Sunset Just Got Upgraded
Our Most Popular Cruise!
Key West Champagne Sunset Sail
Enjoy your romantic sunset sail aboard Key West’s most elegant sailboat, the 105-foot, 1851 revival, Schooner America 2.0.
Classic Harbor Line Key West —
Simply the Best Sailing in Key West!
Classic Harbor Line is proud to offer Key West sailing tours aboard Schooner America 2.0, a 105-foot replica of the 19th-century Schooner America (the first America’s Cup winner!). Sunset sails, sightseeing cruises, and even nighttime cruises provide scenic views of Key West’s coastline, and some of the best sailing in Key West.
Our guests can enjoy the thrill of sailing, complemented by friendly crew members eager to share their knowledge. Equipped with comfortable amenities, Schooner America 2.0 blends nautical heritage with modern comfort, making it a standout choice for visitors
seeking the perfect way to explore the waters of Key West.
As designer, builder, and operator of classically-inspired boats up and down the East Coast, we know the recipe for the perfect cruise in Key West. Built in 2011, Schooner America 2.0 features teak decks, comfortable bench seating, and 3600 square feet of canvas!
Sit back and relax while our five-star crew sails her effortlessly through the waters and off towards the horizon for the quintessential Key West sailing experience!
“Wonderful sunset cruise! We highly recommended jumping aboard this massive ship and joining the amazing crew for a lovely evening out on the water. Janet is a highly skilled captain ready to answer all your questions and her crew do an amazing job to cater to all your needs. They allow you to help put up the enormous sails and steer the ship if it suits your fancy. Our favorite sunset cruise in KW yet. 10/10 would do again!!”
– Sunset Cruise Customer
About
Dedicated to exceeding expectations for locals and visitors alike while they enjoy the unique wonders of Key West from the water, Classic Harbor Line hopes for the privilege of hosting you on a relaxing, inspiring, and breathtaking Key West boat tour. Schooner America 2.0 is reminiscent of the classic boats that sailed the Key West waterways over the last two centuries. Read more >
News
And Events
Read more about our Key West sightseeing cruise offerings, special events, and the history of Classic Harbor Line.
Best Key West Sunset Sail
Shout out from Key West Food Tours
Florida Weekly: Key West Edition
Get tickets now!
Come sail with us for the SAIL PHILADELPHIA event!
Sailing aboard Schooner America 2.0 in Key West
