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Key West
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Classic Harbor Line
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Classic Harbor Line

See all things to do
See all things to do
Classic Harbor Line
5
1,653 reviews
#38 of 342 Boat Tours & Water Sports in Key West
Boat Tours
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7:00 AM - 12:00 AM
Monday
7:00 AM - 12:00 AM
Tuesday
7:00 AM - 12:00 AM
Wednesday
7:00 AM - 12:00 AM
Thursday
7:00 AM - 12:00 AM
Friday
7:00 AM - 12:00 AM
Saturday
7:00 AM - 12:00 AM
Sunday
7:00 AM - 12:00 AM
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About
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.
Key West, Florida
Awards
Travelers' Choice
2023
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Tours and Tickets by Classic Harbor Line
Travelers talk about
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(179 reviews)
Detailed Reviews: Reviews order informed by descriptiveness of user-identified themes such as cleanliness, atmosphere, general tips and location information.
Popular mentions
5.0
1,653 reviews
Excellent
1,543
Very good
83
Average
12
Poor
5
Terrible
10
Mammpm
South Berwick, ME26 contributions
Book it now! The best experience at the best price!
Apr 2023 • Couples
What a fantastic experience! From our initial booking with Janice at the ticket booth, to the 1.5 hour afternoon sail with only eight passengers, the trip on the Schooner America was exceptional! Ron, Tom, and Jade were engaging, knowledgeable and fun. We felt informed and welcomed from our first interaction with Janice, who was able to provide us with a military discount (IDs required).The sights were absolutely beautiful, and Ron’s narrative added information and perspective. Passengers were recruited to help hoist the sails and even take the helm for a memorable experience! It was the highlight of our week in Key West. Book in advance, and purchase some swag, because this is the most reasonably-priced and personalized sailing experience you will find in Key West!
Written April 18, 2023
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
CHL745
Hello, Thank you for sailing with us and leaving this exceptional review. We really appreciate the time that you took to share your experience and shout out the crew, and we are happy to be part of a happy memory you will have from your trip to Key West. We hope to see you again if you make your way back to the island! Warmly, Classic Harbor Line Key West
Written April 18, 2023
This response is the subjective opinion of the management representative and not of Tripadvisor LLC.
Bob F
St. Petersburg, FL11 contributions
Another great sail on America 2!
Jan 2020 • Couples
My wife & I try to sail on America 2, every time we visit Key West. This time, we brought some friends & family with us. Everyone loved it! Capt. Amber & crew are fun, friendly and extremely professional when it comes to sailing this gorgeous boat. They make quick work of hoisting the sails, setting their course and getting down to the business of serving drinks & snacks, including some mighty fine mimosas. :-) America 2 is the envy of the Key West fleet, with good reason. Being aboard when this 105-footer is under full sail, cutting though the water, is a real adventure. The boat is big, so it is roomy, comfortable and extremely stable. Non-sailors will enjoy the ride. Serious sailors are always impressed with her speed and the way the boat handles. We plan on another trip this spring and some more time on the water, onboard America 2.
Written January 20, 2020
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
Rebecca V
4 contributions
Sophisticated sunset cruise. Exhilarating, comfortable & relaxed. Beautifully looked after by highly professional crew!
Mar 2023 • Couples
The sunset cruise totally exceeded our expectations and from booking to boarding to the finish, we were looked after superbly. Both the champagne and wine we were served throughout was of an excellent quality and the nibbles, both fresh and tasty, and expertly served by the crew.
Above all the talented crew of Janet, Lexi and Rae delivered an absolutely stupendous sunset cruise, exhilarating yet comfortable, which is indelibly etched on our memories.
Thank you
Rebecca and Karel
Written March 28, 2023
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
CHL745
Hello, Thank you for sharing this eloquent review! We're so happy that we were able to exceed your expectations in terms of service, quality, and excitement. We hope to see you again any time you are in Key West! Warmly, Classic Harbor Line Key West
Written March 29, 2023
This response is the subjective opinion of the management representative and not of Tripadvisor LLC.
Getaway56409615893
3 contributions
Wreckers Race and Lighted Boat Parade
Jan 2023
We were on the America 2.0 for both the Lighted Boat Parade and the Wreckers Race. Both trips were a great experience.

The crew working the boat was excellent. They operated the vessel expertly. They were very courteous to the guests as they had to work around them to sail...as well as serve us food and drinks.

The America 2.0 is a beautiful boat, many sails and in a good wind can go pretty fast (we were going 12-13 knots). For the Wreckers Race, we had a 20MPH wind with 6-10' seas. The boat is large enough that it handled the seas without a problem, but might be an issue for those who get sea-sick easily. (this probably isn't an issue during calm seas, or during their sunset cruises).

