Sunset Sailing: Key West Schooner America 2.0 Tour

850 Ratings

Key West

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Embark on an elegant sunset sailing adventure aboard the stunning Schooner America 2.0 in Key West. Enjoy complimentary beverages, hors d’oeuvres, and breathtaking views of the Florida sunset.

Duration: 2 hours

Cancellation: 24 hours

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Highlights

Mallory Square - Enjoy views of some famous Key West landmarks from the water as the boat sails along the coast and onward into the sunset!
Fort Zachary Taylor Historic State Park - See the famous Fort Zachary from the water as you sail by.
Sunset Pier - Enjoy great waterside views of Sunset Pier and other famous Key West landmarks as the captain sails America 2.0 alongside the coastline and onward!

What's Included

Complimentary beer, wine, Champagne, and soda
2-hour sailing aboard America 2.0
Individually plated hors d’oeuvres

What's Not Included

Gratuities
Hotel pickup and drop-off

Additional Information

Embark on a delightful 2-hour evening sailing excursion on a beautiful contemporary schooner! Soak in the views on board Schooner America 2.0, the most distinguished schooner in Key West, as you pass by landmarks like Mallory Square, Sunset Pier, and Sand Key Light Tower. Benefit from free beverages throughout your sail along with individually served…

Location

202 William St

William Street

Check in is located dockside in front of the Schooner Wharf Bar at 202 William Street in Key West, 33040. Our ticket booth is located at the end of William Street near the corner of William St and Greene St. Parking can be found in the municipal lot on Caroline St.

Cancellation Policy

For a full refund, cancel at least 24 hours before the scheduled departure time.

Customer Ratings

4.9

(850 Ratings)

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Kdelaneyprice

Mar 24, 2026

Beautiful sailing experience - This sunset sail was the perfect way to watch the sunset. The crew took excellent care of us. Our drinks were never empty and the apps were perfectly light and filling. We sailed the whole trip except for in and out of the marina which was awesome. Saw dolphins who were jumping in our wake which was a highlight. The sunsets in key west are killer and this is a great relaxing and sweet way to watch it. It was between this sunset sail and a party boat for my husband and I on an anniversary trip and this was definitely the right move.

Review provided by Tripadvisor

I600iwricharda

Mar 23, 2026

A spectacular evening sailing adventure with the best of friends. - My wife and I and three other couples enjoyed and spectacularly beautiful evening on a Key West Schooner Sunset Sail (by Classic Harbor Line). The very capable young adult crew did an outstanding job of handling the ship and cheerfully provided 4 different simple but delicious Hors d'oeuvres plus a selection of liquid refreshments including adult beverages. The crew members were friendly, informative and sociable. The ship was well maintained and in excellent condition. The view of the sunset was amazing. In all respects this was a very memorable experience. I highly recommend this experience for your next trip to Key West.

Review provided by Tripadvisor

Robin_m

Mar 21, 2026

Great sail - This was a fantastic sail. Staff was great. Capt Janet was great too. Food was nice too. We had ranch and veggies, cheese and crackers, boiled shrimp and a brownie for dessert. The drinks were free flowing also. I would do this again on the next visit. The only problem is finding the ticket booth. We went to three different ones before we found the correct one. It could be market for easier access.

Review provided by Viator

Davidjohn_g

Mar 21, 2026

Great trip on the schooner! - Our outing was wonderful - smaller group of people, attentive and knowledgeable crew - Rae, Chelsea, and Brad - great night overall.

Review provided by Viator

Cogirl68

Mar 20, 2026

Great trip! - Awesome time on the America 2.0, and the crew - Rae, Chelsea, and Brad - was fantastic. Great experience to see the hoisting of the sails once we were out on the open water. The food was good, nothing flashy, but tasty. The sunset was beautiful and we even had a bonus dolphin sighting along the way. We enjoyed this trip from start to finish!

Review provided by Tripadvisor

Kelley_f

Mar 20, 2026

Great Day to Sail! - It was a great sailing day. Good wind. Crew was excellent and very professional. The drinks and hors dourves were good. The crew was very organized in their service of the snacks. The captain and crew were enthusiastic and informative.

Review provided by Viator

Randy_c

Mar 20, 2026

Prepare to be amazed!... - Prepare to be amazed! Especially if it’s your first time on a sail boat. Captain Janet and crew were phenomenal in every sense!

Review provided by Viator

521987

Mar 19, 2026

No sunset but what a great night for sailing - Our 2nd time out with America 2.0! Once again a memorable evening with Janet, Jade and Heather this time. Crew is friendly and works successfully to make sure all are well taken care of. We had no sunset to see on this chilly, cloudy evening but Janet provided an awesome sail (it was windy!), conversation and pointing the sites around Key West. We saw quite a few dolphins too which we were able to capture on video -a wonderful surprise! No doubt about it we’ll be back again on our next Key West vacation!

Review provided by Tripadvisor

William_m