Dedicated to providing the most perfect hospitality and sailing experience one could find in Key West, Classic Harbor Line hopes for the privilege of escorting you on a breathtaking excursion aboard the most elegant vessels in the local Key West fleet: Schooner America 2.0. While visiting Key West, Florida you will find a number of land and water based activities. However, a classic schooner sail, whether it be a day sail, or sunset sail, is well known to be the quintessential Key West activity that will highlight your stay and be the lasting memory forever.

South Florida sightseeing is all about getting on the water, seeing the wildlife, watching the Key West sunset with a loved one, and experiencing the adventure sailing in the great Key West Florida breeze. A 2 hour sailboat ride is a great way to take advantage of your time in Key West to enjoy all of these things.

Whether buying tickets for one of our Champagne Sunset Sails, Afternoon Key West day sail, Full Moon, Star-Gazer Sails; or Privately Chartering the schooner’s for a special family event or corporate event, you will be amazed by America 2.0's beauty and comfort. It is maintained by the same creators of Key West’s former pride, Schooner America.

Classic Harbor Line in not only known for operating with amazing sailboats and classic yachts in Boston, New York, Newport, and Key West, but they are also renowned for their outstanding hospitality and customer service. You will find your captain and crew extremely capable, accommodating, helpful, and friendly whether you are spontaneously buying tickets for a classic day sail or planning your one-of-a-kind wedding day.

Local

Eat and Drink

• Classic Harbor Line - Key West (0.0 miles) - Dedicated to providing the most perfect hospitality and sailing experience one could find in Key Wes...
• Smokin Tuna Saloon - Key West (0.3 miles) - SMOKIN’ TUNA SALOON “There’s Something Fishy going On" The Best Kept Secret in Old Town Key...
• Key West Pub Crawl - Key West (0.3 miles) - Are you looking for the ultimate Key West tradition? Come along and do the “Duval Crawl™”. Key...
• Bone Island Haunted Pub Crawl - Key West (0.3 miles) - Are you ready for some "spirited" fun? Join us on a spine-tingling adventure through Bone Is...
• Bone Island Haunted Pub Crawl - Key West (0.3 miles) - Are you ready for some "spirited" fun? Join us on a spine-tingling adventure through Bone Is...

See and Do

• Classic Harbor Line Key West (0.0 miles) - Dedicated to providing the most perfect hospitality and sailing experience one could find in Key Wes...
• Sunset Sail Key West Key West (0.0 miles) - Offering exclusive private sailing charters on your choice of great classic boats. Sunset Sail Key We...
• Classic Harbor Line Key West (0.0 miles) - Dedicated to providing the most perfect hospitality and sailing experience one could find in Key Wes...
• Key Lime Bike Tours Key West (0.2 miles) - Cruising the best of Old Key West! Join us on a leisurely tour around historic Key West, the souther...
• Key West Pub Crawl Key West (0.3 miles) - Are you looking for the ultimate Key West tradition? Come along and do the “Duval Crawl™”. Key...

Shopping

• Smokin Tuna Saloon - Key West (0.3 miles) - SMOKIN’ TUNA SALOON “There’s Something Fishy going On" The Best Kept Secret in Old Town Key...