We noticed that you're using an unsupported browser. The TripAdvisor website may not display properly.We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

Classic Harbor Line

202 William St, Key West, FL 33040-6645
+1 305-293-7245
Call
Website
Save
Book In Advance
More Info
US$59.12*
and up
Classic Day Sail Aboard America 2.0
More Info
US$91.38*
and up
Key West Sunset Sail Aboard Schooner America 2.0
Map
Satellite
Map updates are paused. Zoom in to see updated info.
Reset zoom
Updating Map...
Overview
More
Classic Harbor Line, operating renowned day sail operations in Newport, RI, New York City, Boston,MA, Hoboken,NJ,and bring the glorious America 2.0 to Key West, Florida. The 105-foot, 1800s vessel is captained by US Coast Guard certified captains and only the most professional and courteous crew you will ever meet. America 2.0 is truly the diamond shining amongst the Key West Schooner Fleet. She is a close cousin to Key West's former pride, Schooner America. Guests are sure to have a comfortable ride on this fast and lively schooner. Dedicated to providing the most 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 vessels 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.
  • Excellent91%
  • Very good6%
  • Average1%
  • Poor1%
  • Terrible1%
Travellers talk about
“sunset sail” (152 reviews)
Closed Now
All hours
Hours Today: 07:00 - 00:00
LOCATION
202 William St, Key West, FL 33040-6645
CONTACT
Website
+1 305-293-7245
Write a ReviewReviews (1,046)
Traveller rating
Traveller type
Time of year
Language

1 - 10 of 1,033 reviews

Reviewed 2 days ago

Perfect evening with a friendly captain and mates. Guests were low key, which was really nice.... no loud screamers here. Just a relaxing sail with wine and cheese. Nice trip!

Review collected in partnership with this attraction
Thank ninafbailey
Reviewed 2 days ago

More

Thank Dan T
Reviewed 3 days ago

My family and I recently sailed on the Schooner America 2.0's afternoon mimosa cruise. We could not have asked for a better afternoon. The crew was personable, professional, and was genuinely interested in ensuring our comfort throughout the sail. I would highly recommend Classic Harbor...More

Review collected in partnership with this attraction
Thank bandit1212
Reviewed 6 days ago

The America 2.0 is a beautiful boat, the crew is awesome, and the sunset was breathtaking. Definitely worth the price! This sail is a must during your trip in Key West!

Review collected in partnership with this attraction
Thank jaytraveler429
Reviewed 1 week ago

Crew was friendly, engaging and expert in all matters of the sail. They were very attentive to details shared with them and freely shared their tips and experiences. Had a smooth sail on a great day of weather.

Review collected in partnership with this attraction
Thank Michael M
CHL745, Manager at Classic Harbor Line, responded to this reviewResponded 6 days ago

Hello, Thank you for sharing your experience. We are happy to hear that you had a perfect Key West Sailing Day! We hope to have you out with us again in the future. Warmly, Classic Harbor Line

Reviewed 1 week ago

Beautiful classic sailboat, great crew, hors d'oeuvres & champagen (other drinks available)...and of course, an amazing sunset on the water!

Review collected in partnership with this attraction
Thank debramD6162XS
CHL745, Manager at Classic Harbor Line, responded to this reviewResponded 6 days ago

Thank you for your recommendation! We hope to have you out with us again soon! Warmly, Classic Harbor Line

Reviewed 1 week ago

More

Thank rikkirocket
CHL745, Manager at Classic Harbor Line, responded to this reviewResponded 6 days ago

More

Reviewed 1 week ago

More

Thank Michael T
CHL745, Manager at Classic Harbor Line, responded to this reviewResponded 6 days ago

More

Reviewed 2 weeks ago via mobile

The Classic Day Sail aboard America 2.0 was absolutely a perfect way to spend a sunny Key West afternoon. The ship is beautiful and perfectly maintained and the crew knowledgeable and charming. So nice to relax and enjoy sailing!More

Thank ROTTERDAN62
CHL745, Manager at Classic Harbor Line, responded to this reviewResponded 6 days ago

Hello, We are very happy that you got to kick back and relax! Thank you for joining us on the Schooner America 2.0 and sharing your experience. We hope to have you out with us again in the future (If not here in Key West...More

Reviewed 2 weeks ago

We highly recommend, crew and boat were wonderful and we had a great time. Beautiful way to enjoy the Key West sunset.

Review collected in partnership with this attraction
Thank Enrique C
CHL745, Manager at Classic Harbor Line, responded to this reviewResponded 6 days ago

Hello Enrique, We want to thank you for sharing your experience and recommending us to friends and family. We hope to have you out with us again in the future. Warmly, Classic Harbor Line

Nearby
Nearby Restaurants
Cuban Coffee Queen
2,368 reviews
.11 miles away
Duetto Pizza and Gelato
2,296 reviews
.15 miles away
Eaton Street Seafood Market
894 reviews
.17 miles away
Kermit's Key West Key Lime Shoppe
2,236 reviews
.05 miles away
Nearby Attractions
Sebago Key West
3,208 reviews
.03 miles away
Dolphin Watch
749 reviews
.08 miles away
Schooner Jolly II Rover
808 reviews
.05 miles away
Ask a question
Questions & Answers
Rachel S
26 March 2017|
AnswerShow all 3 answers
Response from rwalk89 | Reviewed this property |
Both
1
Vote
cayogordo
24 January 2017|
Answer
Response from CHL745 | Property representative |
Hi Gordon, Apologies for the phone issues. If you ever need to make a booking and can't get through on the phone, please email us the details (minus the credit card info, of course) at info @ sail-keywest. com. We can take... More
0
Votes
Mark Z
12 January 2016|
Answer
Response from Judith H |
Sunset cruise is around 2 hours. There is veg and dips, cheese and crackers, shrimp served and wine, beer and soft drinks.
0
Votes