Open Bar & Food | 2 hours | 4.5 (405) | $70 | View |