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
Website
Share
Save
Book In Advance
Tours from Classic Harbor Line tend to sell out - travelers recommend booking in advance!
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.
  • Excellent92%
  • Very good5%
  • Average1%
  • Poor1%
  • Terrible1%
Travelers talk about
“sunset sail” (160 reviews)
Closed Now
Hours
Hours Today: 7:00 AM - 12:00 AM
LOCATION
202 William St, Key West, FL 33040-6645
CONTACT
Website
+1 305-293-7245
Ways to Experience Classic Harbor Line
from $59.12
More Info
from $91.38
More Info
Write a ReviewReviews (1,190)
Traveler rating
Traveler type
Time of year
Language
All reviews
"sunset sail"
in 160 reviews
"schooner america"
in 54 reviews
"captain and crew"
in 90 reviews
"shrimp"
in 68 reviews
"cheese and crackers"
in 43 reviews
"beautiful boat"
in 49 reviews
"sailing experience"
in 43 reviews
"wreckers race"
in 11 reviews
"afternoon cruise"
in 18 reviews
"great sail"
in 26 reviews
"beautiful evening"
in 11 reviews
"perfect sunset"
in 16 reviews
"beer and wine"
in 22 reviews
"green flash"
in 11 reviews
"key west sunset"
in 21 reviews
"party boat"
in 12 reviews
"open water"
in 12 reviews
Filter

1 - 10 of 1,175 reviews

Reviewed 1 week ago via mobile

More

This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.
Reviewed May 26, 2018 via mobile

Enjoyed a lovely 90 minute cruise aboard the America 2.0 in Philadelphia. Captain and crew were helpful and informative. Wonderful way to spend the day!

Thank franterand
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.
Reviewed May 20, 2018

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.
See more reviews
Reviewed May 16, 2018

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 May 8, 2018

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 May 9, 2018

More

Report response as inappropriate
This response is the subjective opinion of the management representative and not of TripAdvisor LLC.
Reviewed May 7, 2018

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 May 9, 2018

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 May 7, 2018

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 May 9, 2018

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 May 6, 2018

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 May 9, 2018

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 May 3, 2018

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 May 9, 2018

More

Report response as inappropriate
This response is the subjective opinion of the management representative and not of TripAdvisor LLC.
Reviewed May 3, 2018

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 May 9, 2018

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.
Nearby
Nearby HotelsSee all 51 hotels in Key West
The Marker Waterfront Resort
1,764 reviews
.03 miles away
Cypress House Hotel : Key West
552 reviews
.13 miles away
The Galleon Resort And Marina
534 reviews
.17 miles away
Hyatt Centric Key West Resort and Spa
2,599 reviews
.21 miles away
Nearby Restaurants
Fisherman's Cafe
211 reviews
.03 miles away
Cuban Coffee Queen
2,534 reviews
.11 miles away
Duetto Pizza and Gelato
2,414 reviews
.15 miles away
Eaton Street Seafood Market
1,063 reviews
.17 miles away
Nearby Attractions
Key West Historic Seaport
586 reviews
.07 miles away
Dolphin Watch
828 reviews
.08 miles away
Schooner Spirit of Independence
445 reviews
.01 miles away
Ask a question
Questions & Answers
Rachel S
March 26, 2017|
AnswerShow all 3 answers
Response from rwalk89 | Reviewed this property |
Both
1
Vote
cayogordo
January 24, 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