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Classic Harbor Line

202 William St, Key West, FL 33040-6645
+1 305-293-7245
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Key West Sunset Sail Aboard Schooner America 2.0
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Classic Day Sail Aboard America 2.0
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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.
  • Excellent91%
  • Very good6%
  • Average1%
  • Poor1%
  • Terrible1%
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“sunset sail” (151 reviews)
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Hours Today: 07:00 - 00:00
202 William St, Key West, FL 33040-6645
+1 305-293-7245
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Reviews (1,030)
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11 - 20 of 1,017 reviews

Reviewed 6 May 2017

We booked on a whim and were so glad that we did. The boat was not crowded, the trip was beautiful and relaxing, the wine was flowing, and the crew was delightful. All in all, the most important takeaway, we thought this was a great...More

Review collected in partnership with this attraction
Thank joel g
Reviewed 5 May 2017

The crew was very good and attentive. The captain was skilled. The beverage selection was also very good. Very enjoyable.

Review collected in partnership with this attraction
Thank stevewO1994ZM
Reviewed 4 May 2017

The sunset cruise on the America 2.0 Schooner was outstanding. The captain and crew were excellent, friendly, informative and took excellent care of the passengers. Great experience

Thank Stirling W
Reviewed 2 May 2017

Food was good, crew was energetic and attentive. We especially enjoyed seeing how the crew worked together to raise and lower the sails. Nice to see strong young women working along side the guys. Sunset was absolutely amazing.

Review collected in partnership with this attraction
Thank Deborah C
Reviewed 1 May 2017

We set sail on Saturday the 29th. Captain Andrew and crew of two very professional and hard working woman ( sorry I forgot your names). We had a blast the drinks and snacks were great, several varieties of beer and wine. Also shrimp cocktail and...More

Thank Sean S
Reviewed 29 April 2017

The America 2.0 sunset cruise was nearly perfect. As we pulled out of the harbor, most of the other sunset cruises had music blaring. We put up the sails and it was the wind and the sea, the sun and a cold beer. The sun,...More

Thank WillC599
Reviewed 29 April 2017 via mobile

There's a lot of sunset sailings (and more than a few 'booze cruises') in Key West. We've been on most of them over the years. But for a real sailing experience and great service - Schooner America is the best. A newer, beautiful, state of...More

Thank shark4rae
Reviewed 28 April 2017

Great experience on this sail. Booking on line was efficient and precise. Greeted at port and checked in. Crew and Captain were professional, accommodating, yet humorous! We were offered opportunity to steer, to gain information, and to relax and enjoy. Drink and snacks were offered...More

Thank kittykat12816
Reviewed 27 April 2017

A beautiful ship, a great crew, fun talking with everyone around us and the views simply can't be beat. Worth every penny, and a million photos to prove it

Review collected in partnership with this attraction
Thank Jeffrey J
Reviewed 27 April 2017

Excellent captain and staff, very professional Would definetly go again on this sailing cruise . Quiet no loud music playing

Review collected in partnership with this attraction
Thank Maria W
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Questions & Answers
Rachel S
26 March 2017|
AnswerShow all 3 answers
Response from rwalk89 | Reviewed this property |
24 January 2017|
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
Mark Z
12 January 2016|
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.