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Boston, MA

Sailing

Browse by SailingJoin us with our professional crew and take to the waters of Boston Harbor. Let our crew dazzle you with their sailing skills and top-notch customer service. Sailing is fun, but sailing and sightseeing is the most wonderful way to experience Beantown. Sail past Boston’s Waterfront to see the U.S.S. Constitution, Fort Independence (named by George Washington), Marriott Custom House Tower, U.S.S Cassin Young, and see the steeple of the Old North Church in Boston’s North End. Enjoy all these sites with a glass of wine in hand aboard our 80-foot schooner, Adirondack III, offering the most premium sailing experience in Boston.


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.

  Depart: Rowes Wharf   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.

  Depart: Rowes Wharf   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.

  Depart: Rowes Wharf   Boat: Adirondack III   Cost: $40

Sails and Ales featuring Harpoon Brewery

Join us for an exciting sunset sail and beer tasting with a local favorite, Harpoon brewery! This is not just sailing with a couple of cold brews in the ice chest, we are taking that one step further by partnering exclusively with Harpoon to bring you a full tasting experience. Whether you’re joining us to decompress after a long day at the office, celebrating a milestone with friends, Sails and Ales aboard schooner Adirondack III with our Harpoon Beer Captain is sure to bring a noteworthy flare to your evening.

  Depart: Rowes Wharf   Boat: Adirondack III   Cost: $55 + $16 (tasting)

Blue Moon Sail

You know the saying, “Only once in a blue moon.” Blue moons happen once every year to every couple of years. However, a second moon in a month during the summer time is much more rare event. The next summer time blue moon shines on Boston Harbor in August of 2021. We look forward to having you join on this this rare special event next time! Check back at a much later date to get ticket and information.

  Depart: Rowes Wharf   Boat: Adirondack III   Cost: $40

Boston Harbor Islands Picnic Sail

Unite on a three-hour sail on our sailing ship, Adirondack III, to discover adventure, learn a bit history, relax, and hear stories of ghosts, battles, and pirates. On our sailing trip through the islands there is a little something for everyone in your group to enjoy. Known for their rich history and peacefulness the Boston Harbor Islands have welcomed vacationers and day trips for hundreds of years. Leave the hectic city behind as we sail past the lush green terrain and catch glimpses of the amazing coastal wildlife. (A gourmet-boxed lunch is included in this excursion.)

  Depart: Rowes Wharf   Boat: Adirondack III   Cost: $76

Boston Harbor Islands Sail

Step aboard the Schooner Adirondack III for a three hour excursion to explore the Boston Harbor Islands by sail. Known for their rich history and peacefulness the Boston Harbor Islands have welcomed vacationers and day trips for hundreds of years. Leave the hectic city behind as we sail past the lush green terrain and catch glimpses of the amazing coastal wildlife. (Lunch is not included with the price of the ticket for this activity)

  Depart: Rowes Wharf   Boat: Adirondack III   Cost: $63

Full Moon Sails

Have you ever experienced the rising of a full moon on the water? We can’t guarantee to watch the full moon rise into the sky, but on some full moons, we get a rare opportunity to watch the giant bright moon climbing above the ocean horizon. And it is literally out of this world and breath-taking to see! Choose a Full Moon Sail to see the moonlight shimmer on the waters of Boston Harbor. Sights are enjoyed from the Adirondack III, which offers a comfortable and relaxing evening cruise with a little speed that is brisk and invigorating.

  Depart: Rowes Wharf   Boat: Adirondack III   Cost: $40

Mother’s Day Picnic Sail

Mothers are special people that have made sacrifices to raise a family. We know that you are busy and so is mom, so take this day as an opportunity to relax with your extraordinary parent on a sail aboard the Adirondack III. Relish in a picnic sail through the Boston Harbor Islands and enjoy a gourmet-box lunch aboard our schooner and relax surround by the peaceful harbor islands. (Unfortunately, in 2016, we will be unable to host a Mother’s Day Picnic Sail due to a scheduling conflict with our NYC office. Please feel free to meet the Adirondack III in NYC for the America’s Cup Trials).

  Depart: Rowes Wharf   Boat: Adirondack III   Cost: $76

Father’s Day Harbor Island Picnic Sail

Grab your Pop for a fun-filled afternoon aboard our schooner with a lunch of fresh fruit, gourmet sandwiches, chips, and dessert as our highly experienced crew and captain take you on a three-hour Boston Harbor Island Picnic Sail. Enjoy this scenic adventure through the islands, which are filled with history from the Revolutionary War all the way through World War II. This sail is sure to impress the Dad that enjoys nature, adventure, relaxing, and history on Father’s Day.

  Depart: Rowes Wharf   Boat: Adirondack III   Cost: $76

Boston USS Constitution Turnaround Sail

USS Constitution Turnaround Sail

Once a year the USS Constitution heads out of the harbor to Fort Independence for a 21-gun salute. Sail along side our oldest operating warship used to train sailors in the US Navy as she cruises through Boston Harbor. Folks line the shoreline to watch the Constitution on one of her rare trips, get front row seats on the schooner Adirondack III as we escort our brave ship down to Fort Independence. (Unfortunately, the USS Constitution is at dry dock until 2018. Check back for tickets to watch the Turnaround Sail in spring of 2018.)

  Depart: Rowes Wharf   Boat: Adirondack III   Cost: $125

Boston Harbor Islands Memorial Day Sail

Step aboard the sailboat Adirondack III for a three-hour picnic excursion to explore the Boston Harbor Islands by sail on Memorial Day. Known for their rich history and peacefulness the Boston Harbor Islands have welcomed vacationers and day trips for hundreds of years. Leave the hectic city behind as we sail past the lush green terrain and catch glimpses of the amazing coastal wildlife.

  Depart: Rowes Wharf   Boat: Adirondack III   Cost: $76

Winthrope Fireworks Cruise with Classic Harbor Line

Winthrop 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. 

  Depart: Rowes Wharf   Boat: Adirondack III   Cost: 65.00

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 a two cruise, followed by a sail to watch the Harborfest Fireworks light up along Boston’s Waterfront.

  Depart: Rowes Wharf   Boat: Adirondack III   Cost: $65

July 4th Fireworks

Join us aboard the historic and beautiful Adirondack III for a magnificent 4th of July Cruise and see why no other Independence Day event compares! While aboard, get a crowd-free view of Boston’s stellar fireworks display from the waters of Boston Harbor. (This event does not sail and can only offer an obstructed and distant view of the fireworks.)

  Depart: Rowes Wharf   Boat: Adirondack III   Cost: $100

Boston Harbor Island Labor Day Sail

Looking for a special way to celebrate Labor Day this year? Join us on a three-hour sail on our sailing ship, Adirondack III to discover adventure, learn some history, relax, and hear stories of ghosts, battles, and pirates. On our sailing trip through the islands there is a little something for everyone in your group to enjoy. Known for their rich history and peacefulness the Boston Harbor Islands have welcomed vacationers and day trips for hundreds of years. On your day off, leave the hectic city behind as we sail past the lush green terrain and catch glimpses of the amazing coastal wildlife. (A gourmet-boxed lunch is included in this excursion.)

  Depart: Rowes Wharf   Boat: Adirondack III   Cost: $75

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)

  Depart: Rowes Wharf   Boat: Adirondack III   Cost: $75