Food and beverages served were very good.

I'd definitely recommend to others.
Written February 2, 2023
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
CHL745
Hello, Thank you for joining us for some of our special events and for taking the time to share a detailed review of your experiences. We are glad that you were able to enjoy some exciting sailing weather and that you received good service in challenging conditions. We look forward to the opportunity to host you again! Warmly, Classic Harbor Line Key West
Written February 2, 2023
This response is the subjective opinion of the management representative and not of Tripadvisor LLC.
gillespyc
Argyle, TX26 contributions
Schooner America 2.0 New Year's Eve
Dec 2022
We went aboard the Schooner America 2.0 around 9:30pm New Years Eve for the countdown to the 2023 New Year. The Schooner did stay at dock the entire time and had a countdown clock fixed to the main mast. About 10 minutes prior to the new year, a lady dressed as a Pirate Wench went up the mast and did a 10 second countdown, sliding down the mast line while swinging a sword, to 2023 New Years day.
Good food, good drinks, lots of fun. And boy what a way to ring in the new year. A first for us. Thank you to Cassy the concierge at The Marriott Key West for setting this up, and thank you to The Schooner America 2.0 crew.
Written January 20, 2023
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
CHL745
Hello, Thank you for taking the time to share your review and some details of our New Year's Eve experience. We are happy we were able to contribute to a special celebration for you, and we do hope you will consider joining us to get underway for a sail in the coming year. Warmly, Classic Harbor Line Key West
Written January 20, 2023
This response is the subjective opinion of the management representative and not of Tripadvisor LLC.
Tracey G
Effort, PA3 contributions
Great Sunset Sail!
Feb 2020
Well worth it! Beautiful ship, well run without feeling rushed. Awesome crew. About a two hour sail just in time for a fantastic Key West sunset. Motored out of dock and immediately sails went up and off we went. Exhilarating. If you have the time, do it. Basic drinks and snacks included and a cute little gift shop below deck.
Written February 15, 2020
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
PBR1234
Rochester, NY13 contributions
the best way to see the sunset from the sea
Feb 2023
We booked a same-day sunset tour on the America 2.0 and had a great time. The 4 member crew was professional and friendly and took care of the sails and the passengers interchangeably. The bubbly was very good (other options were beers, wines, soft drinks).
Written February 12, 2023
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
CHL745
Hello, Thank you for making the effort to share your review of our sunset sail. We're glad that you enjoyed your beverages and interactions with the crew, and we hope you will continue to sail with us. Warmly, Classic Harbor Line Key West
Written February 14, 2023
This response is the subjective opinion of the management representative and not of Tripadvisor LLC.
peru_doma
North Carolina60 contributions
Full Moon Sail Aboard America 2.0
Dec 2021 • Family
We choose this special Full Moon Sail for three families, 11 of us. We loved being aboard Schooner America 2.0 which is a gorgeous, large classic sail boat, working on wind power. However the staff asked our young kids to whisper in library voice who were just excited to meet & greet for first time post pandemic. We thought it to be a fun sail boat. We only booked it as one family among us was returning on it for 2nd time after having great fun before few years on same tour.. But Not Any More...Beware if you're families with small kids...don't waste your time & money..it's nothing more than a quiet booze ride which serves you tiny quick bites of cheese & crackers/cut salad and gives you a better welcome if you're buying more drinks from them aboard or want to sail quietly in library silence with them. Would not return or recommend for families though it may be great for couples or solo travelers. Key West is so much fun, everywhere, but not on this boat experience!
Written December 31, 2021
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
Tom D
Shelby Township, MI363 contributions
A wonderful night on a beautiful sailing ship
Jan 2020 • Couples
We went out for a sunset cruise and had a wonderful night. Unfortunately their wasn’t much wind and it was cloudy but it didn’t stop us from a great evening. The crew were marvelous. Beer, wine and soft drinks were served. They brought around a veggie tray, cheese and crackers and then shrimp. Cruise lasted two hours.
Written January 25, 2020
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
Wanderer
6 contributions
Great Sailing Experience
May 2021
This was a great experience in Key West. The crew was very friendly and attentive, basically as many drinks as you wanted (beer, wine, soft drinks, think you may pay extra for champagne but not sure). The snacks were simple but hit the mark. Very friendly atmosphere, everyone talkative sitting around us. Two hours was just right on the water. Don't worry about standing in line early to get a good spot, they have assigned seats when you board so waiting in line serves no purpose--just don't be late for departure! Well run operation, would do it again!
Written May 12, 2021
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
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