Classic Harbor Line - Key West

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Classic Harbor Line - Key West Classic Harbor Line brings the 105-foot Schooner America 2.0 (of NYC,NY) to Key West for a winter of sunset sailing

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 Ch*****ne 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.

10/21/2026

A Warm salty breeze, no engine noise, a beautiful sunset and time spent with friends and family on a sunset sail is just what the doctor ordered.

10/17/2026

Need a date idea? Take me sailing.

10/12/2026

“I bet the boat is really missing me right now”- yup. She is.

Feeling a little blue after hauling out for the season? We get it. Luckily we’re on an opposite schedule down here and we sail ALLLLLL WINTER!

10/09/2026

Another Sunset sail on America2.0 it is I guess…

Just remember, the cheapest part of the boat ownership process is buying the boat. Soooooo we got you 😚😎.

10/07/2026

Don’t worry mom & dad, I’m good. 🫶🏼✌🏼

10/05/2026

Happy birthday to Captain Dan! He keeps the crew and guests smiling every day! He’s a fantastic sailor and an even better friend! We love ya Dan and are so proud to have you as part of our crew!

10/04/2026

Sailing maintenance is a labor of love! The no’s aren’t fun but they’re necessary! Do you spend more time doing maintenance or sailing?

10/01/2026

DND activated. ✌🏼⛵️🧘🏻‍♀️

09/28/2026

Sailing hard AND keeping up with trends… sometimes it means turning sailors into subjects but they’re pretty good sports about it!

09/20/2026

Forever see me on the water with a margarita or cold b**r. Unless it’s cold outside and then see me in KEY WEST, on the water, with a margarita or cold b**r.

Address

202 William Street
Key West, FL
33040

Opening Hours

Monday 9am - 7pm
Tuesday 9am - 7pm
Wednesday 9am - 7pm
Thursday 9am - 7pm
Friday 9am - 7pm
Saturday 9am - 7pm
Sunday 9am - 7pm

Telephone

(305) 293-7245

Website

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