Classic Day Sails or Key West Sunset Sails for 2 or 4 People at Classic Harbor Line: Key West (Up to 21% Off)

Classic Harbor Line

Value Discount You Save
$110 19% $21
Give as a Gift
Limited quantity available
Over 360 bought

In a Nutshell

Outstanding captains and crew dole out royal-treatment service to customers aboard well-maintained sailing vessel

The Fine Print

Promotional value expires May 1, 2018. Amount paid never expires. Subject to availability. Merchant's standard cancellation policy applies (any fees not to exceed voucher price). Limit 2 per person, may buy 2 additional as gifts. Valid only for option purchased. Must be 21 or older with valid ID to consume alcohol. Online reservation required. Valid during sailing season from November 5-May 1. Merchant is solely responsible to purchasers for the care and quality of the advertised goods and services.

After purchasing this deal, you will need to visit the website listed on your Groupon voucher to complete redemption.


Choose from Four Options

  • $89 for Classic Day Sail with beer and wine for two ($110 value)
  • $175 for Classic Day Sail with beer and wine for four ($220 value)
  • $135 for Key West Champagne Sunset Sail for two ($170 value)
  • $269 for Key West Champagne Sunset Sail for four ($340 value)

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

The captain took us out into the open water. If you get seasick easily, it might not be the best. The staff was amazing! Cheese and vegetables and shrimp were served along with unlimited wine a beer. My husband and I thoroughly enjoyed this!
Kate H. · September 10, 2017
We had a wonderful time! The crew was fantastic! The boat was beautiful. My husband and I are so glad we did this.
Beverlee B. · June 22, 2017
Beautiful boat with a great crew. We had perfect weather which made for a wonderful sunset sail. I would recommend this to anyone who wants to see a Key West sunset on the water.
Ethan W. · June 4, 2017

By purchasing this deal you'll unlock points which can be spent on discounts and rewards. Every 5,000 points can be redeemed for $5 Off your next purchase.