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Boston, MA

Day Sails/Cruises

Browse By Day Sails and Cruises Get out on the water for some fresh air, some sun on your face and do some Boston sailing. Enjoy a Boston Harbor Day Sail with us aboard one of our classic boats. Whether you sail aboard our sailboat past Fort Independence on Castle Island or circumnavigate Fort Warren on George’s Island, it is a simple way to get away from the mayhem of Boston and take in the sights from the Harbor. The perfect activities that go hand in hand are a Boston sightseeing cruise or sail, and soaking in the sun! Bring a picnic on the sailboat or purchase a snack from the bar aboard our motor-boat. Let our crew serve you a refreshing beverage and within minutes you will experience the simple joys of a leisurely Boston Harbor cruise and forget the distractions of life on land. Whether you are a local looking for an escape or a visitor wanting to do a sightseeing boat ride, you are sure to have a memorable time.


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 Day Sail

90 Minute Day Sail

Our classic, 90-minute, 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 speediness to boot.  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.

 

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

Boston Harbor Island Sightseeing Cruise

Boston Harbor Islands Cruise

Step aboard the Northern Lights for a top-of-the-line sightseeing cruise to discover some of the mysteries behind Boston’s harbor islands. Sit back and relax in our climate-controlled cabin or enjoy the sea breeze on our open top deck. During your harbor cruise with us, our captain will provide narration and crew will be around to assist in making your trip more comfortable.

  Depart: Rowes Wharf   Boat: Northern Lights   Cost: $38

Boston Brunch Cruise

Boston Brunch Cruise aboard Northern Lights

Weekends are a time for relaxing and getting your days started the right way. Join us for a 2.5 hour Mimosa and Bloody Mary Cruise aboard the elegant Northern Lights to jump start your relaxation mode on this Boston Brunch Cruise. While aboard choose from a variety of Mimosas and Bloody Mary’s. Enjoy our gourmet brunch buffet and select a cozy seat aboard Northern Lights as we cruise around Boston Harbor to capture panoramic views of Boston.  This is the perfect event for groups looking to entertain guests from out of town. You can see the sites without giving up a relaxing weekend. We can accommodate small bridal parties or even morning after wedding parties.  The Brunch Cruise offers the perfect event for the individual or the group looking to celebrate and relax.

  Depart: Rowes Wharf   Boat: Northern Lights   Cost: $68

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

One-Hour Inner Harbor Cruise

Take a cruise on the elegant Northern Lights for a glimpse into the glamour of the 1920s. Relax with the sea breeze on one of our top deck benches or chill inside with our climate-controlled, wood trimmed salon. Throughout the cruise, our local captains will share their knowledge and personal stories of growing up in Boston Harbor. Crew will be around to assist pointing out sites and making sure you feel comfortable.

  Depart: Rowes Wharf   Boat: Northern Lights   Cost: $22

Boston Painting Night on a boat in Boston Harbor

Paint Night on Northern Lights

Be inspired by the sea around you as our instructor takes you on an easy step-by-step process to paint the Boston skyline and harbor islands.  Kelli Hamilton, of Ruby Gypsy Paint Party, with southern charm and patience, will guide your creative cruise through Boston Harbor as she demonstrates our featured painting of Boston Light and skyline. You do not have to begin this journey as an artist, but we guarantee you’ll have a great time discovering your creative side paint on the sea on this Boston Cruise. Paint, paint brushes, and your canvas will be provided aboard. Discover your creative side and try out our paint party on the sea.

  Depart: Rowes Wharf   Boat: Northern Lights   Cost: Adult $68