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 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.

On this day in 1851, the U.S. schooner America won the first race for the 100 Guineas Cup around the Isle of Wight, an e...
08/22/2025

On this day in 1851, the U.S. schooner America won the first race for the 100 Guineas Cup around the Isle of Wight, an event that led to the creation of the America's Cup trophy, the world's oldest continually contested sporting prize.

And we are so glad she did!!

ON THIS DATE in 1851 the schooner yacht America raced against 15 yachts of the Royal Yacht Squadron in the Club's annual 53-nautical-mile regatta around the Isle of Wight. America won, finishing eight minutes ahead of the closest rival. Apocryphally, Queen Victoria, who was watching at the finish line, was reported to have asked who was second, the famous answer being: "Your Majesty, there is no second."

Commodore John Cox Stevens, a charter member of the fledgling New York Yacht Club, had formed a six-person syndicate to build a yacht with intention of taking her to England and competing in yachting regattas and match races. The syndicate contracted with designer George Steers for a 101' schooner, which had been christened America and launched on 3 May 1851.

Boat hair don’t care! 💁🏽‍♀️Hairrrrr me out (ha… ha… do you seaaaaaa what I did there?):          -a HAIR-o-meter for win...
08/11/2025

Boat hair don’t care! 💁🏽‍♀️

Hairrrrr me out (ha… ha… do you seaaaaaa what I did there?):
-a HAIR-o-meter for wind…

08/05/2025
"Would highly recommend, we did this for July 4th and it was super fun! Great weather and the crew was very welcoming!" ...
07/04/2025

"Would highly recommend, we did this for July 4th and it was super fun! Great weather and the crew was very welcoming!" says Alice on Google

★★★★★ Would highly recommend, we did this for July 4th and it was super fun! Great weather and the crew was very welcoming!

"Paseo muy bonito, todo el staff es muy amable y servicial. Totalmente recomendado" says Claudia on Google
07/03/2025

"Paseo muy bonito, todo el staff es muy amable y servicial. Totalmente recomendado" says Claudia on Google

★★★★★ Paseo muy bonito, todo el staff es muy amable y servicial. Totalmente recomendado

06/03/2025

"Thank you so much for a wonderful experience!! The ship is beautiful and clean. The staff were knowledgeable , friendly and very good at their job. Plus it was very safe. It was the best way to see the Florida Keys sunset. Which is one of the best in the world. The appetizers were surprisingly delicious too." says Maria

"Did a sunset cruise as one of our wedding activities. Couldn’t recommend it enough! It was the best time with family an...
05/29/2025

"Did a sunset cruise as one of our wedding activities. Couldn’t recommend it enough! It was the best time with family and friends and we all got to see an unforgettable sunset." says Casey on Google

★★★★★ Did a sunset cruise as one of our wedding activities. Couldn’t recommend it enough! It was the best time with family and friends and we all got to see an unforgettable sunset.

"Unforgettable.  Amazing sailing with this crew   Great food and beverages. Amazing sunset evening" says M on Google
05/23/2025

"Unforgettable. Amazing sailing with this crew Great food and beverages. Amazing sunset evening" says M on Google

★★★★★ Unforgettable. Amazing sailing with this crew Great food and beverages. Amazing sunset evening

05/22/2025

"If you love sailing, you'll love this Key West sailing experience. Great ship, great crew." says Charlie

"A beautiful ship piloted by an extraordinary captain and crew. We were served veggie plates, cheese and crackers, drink...
05/21/2025

"A beautiful ship piloted by an extraordinary captain and crew. We were served veggie plates, cheese and crackers, drinks, shrimp cocktail and brownies. The trip was smooth with interesting local history presentation along the way. Highly recommeded!" says Michael on Google

★★★★★ A beautiful ship piloted by an extraordinary captain and crew. We were served veggie plates, cheese and crackers, drinks, shrimp cocktail and brownies. The trip was smooth with interesting local history presentation along the way. Highly recommeded!

"Had a wonderful time on sunset cruise in Key West.   Rae, Dan and Brad were great. So nice and friendly.  Very attentiv...
05/18/2025

"Had a wonderful time on sunset cruise in Key West. Rae, Dan and Brad were great. So nice and friendly. Very attentive to our needs. The food and drinks were good. Highly recommend!" says jo on Google

★★★★★ Had a wonderful time on sunset cruise in Key West. Rae, Dan and Brad were great. So nice and friendly. Very attentive to our needs. The food and drinks were good. Highly recommend!

"We did the moonlight sail, and it was fantastic! The crew was excellent, and I would love to try some of their other tr...
05/18/2025

"We did the moonlight sail, and it was fantastic! The crew was excellent, and I would love to try some of their other trips. Highly recommended." says Caren on Google

★★★★★ We did the moonlight sail, and it was fantastic! The crew was excellent, and I would love to try some of their other trips. Highly recommended.

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

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