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Classic Harbor Line

202 William St, Key West, FL 33040-6645
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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.
  • Excellent92%
  • Very good5%
  • Average1%
  • Poor1%
  • Terrible1%
Travellers talk about
“sunset sail” (165 reviews)
Closed Now
Hours
Hours Today: 7:00 AM - 12:00 AM
LOCATION
202 William St, Key West, FL 33040-6645
Ways to Experience Classic Harbor Line
from US$ 91.38
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from US$ 59.12
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JPMiles / Payback Arrow
50
JPMiles / Payback Arrow
Reviews (1,187)
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All reviews
"sunset sail"
in 165 reviews
"schooner america"
in 54 reviews
"captain and crew"
in 91 reviews
"shrimp"
in 68 reviews
"cheese and crackers"
in 43 reviews
"beautiful ship"
in 31 reviews
"sailing experience"
in 45 reviews
"afternoon cruise"
in 18 reviews
"great sail"
in 27 reviews
"perfect sunset"
in 17 reviews
"key west sunset"
in 24 reviews
"beer and wine"
in 22 reviews
"party boat"
in 12 reviews
"open water"
in 12 reviews
"highlight of our trip"
in 15 reviews
"sails"
in 162 reviews
"sailboat"
in 89 reviews
Filter

1 - 10 of 1,173 reviews

Reviewed 3 days ago

We went out for a day sail on the Schooner America 2.0. What a beautiful vessel! I loved this so much, my first ever sail. The captain and crew are amazing. You can help raise the sails, and that vessel sure gets going. Smooth gorgeous...More

Thank bobunny50
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC
Reviewed 1 week ago

The Sunset Cruise was beyond what we expected. From Check in to Arrival. Total Outstanding experience. The Crew was so accommodating and friendly. We had a awesome time.

Review collected in partnership with this attraction
Thank drudruops
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC
Reviewed 2 weeks ago

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This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC
CHL745, Public Relations Manager at Classic Harbor Line, responded to this reviewResponded 2 weeks ago

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Reviewed 2 weeks ago

Gorgeous boat in every detail, great scenery, awesome experience. Nice beer and wine selection. Would recommend!

Review collected in partnership with this attraction
Thank Alison C
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC
CHL745, Public Relations Manager at Classic Harbor Line, responded to this reviewResponded 2 weeks ago

Thank you for the great review and for sailing with us! We are so glad that you enjoyed yourself and are looking forward to having you come out again next time you're in town!

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Reviewed 2 weeks ago

Great sunset sail just off Key West. Sailing vessel America boarded and departed on time. Sails were raised and drinks which included bubbly, red and white wines, beer, soft drinks and water were served. Then, trays of veggies, cheese and shrimp were nicely presented and...More

Review collected in partnership with this attraction
Thank CindyC3696
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC
CHL745, Public Relations Manager at Classic Harbor Line, responded to this reviewResponded 2 weeks ago

Thank you for the great review and for sailing with us! We are so glad that you enjoyed yourself and are looking forward to having you come out again next time you're in town!

Report response as inappropriate
This response is the subjective opinion of the management representative and not of TripAdvisor LLC
Reviewed 2 weeks ago

Can’t rave enough about our enjoyable Key West cruise. The boat is beautiful and the captain and crew were so attentive to the passengers every need. We can’t wait to do it again next year. I highly recommend.

Thank junecia
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC
CHL745, Public Relations Manager at Classic Harbor Line, responded to this reviewResponded 2 weeks ago

Thank you for the great review and for sailing with us! We are so glad that you enjoyed yourself and are looking forward to having you come out again next time you're in town!

Report response as inappropriate
This response is the subjective opinion of the management representative and not of TripAdvisor LLC
Reviewed 2 weeks ago

More

This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC
CHL745, Public Relations Manager at Classic Harbor Line, responded to this reviewResponded 2 weeks ago

More

Report response as inappropriate
This response is the subjective opinion of the management representative and not of TripAdvisor LLC
Reviewed 2 weeks ago

A group of four took the Sunset Cruise on Schooner America 2.0. It was a beautiful boat, four masts. The captain , Ron, shared tons of knowledge with us about the history of the boat (it is a replica), where we were sailing and other...More

Review collected in partnership with this attraction
Thank rowepeak
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC
CHL745, Public Relations Manager at Classic Harbor Line, responded to this reviewResponded 2 weeks ago

Thank you for the great review and for sailing with us! We are so glad that you enjoyed yourself and are looking forward to having you come out again next time you're in town!

Report response as inappropriate
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Reviewed 3 weeks ago

Excellent service. They called us 15 min ahead of boarding to make sure we were going to be on time, and knew where to go. The time on the boat was as well managed. Fantastic experience.

Review collected in partnership with this attraction
Thank Jay W
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC
CHL745, Public Relations Manager at Classic Harbor Line, responded to this reviewResponded 2 weeks ago

Thank you for the great review and for sailing with us! We are so glad that you enjoyed yourself and are looking forward to having you come out again next time you're in town!

Report response as inappropriate
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Reviewed 3 weeks ago

This was purchased for us as a wedding gift. We had a great time! VERY friendly and informative Captains - Ron, Steve and Amber. Nice sail - not too long, not too short. We would definitely recommend this trip/sail to others. Beautiful ship!!!

Review collected in partnership with this attraction
Thank Carrie K
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC
CHL745, Public Relations Manager at Classic Harbor Line, responded to this reviewResponded 2 weeks ago

Thank you for the great review and for sailing with us! We are so glad that you enjoyed yourself and are looking forward to having you come out again next time you're in town!

Report response as inappropriate
This response is the subjective opinion of the management representative and not of TripAdvisor LLC
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Ask a question
Questions & Answers
Rachel S
26 March 2017|
AnswerShow all 3 answers
Response from rwalk89 | Reviewed this property |
Both
1
Vote
cayogordo
25 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
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