We noticed that you're using an unsupported browser. The TripAdvisor website may not display properly.
We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox. Mac: Safari.
All 309 Key West Attractions »

Classic Harbor Line

202 Williams Street, Key West, FL 33040
305-293-7245
Ranked #5 of 173 tours in Key West
5.0 of 5 stars 154 Reviews
Book Now

Type: Tours
Owner description: Dedicated to providing the most perfect hospitality and sailing experience one could find in Key West, Classic Harbor Line hopes for the privilege of...... more » Owner description: 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 vessel in the local schooner fleet: Adirondack III and America 2.0 Both classic schooner sails – a mimosa morning sail, a day sail or sunset sail – is known to be the quintessential Key West activity that will highlight your stay and be the lasting memory forever. « less
Useful Information: Activities for older children
Update attraction details
Write a Review

154 reviews from our community

Visitor rating
    144
    10
    0
    0
    0
Date Rating
Key West, Florida
1 review
5 of 5 stars Reviewed May 23, 2012 NEW

Went out for the afternoon sail on the Adirondack III and found it too be a lovely way to spend an afternoon. The boat was beautiful and the crew was friendly and helpful. I'd highly recommend. More

Was this review helpful? Yes
2 reviews
5 of 5 stars Reviewed May 19, 2012

I can not believe how awesome this company is. Steven was the one who hooked us you'll probably find him hanging out by the boat! Ask him or don't ask him to take picture of the boat either way he will invite you to do so! The staff is very knowledgeable of the history of the Adirondack III. After encountering... More

Was this review helpful? Yes
Florida
Top Contributor
73 reviews 73 reviews
Reviews in 37 cities Reviews in 37 cities
140 helpful votes 140 helpful votes
5 of 5 stars Reviewed May 13, 2012
1
person found this review helpful

What better way to spend a couple hours than “on the water” under sail. A great crew sails the fastest schooner in Key West, the Adirondack III. It’s a beautiful boat and comfortable as you can sit on cushions around the cockpit. The morning cruise features mimosas for $1; the sunset sail offers champagne and shrimp cocktail. They guide the... More

Was this review helpful? Yes
New Lenox, Illinois, United States
Contributor
14 reviews 14 reviews
5 of 5 stars Reviewed May 12, 2012

I've been on several sailboats in the Key West area. I really can't complain much about any of them, because so far they've all been great! However, I went on the Adirondacks sunset cruise on May 6th, 2012 and had such a great time. The crew was all really friendly, helpful, and informative. The ride was smooth and calming, very... More

Was this review helpful? Yes
Whetstone, AZ
Senior Reviewer
7 reviews 7 reviews
1 helpful vote 1 helpful vote
5 of 5 stars Reviewed May 11, 2012
1
person found this review helpful

Wonderful experience. Very knowledgeable and friendly crew. Beautiful ride after two days of rain. Very peaceful and serene. Great way to end a visit to Key West. More

Was this review helpful? Yes
Charlottesville, VA
Reviewer
5 reviews 5 reviews
16 helpful votes 16 helpful votes
5 of 5 stars Reviewed May 9, 2012
1
person found this review helpful

My husband and I booked this trip on a whim and we're so glad we did. It was fun, informative, and relaxing, and of course the sunset always looks better from a sailboat! The captain and crew were great. We even got to help raise the sails as we headed out (note that you get a free drink if you... More

Was this review helpful? Yes
Syracuse, New York
Reviewer
5 reviews 5 reviews
3 helpful votes 3 helpful votes
5 of 5 stars Reviewed May 6, 2012
2
people found this review helpful

A sunset sail is big business in Key West. Too many of the boats "motor-sail". The sails are up, but they use their motors. This is NOT the case in the Adirondack! When we went out, a front had come through, the wind was piping and the sail was fantastic! The Captain and crew were very knowledgeable and personable. Try... More

Was this review helpful? Yes
Wilmington, Delaware, United States
2 reviews
5 of 5 stars Reviewed May 3, 2012

We took a two hour sailing trip on the America 2 and had a great time. This is a new 105 foot schooner that is built in the traditional style of sail boats of long ago, but with modern amenities. This boat is fast! We had good wind and really enjoyed sailing to the end of Key West and back. More

Was this review helpful? Yes
Key West, Florida
Top Contributor
64 reviews 64 reviews
Reviews in 16 cities Reviews in 16 cities
28 helpful votes 28 helpful votes
5 of 5 stars Reviewed May 3, 2012

Great few hours sail with a really wonderful and professional crew. The boat was beautiful and so well maintained. We sailed in the 2012 Wreckers Race. The good news is that the Adirondack III is in Key West all year round, while so many of the other sailing vessels leave to run trips north in the summer. More

Was this review helpful? Yes
Sarasota, Florida
Senior Reviewer
6 reviews 6 reviews
5 helpful votes 5 helpful votes
5 of 5 stars Reviewed May 2, 2012

We booked a morning Mimosa sail. It was to last for 1.5 hours and cost $35 dollars. I can only say that this was the best use of my travel money ever!!! We sailed upon the Adirondack III and enjoyed a warm, breezy sail. The Captail and Crew were competent and extremely attentive. Our glasses were never empty unless we... More

Was this review helpful? Yes

Travelers who viewed Classic Harbor Line also viewed

SUP Key West
5 of 5 stars 97 Reviews
Key West, Florida Keys
Schooner Jolly II Rover
5 of 5 stars 151 Reviews
Key West, Florida Keys
 
Easy Day Charters
5 of 5 stars 173 Reviews
Key West, Florida Keys
Pepe\
5 of 5 stars 70 Reviews
Key West, Florida Keys
 

Been to Classic Harbor Line? Share your experiences!

Write a Review Add Photos Add Videos

Owners: What's your side of the story?

If you own or manage Classic Harbor Line, register now for free tools to enhance your listing, attract new reviews, and respond to reviewers.

Manage your listing
See all sites
Cruise Critic

The ultimate cruise resource: cruise reviews, deals, news and advice.

SeatGuru

The world's most comprehensive source for airline seats, airline info, & in-flight amenities.

Family Vacation Critic

The best family vacations start here.

Best beach houses of 2012 »