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Classic Harbor Line

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Address: 202 Williams Street, Key West, FL 33040
Phone Number: 305-293-7245
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7:00 am - 12:00 am
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Hours:
Sun - Sat 7:00 am - 12:00 am
Description: Classic Harbor Line, operating renowned day sail operations in Newport...
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.
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TripAdvisor Reviewer Highlights

Read all 415 reviews
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  • 386
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  • 26
    Very good
  • 2
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Classy sail, America 2.0 wins again!

We had the best time ever. Perfect sunset sail. So classy and sophisticated. Way better than any of the over crowded party boats. I will never forget this.

5 of 5 starsReviewed March 30, 2015
Bd28t
,
Rapid City, South Dakota
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415 Reviews from our TripAdvisor Community

Date | Rating
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English first
Rapid City, South Dakota
2 reviews
5 of 5 stars Reviewed March 30, 2015 NEW

We had the best time ever. Perfect sunset sail. So classy and sophisticated. Way better than any of the over crowded party boats. I will never forget this.

Was this review helpful? Yes
Homer Glen, Illinois
1 review
5 of 5 stars Reviewed March 30, 2015 NEW

We were going to do the glass bottom boat but no seats available....walked along boardwalk and saw this gorgeous sailboat and it looked like they were boarding. Decided to try it and so glad we did. The crew were so nice...what a bargain...beautiful weather, wonderful day...money well spent. Will do it again in a minute. Such an awesome day.

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Nassau, New Providence Island
Top Contributor
51 reviews 51 reviews
4 attraction reviews
36 helpful votes 36 helpful votes
5 of 5 stars Reviewed March 25, 2015

BEST Sail ever! The other Trip Advisor reports of 5-star experiences were correct! Based on TA we picked the BEST sail ever!! At the ticket booth the cashier was calling the crew to see if they had any non-caffeine soft-drinks onboard. When she heard they didn’t she WENT to the STORE HERSELF to buy some for ONE PERSON who had... More 

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1 review
1 helpful vote 1 helpful vote
5 of 5 stars Reviewed March 19, 2015

We have sailed KW schooners and if you want a true sailing experience with people who know sailing, America 2.0 is the only one! Izzy and Mary

Was this review helpful? Yes 1
Lorain, Ohio
1 review
5 of 5 stars Reviewed March 13, 2015

Loved the "Wrecker's Race" on the America 2.0. Captain and crew were very friendly, efficient and helpful. Allowed anyone who wanted to help with 'raising the sails'. Kept the thirst at bay with seemingly unending adult beverages. Of course we won, even with a 9 minute handicap, kudos to the skilled Captain and crew. Would highly recommend this adventure to... More 

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Prior Lake, MN
Top Contributor
66 reviews 66 reviews
16 attraction reviews
45 helpful votes 45 helpful votes
5 of 5 stars Reviewed March 7, 2015 via mobile

Couldn't have been better. Fun ride, crew was attentive and great. The boat is clean and beautiful. It was a beautiful route and the day was a nice break from all the spring breakers In town. The boat is big and smooth and easy to move around in and find shade if needed

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Arlington, Texas
Senior Reviewer
8 reviews 8 reviews
4 attraction reviews
5 of 5 stars Reviewed March 6, 2015

My husband and I had a marvelous time on this cruise as we watched the crew engage passengers in raising the sails so we could set off and then provided us with a wonderful selection of cheeses, shrimp, crackers, fruit and LOTS to drink. The evening was perfect and the sunset magnificent. We had fun making new friends from St... More 

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Austin, Texas
Top Contributor
91 reviews 91 reviews
21 attraction reviews
65 helpful votes 65 helpful votes
5 of 5 stars Reviewed March 5, 2015

Great crew! Great Captain! We were on the America 2.0 with a little over 20 other passengers. Two hour cruise out to blue water just passed the reef. Perfect weather and just fun being on board. Did not feel like an intruder on someone else's vessel or that we were in the way or anyone was having too much or... More 

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Rochester, NY
Senior Contributor
42 reviews 42 reviews
11 attraction reviews
20 helpful votes 20 helpful votes
5 of 5 stars Reviewed March 4, 2015

The America 2.0 is a sleek black beauty of a schooner that will take you out into the magnificent waters off Key West on a sailing experience you will never forget. My wife, I and another couple had high expectations for this sunset cruise after reading TripAdvisor reviews. We were not disappointed! The crew, Captain Ron, Kelly, Heather, all onboard... More 

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1 review
5 of 5 stars Reviewed March 4, 2015 via mobile

Superb sailing experience. Beautiful boat. Great crew. Generous offerings of wine, beer, shrimp and snacks. Would have sailed again (20% discount) if had been earlier in stay. Romantic and classy.

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Typical questions asked:
  • Will you pick up and drop off at my hotel?
  • I have a family of 7. Can your tour accommodate all of us together?
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