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Classic Harbor Line

202 William St, Key West, FL 33040-6645
+1 305-293-7245
Gratuity recommended at entry.
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from US$ 59
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Classic Day Sail Aboard America 2.0
from US$ 91
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Key West Sunset Sail Aboard Schooner 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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Hours Today: 07:00 - 00:00
202 William St, Key West, FL 33040-6645
+1 305-293-7245
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Reviews (1,029)
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331 - 340 of 1,016 reviews

Reviewed 16 November 2016

The Captain and crew were warm friendly and fun. They were very professional and personable. Absolutely loved the sunset cruise aboard a beautiful schooner. Cheers to Capt. Andrew and his crew!

Review collected in partnership with this attraction
Thank timbrowning123
Reviewed 16 November 2016

The staff on board was very knowledgeable, friendly. Captain was awesome! Highly recommend this cruise it was very informative. It was when the boat races were going on in Key West. So we got to see a lot of fancy yachts

Review collected in partnership with this attraction
Thank mjm277
Reviewed 15 November 2016

This was my second sail with Classic Harbor Line. The first was in Boston in June! We had such a great time there, that we were excited to find the same top notch experience in Key West! Fantastic service from the hardworking crew!

Review collected in partnership with this attraction
Thank Laurie K
Reviewed 15 November 2016 via mobile

Captain Heather and her crew did an excellent job! The crew kept us safe, hydrated and very Google conversations. Sail was wonderful with a great full moon, light tropical breeze and great company. I highly recommend this!!

Thank Andrea' V
Reviewed 13 November 2016 via mobile

We took my husband's father in law on this sail for his 82 birthday, and we all thoroughly enjoyed this excursion except my mother in law who fussed about getting wet. While we were out, a front blew through, and we got some sprinkles in...More

Thank Karol A
Reviewed 13 November 2016

GREAT cruise, will definitely recommend it and do it again in the future. Employees were not only courteous but friendly as well.

Review collected in partnership with this attraction
Thank Sue K
Reviewed 12 November 2016

Went with my brother and sister in law for afternoon cruise. The crew was hard working and very friendly. We had a great time. Highly recommend the cruise.

1  Thank c0r0se
Reviewed 11 November 2016

Looking for a last minute sunset sail trip while in Key West, and found this one in front of Schonner's Wharf. Had a great time and there was a great sunset that day, alcohol is plentiful, however the snacks are minimal, plan on a meal...More

Thank Will&Michelle
Reviewed 11 November 2016

Had a blast! Fun time on the water with a very capable crew taking care of our needs. They had beer and wine with some snacks available.

Review collected in partnership with this attraction
Thank R9681IHchrish
Reviewed 10 November 2016

My friend and I were waiting for another day trip when we found this gem! It was a beautiful ship and very inexpensive. The trip is all you can drink and eat snacks while you sail past the sunset! I will be going again the...More

Thank Dpanzeter
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Questions & Answers
Rachel S
26 March 2017|
Answer Show all 3 answers
Response from rwalk89 | Reviewed this property |
25 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.