Classic Harbor Line - Key West

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.

08/30/2026

“Smooth sailing America!”

Kinda chic to be classic AND cute!!

08/22/2026

On August 22, 1851, our name sake, the Schooner America, won the race that ultimately gave the America’s Cup its name.

She raced around the Isle of Wight, England, against 14 British yachts for the Royal Yacht Squadron’s Hundred Guinea Cup. America overcame a poor start, moved through the fleet, and finished well ahead of her closest rivals.

One of the most famous stories from the race says Queen Victoria, watching from the royal yacht, asked who was second. The reported reply was:

“Your Majesty, there is no second.”

The exact wording is part of sailing lore, but the story became inseparable from America’s victory.

references

08/20/2026

It’s always on the 5 in Margaritaville!!! The Keys are calling and it’s time to answer.

08/19/2026

Sailing in History. On August 19, 1812 Navy ship USS Constitution earned her nickname “Old Ironsides”. Today she remains in Charlestown Navy Yard in Boston, crewed by active-duty U.S. Navy sailors.

08/17/2026

The job description can be very broad. Trim sails, sand/varnish, clean the head, cut cheese, pour w**e, organize retail, stay up to date on all drills and certifications, haul sails. The list goes on. It’s always different and Most of the time a lot of fun!

08/11/2026

Common mistake that always feels like nails on a chalkboard. And yes, this gives our sailing buddies the right to call us out when it happens to us…. But to be fair I’m sure we forgot because we were probably busy giving our guests first class drink service 💁🏼‍♀️

08/09/2026

sea legs might get used to sailing at a 25degree angle all the time but our land legs are confused. We might not need gym memberships but we’d be thrilled if we could get some punch cards to the chiropractor!

08/04/2026

ITS A SAIL SALE!!!! We miss all of our Key West America2.0 family soooooo much! America2.0 returns to the Key West Bight the end of October and to celebrate the incoming start of the Key West sailing season we’re offering a 15% off discount for November sails. The Promo is live on our website so get your tickets now!! Check the link in our bio for more info and to schedule your sail.

We can’t wait to see you on board in NOVEMBER!

07/29/2026

🚩🚩also while we’re at it… it’s a line, not a rope and schooner is pronounced SKOOOOOOONER.

07/21/2026

That glorious feeling when everyone around the dock is watching you… and you NAIL a difficult docking.

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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