Boston, MA

Schooner Adirondack III

Schooner Adirondack IIISet sail aboard the first yacht of the Classic Harbor Line Fleet in Boston: Schooner Adirondack III! This 80-foot beauty has been setting sail, making waves, bonding friends, families, and lovers in Boston since 2013! She has numerous repeat guests every summer and is out for a sail up to 4 times a day! Drinks are always available for purchase and the captain and crew are always friendly and fun. (Just read her awesome reviews!) And take a look at her many sails offered listed below…

The best way to do some sightseeing in Boston Harbor is on this beautiful sailboat.  Glide through the water with grace and speed and enjoy an afternoon under the sun aboard a Boston sailing adventure.  

Boston Day Sail

Within minutes of leaving the dock, you’ll forget the distractions of life on land, as you experience the joy of a leisurely sailing cruise. Our classic afternoon day sails are the perfect way to see the sights of Boston Harbor. There is no better way to enjoy the day than sailing aboard the schooner Adirondack III, which is the most elegant sailing excursion you will find in the harbor. Adirondack III is a classically styled 80-foot pilot schooner with long sleek lines. She is smooth and gentle sailing vessel with some speed.

  Duration: 2 hrs   Boat: Adirondack III   Cost: $45

Boston Sunset Sail

Experience a beautiful Boston Harbor sunset on the water and see some of the city’s waterfront landmarks as the sun dips below the horizon. Sailing offers a smooth and gentle experience on the water, which is great for having a romantic early evening out with that special someone. Our crew and captain offer top notch customer service to our guests.

  Duration: 2 hrs   Boat: Adirondack III   Cost: $55 - $57

Boston City Lights Sail

For the ultra-romantic choose our City Lights Sail aboard our sailboat. This serene sail allows you to experience Boston with peaceful tranquility. Enjoy the evening sea breeze swirling around you and all of Boston’s twinkling lights as your backdrop. Take-in the shimmering city of Boston on a smooth and gentle sail. Blankets are available to guest upon request on chilly nights. Cozy up with a loved one on the decks of our beautiful schooner.

  Duration: 1.5 hrs   Boat: Adirondack III   Cost: $40

Boston USS Constitution Turnaround Sail

U.S.S. Constitution Turnaround Sail aboard Schooner Adirondack III

U.S.S. Constitution Turnaround Sail aboard Schooner Adirondack III. Join us for the 3-4 hour long, July 4th turnaround cruise of the U.S.S. Constitution, the oldest (1797) actively commissioned naval vessel in the world. Experience this yearly event like you never have before aboard Adirondack III, a classic 80-foot pilot schooner. She features comfortable seating and a brisk ride, as we are able to view the turnaround of the U.S.S. Constitution.

  Duration: 3 hrs   Boat: Adirondack III   Cost: Adults $125 | Child $100

Labor Day Fireworks Cruise Aboard Adirondack III

What better way to celebrate the end of summer, but with a stellar fireworks display from the waters of Boston Harbor? Join us aboard beautiful Adirondack III for a magnificent Labor Day cruise. This 1.5-hour cruise offers guests the opportunity to soak up Boston’s colorful fireworks display from an awesome vantage point, practically right underneath them and out on the water! (The event does not sail and offers spectacular views of the fireworks)

  Duration: 2 hrs   Boat: Adirondack III   Cost: $75

Harborfest Fireworks Aboard Adirondack III

Get the fourth of July weekend started with a BANG! Step aboard the Adirondack III for a spectacular fireworks display on Boston Harbor.  Join us for two hour and thirty minute sail & cruise, followed by Harborfest Fireworks lighting up along Boston’s Waterfront.
In addition to a fantastic experience, this captivating Labor Day Fireworks Cruise will feature delicious, complimentary desserts, cheese and flatbreads, and sliced fruits, water and soda.

  Duration: 2.5 hrs   Boat: Adirondack III   Cost: Adults $75 | Child $50

Winthrope Fireworks Cruise with Classic Harbor Line

Winthrop 4th of July Fireworks Cruise and Sail on Adirondack III

Don’t want to deal with all the traffic crowds and hype surrounding the 4th of July, but still want to celebrate and enjoy the patriotic holiday? Step aboard the Adirondack III for a cruise to Winthrop to watch the fireworks and then sail back to Boston at the end. Sip on Champagne and enjoy this magical evening with the best seats in the house! 

  Duration: 3 hrs   Boat: Adirondack III   Cost: Adult $75 | Child $50