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,
End of the season highlight reel for JADE!!
While Jade is 100% NOT “drunk and outside” when she’s working, the energy of this song captures her spirit perfectly. (Did you see her open that can with her toes?!? Also, definitely not while working).She brings a fun energy to the boat every single day and is always willing to help out with social media 🙃. Jade is a hard worker and a great teacher. Jade has her captains license and will be driving boats in Key West this summer when America2.0 heads north.
Thanks for a great season Jade!!
05/22/2026
MONDAY MONDAY MONDAY!
The sunset sail on Monday 5/25 is our last sail before we bring the boat up to NYC for the summer season. The wind is up and the sunsets have been STUNNING! Come join us one more time before we head north!
Ready for a life change?? We’re living those sailor girl/LOSTBoy dreams every day down here in Key West!
Here are some clips from our photo shoot with Key West’s very own LostBoyCreations.
05/17/2026
"This was the best sunset cruise my husband and I have gone in Key West. It is affordable enough to do it every time you are in the keys. Extremely friendly and professional crew. The sailing experience was breath taking and romantic. We even ran into dolphins. We can not wait to return. Must do in Key West." says Sonia on Google
Classic Harbor Line Key West | Key West, FL ★★★★★ This was the best sunset cruise my husband and I have gone in Key West. It is affordable enough to do it every time you are in the keys. Extremely friendly and professional crew. The sailing experience was breath taking and romantic. We even ran into dolphins. We can not wait to retu...
05/17/2026
"Beautiful sail!! Great crew! Janet, Jade, Tygo" says DAWN on Google
Classic Harbor Line Key West | Key West, FL ★★★★★ Beautiful sail!! Great crew! Janet, Jade, Tygo
Ahhhhhh golden hour sailing 💛⭐️🔱
05/16/2026
"Beautiful sail in to the Gulf led by experienced and thoughtful crew." says Joel on Google
Classic Harbor Line Key West | Key West, FL ★★★★★ Beautiful sail in to the Gulf led by experienced and thoughtful crew.
When “I want to go to sailing camp!” Turns into taking passengers sailing on a 105’ boat to see the sunset off the coast of Key West. Isn’t it amazing how life turns out??
05/10/2026
"Lovely sail along the Key West Coast! We had a wonderful time and had great service (super friendly crew) from Milo, Chelsea, Dan, Brad (or Brian...sorry). Anyway they were great! We will definitely go again!" says Lisa
Lisa S.'s review of Classic Harbor Line Key West Lovely sail along the Key West Coast! We had a wonderful time and had great service (super friendly…
05/10/2026
"I had a Sailboat ride, It was amazing and the crew are just welcoming and served the best." says Siddartha on Google
Classic Harbor Line Key West | Key West, FL ★★★★★ I had a Sailboat ride, It was amazing and the crew are just welcoming and served the best.
Click here to claim your Sponsored Listing.
Category
Telephone
Website
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 |