Classic Harbor Line
Classic Harbor Line
5
9:00 AM - 9:00 PM
Monday
9:00 AM - 9:00 PM
Tuesday
9:00 AM - 9:00 PM
Wednesday
9:00 AM - 9:00 PM
Thursday
9:00 AM - 9:00 PM
Friday
9:00 AM - 9:00 PM
Saturday
9:00 AM - 9:00 PM
Sunday
9:00 AM - 9:00 PM
About
Classic Harbor Line, based in Key West, offers premier boat tours and charters. Established with a commitment to providing exceptional sailing experiences, Classic Harbor Line has become a staple in Key West's maritime tourism industry. They offer a unique and luxurious way to explore the picturesque waters surrounding Key West aboard the prized Schooner America 2.0, a 105-foot sailing yacht built in 2011. With the Schooner America 2.0, Classic Harbor Line provides a range of tours, including afternoon sails, sunset cruises, private charters, and specialty excursions that showcase the beauty and charm of the Florida Keys. The experienced and knowledgeable crew adds to the overall excellence of the Classic Harbor Line experience. Their expertise not only ensures the safety of passengers, but also enhances the journey with fascinating insights into Key West's maritime history and ecology. Classic Harbor Line also operates in Newport RI, New York, NY, and Boston MA
Key West, Florida

Awards
Travelers' Choice
2023

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Tours and Tickets by Classic Harbor Line
Travelers talk about
(179 reviews)
(69 reviews)
(47 reviews)

Most Recent: Reviews ordered by most recent publish date in descending order.

Detailed Reviews: Reviews ordered by recency and descriptiveness of user-identified themes such as wait time, length of visit, general tips, and location information.

Popular mentions

5.0
5.0 of 5 bubbles1,738 reviews
Excellent
1,630
Very good
83
Average
13
Poor
5
Terrible
10

Mammpm
South Berwick, ME28 contributions
5.0 of 5 bubbles
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.
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
5.0 of 5 bubbles
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
5.0 of 5 bubbles
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.
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
5.0 of 5 bubbles
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.
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, TX28 contributions
5.0 of 5 bubbles
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.
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.

B H
6 contributions
5.0 of 5 bubbles
Feb 2024 • Couples
We sailed on America 2.0 in the Feb 2024 Wrecker race. Janet was a great Captain, winning handily, but also explaining a bit about sailing and the Wrecker's Cup as we went. The crew was fantastic, the food was outstanding and the drink selection was great. It was fun watching the crew work the sails and seeing the Captain lead them on. It was an afternoon well spent and we'd highly recommend it if you're in Key West on the Sundays they race.
Written February 27, 2024
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.
Thank you for booking a Wrecker's Race sail with us and taking some time to leave a review. It is fun to hear that you were able to have a great experience watching Captain Janet and her crew put in a winning effort while also providing friendly service. We appreciate the recommendation and hope to have the pleasure of sailing with you again if you return to Key West! - Classic Harbor Line Key West
Written February 28, 2024
This response is the subjective opinion of the management representative and not of Tripadvisor LLC.

Clay H
1 contribution
5.0 of 5 bubbles
Feb 2024 • Couples
We did the sunset sail and had a really good time. Two days later we saw the forecast was for 25 kts so we signed up again for the day sail. It was a great time! These sailors love to show off what their boat can do and I was really impressed with how they handled the boat. Other charters cancelled that day but our crew sailed the America almost all the way back to the slip. Awesome!
Written February 7, 2024
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.
Thank you for booking a sunset sail and then another day sail with us and taking some time to leave a review. It is wonderful to hear that you were impressed by the skills of the crew and the performance of America 2.0 enough to seek us out on a day with extra adventurous conditions. We are glad that the second trip was just as good, and we hope to see you again for more thrills! - Classic Harbor Line Key West
Written February 8, 2024
This response is the subjective opinion of the management representative and not of Tripadvisor LLC.

Tracey G
Effort, PA3 contributions
5.0 of 5 bubbles
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
5.0 of 5 bubbles
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.
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.

John O
3 contributions
5.0 of 5 bubbles
Feb 2024 • Friends
We sailed on America2 for their February Wreckers Race. What an idyllic afternoon on the water on a beautiful sailing ship. America 2 was comfortable and although there was only a slight breeze she cut through the water beautifully and provided a great sailing experience. Crew could not have been more accommodating. Food and beverages aplenty! It was a great intro to sailing for our friends and reminded us why we love sailing so much. Oh and we won the Race!!!
Written February 26, 2024
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.
John, thank you for booking a Wreckers Race sail with us and taking some time to leave a review. We are happy to hear that you were able to enjoy a beautiful afternoon with our friendly crew and access to ample food and drinks to complete the experience. It is always nice to participate in a winning race, especially as an introduction for friends. We hope to have a chance to welcome you back aboard again any time that you need another reminder of how much you love to sail! - Classic Harbor Line Key West
Written February 27, 2024
This response is the subjective opinion of the management representative and not of Tripadvisor LLC.

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Classic Harbor Line - All You Need to Know BEFORE You Go (2024)