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Classic Harbor Line, Key West

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Classic Harbor Line: Key West

Dedicated to providing the 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 vessel 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 schooners 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 is 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.

Use our Key West road trip planner to arrange your visit to Classic Harbor Line and other attractions in Key West.
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Tours to Classic Harbor Line

FROM $112 BOOK WITH VIATOR Key West Sunset Sail Aboard Schooner Key West Sunset Sail Aboard Schooner

4.9

Duration: 2 hours

Tours from $112 ›

FROM $73 BOOK WITH VIATOR Key West Day Sail Aboard Schooner Key West Day Sail Aboard Schooner

4.9

Duration: 1 hour 30 minutes

Tours from $73 ›

FROM $1,032 BOOK WITH VIATOR Key West Private Morning Sail on Schooner America 2.0 Key West Private Morning Sail on Schooner America 2.0

5.0

Duration: 1 hour 30 minutes

Tours from $1,032 ›

Classic Harbor Line reviews

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1,600 reviews

By Jfloyd88

Did a sunset cruise on the America 2.0. Awesome crew, nice drinks and snacks, awesome views! A must do when visiting Key West. Nothing like a sunset from the water!

Did a sunset cruise on the America 2.0. Awesome crew, nice drinks and snacks, awesome views! A must do when visiting Key West. Nothing like a sunset from the water! more »
By betha_travel

We did the New Years Eve Bash on Schooner America 2.0 and had an absolute BLAST! Expensive, but totally worth it to see the pirate wench up close and personal and stay out of the fray. The staff...

We did the New Years Eve Bash on Schooner America 2.0 and had an absolute BLAST! Expensive, but totally worth it to see the pirate wench up close and personal and stay out of the fray. The staff... more »
By Prerna D

We choose this special Full Moon Sail for three families, 11 of us. We loved being aboard Schooner America 2.0 which is a gorgeous, large classic sail boat, working on wind power. However the staff...

We choose this special Full Moon Sail for three families, 11 of us. We loved being aboard Schooner America 2.0 which is a gorgeous, large classic sail boat, working on wind power. However the staff... more »