Classic Harbor Line

Classic Harbor Line

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In a Nutshell

Passengers board a replica of the original America’s Cup winner for day sails past Key West landmarks or sunset cruises with champagne

The Fine Print

Promotional value expires Apr 22, 2016. Amount paid never expires. Reservation required. Merchant's standard cancellation policy applies (any fees not to exceed Groupon price). Limit 2 per person, may buy 2 additional as gifts. Valid only for option purchased. Valid for dates listed on website for day sail. Must be 21+ to consume alcohol. Everyone must have a ticket to board. Merchant is solely responsible to purchasers for the care and quality of the advertised goods and services.

Choose from Four Options

On the classic day sail, passengers board the America 2.0, a replica of the first schooner to win the America’s Cup in 1851. Throughout the two-hour excursion, groups will see landmarks including Fort Zachary Taylor and the Sand Key Lighthouse, and perhaps even some dolphins and sea turtles.

America 2.0 also serves as the vessel for the champagne sunset sail, its mahogany-fitted deck an elegant complement to the romantic, two-hour cruise. In addition to champagne, passengers can also help themselves to complimentary cheese, crackers, and shrimp cocktail.

Classic Harbor Line

With four locations along the Eastern seaboard, Classic Harbor Line offers unobstructed views of Boston, Manhattan, Newport, and Key West with its throwback fleet of sailboats and classic yachts. Passengers hop aboard for day trips, private charters, and special events on water set against anything from a glowing sunset to a resplendent city skyline.

Modeled after 1890s schooners, the Boston outpost's 80-foot, 41-passenger flagship, Adirondack III, uses its long, lean shape to easily cut through any waves or schools of fish paparazzi. Meanwhile, the ship's former port of Key West now boasts an even longer vessel: the 105-foot America 2.0, a replica of the original schooner that won the America's Cup in 1851. Each location also tends a fleet of smaller crafts as well, each reservable for enjoyable marine jaunts complete with ample seating, shade, and smiling crew members.

Customer Reviews

Great experience! Highly recommend!
Matthew L. · December 22, 2016
The staff is wonderful. Ask the Captain if you can take a turn at the helm!
Dave S. · April 25, 2016
Excellent service sservice from wonderful friendly staff. A magical sail on a magnificent old schooner.
Roy D. · April 24, 2016
Merchant Location Map
  1. 1

    Classic Harbor Line

    202 Williams St.

    Key West, FL 33040


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