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Classic Harbor Line

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Address: 202 Williams Street, Key West, FL 33040
Phone Number: 305-293-7245
Website
Today
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 423 reviews
Visitor rating
  • 393
    Excellent
  • 27
    Very good
  • 2
    Average
  • 1
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  • 0
    Terrible
Perfect evening

We have done the sunset cruise on the America II twice now and each time was perfect. We took our entire family, 13 of us, daughters, husbands, and 7 grandkids from 20yrs old down... read more

5 of 5 starsReviewed May 14, 2015
Sharon W
,
North Conway, New Hampshire
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423 Reviews from our TripAdvisor Community

Date | Rating
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English first
New Cumberland, Pennsylvania, United States
Top Contributor
76 reviews 76 reviews
34 attraction reviews
25 helpful votes 25 helpful votes
4 of 5 stars Reviewed May 25, 2015

My husband and I signed up for an afternoon sail cruise and it was fabulous. The weather was perfect. It was about 2-2 1/2 hours in length. Many different types of beverages were served. It was a very enjoyable time. Maybe next time we'll do a sunset cruise.

Was this review helpful? Yes
North Conway, New Hampshire
1 review
5 of 5 stars Reviewed May 14, 2015

We have done the sunset cruise on the America II twice now and each time was perfect. We took our entire family, 13 of us, daughters, husbands, and 7 grandkids from 20yrs old down to 8 yrs old last year as the final night of a week long birthday celebration for my husband's 70th birthday. It was wonderful. The kids... More 

Was this review helpful? Yes
Woking, United Kingdom
Reviewer
5 reviews 5 reviews
6 helpful votes 6 helpful votes
5 of 5 stars Reviewed May 5, 2015

After a very wet day in Key West (it actually flooded) we were surprised it actually sailed lots of people did not turn up and only four us actually boarded, we were treated to a great evenings sailing we all had a good chance of steering and the two lads helped hoist the sails. The crew cannot do enough for... More 

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Hartford, Connecticut
1 review
2 helpful votes 2 helpful votes
5 of 5 stars Reviewed May 1, 2015

We had a wonderful, relaxing sunset cruise on the schooner America 2.0. The cost of the trip included hors d'oeuvres and drinks and a chance to steer the boat. The crew was friendly and attentive. The cruise was everything we wanted.

Was this review helpful? Yes 2
Chicago, Illinois
Senior Reviewer
7 reviews 7 reviews
3 attraction reviews
1 helpful vote 1 helpful vote
5 of 5 stars Reviewed April 25, 2015

The trip on the schooner was relaxing and great to be able to enjoy the power of just the sales. We choose a good day to be out on it. The captain allowed passages to drive the boat while under sail power. The crew was very helpful

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Starkville, Mississippi
1 review
5 of 5 stars Reviewed April 24, 2015

There’s lots to do in Key West, but a sunset sail on the America 2.0 has to be one of the island’s best experiences. The ship was built in 2011, but is a classic sailing vessel. The crew, Stephanie and Heather, and Captain Ron are great at engaging the passengers while carrying out their duties. Wonderful way to experience a... More 

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Chippewa Falls, Wisconsin
2 reviews
2 helpful votes 2 helpful votes
5 of 5 stars Reviewed April 19, 2015

We took a sunset cruise as part of a large group on a sailboat from Classic Harbor Line. As we pulled out, it was quickly realized that we had the perfect vessel, once we saw the others. Other boats had loud, obnoxious music. Fine if that is what you're wanting/expecting. This experience was quiet, relaxing, and it came with all-you-can... More 

Was this review helpful? Yes 2
Santa Fe, New Mexico
2 reviews
5 of 5 stars Reviewed April 6, 2015

Once was not enough. We went twice and next year will for sure go four times. Faster than the others. Pretty. And cheerful staff who will let you help or not as you like - plus serve wine and beer to round out the experience. Really it is terrific!

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Rapid City, South Dakota
2 reviews
2 helpful votes 2 helpful votes
5 of 5 stars Reviewed March 30, 2015

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 1
Homer Glen, Illinois
1 review
1 helpful vote 1 helpful vote
5 of 5 stars Reviewed March 30, 2015

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.

Was this review helpful? Yes 1

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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?
  • How should I dress for this tour?