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Holiday Cruises

Holiday CruisesGet into the Holiday spirit and join us for a Boston holiday cruise or Boston harbor boat ride. Classic Harbor Line offers a number of events throughout the year that help celebrate our national holidays.  Memorial Day, 4th of July, Labor Day, New Years Eve, and the holiday month of December!  Winter in Boston can be cold but the Yacht Northern Lights embraces an intimate, cozy atmosphere which will get you into the holiday spirit.  Grab your friends and family to join us on a Boston Harbor Holiday Cruise and enjoy a “Irish Christmas Carol”, “Cocoa and Carols”, “Holiday Jazz” and more! Cruise through Boston Harbor at night and see the city light up with the twinkling lights the skyline has to offer.  Sing along and sip on a special holiday drink and enjoy the evening out on the water with us.  Join us on these Boston Harbor cruises to celebrate and share with a loved one.

Small Holiday Office Party Options | Starting at $300/Table on public events
Classic Harbor Line offers festive holiday cruises almost every night during the holiday season.  You can book a table aboard Northern Lights (for up to 2-8 guests per table) on a Sunset Cruise, Harbor Island Cruise, or Caroling Cruise, starting at $300/table. You can customize your party with special catering or bar packages with an event sales agent:[email protected] 617-951-0020.
*10% discount on booking 4 or more tables.


Boston Harbor Labor Day Fireworks Cruise

Labor Day Fireworks Cruise

Get front row seats to Boston Harbor’s Labor Day Fireworks Cruise aboard Northern Lights, a classic 1920s style commuter yacht. Celebrate the last days of summer with friends and family. Watch the fireworks from the best seats in the harbor, right underneath them!

  Depart: Rowes Wharf   Boat: Northern Lights   Cost: $50

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

Boston Music Cruise: An Irish Christmas Carol

An Irish Christmas Carol

Take to the water and get into the holiday spirit with Slainte, our house Irish band, and sing some merry holiday ballads the way the Irish do, with a beer in hand and a whiskey or two. It’s the holidays and with our 1920’s styled motor yacht, Northern Lights, decked out with festive décor and the sound of the holidays in the air, this unique Boston Music Cruise is sure to put you in a merry spirit! Tasty holiday adult beverages are also available on our Boston Music Cruise:  An Irish Christmas Carol cruise. Take a cruise with friends to celebrate the season or choose this event for your holiday company party.

  Depart: Rowes Wharf   Boat: Northern Lights   Cost: $44

Boston Holiday Jazz Cruise

Holiday Jazz Cruise

Step aboard our luxury Yacht Northern Lights in full holiday decor and join us for our romantic Holiday Jazz Cruise. Enjoy this 1.5 hour cruise with your loved one and a glass of Champagne in hand or spiked hot cocoa. See the city lights twinkle at night as you cozy up for an evening out in Boston Harbor aboard a luxury yacht.  Tasty holiday adult beverages are also available on our Holiday Jazz Cruise. Take a Boston Harbor cruise with friends to celebrate the season, entertain out-of-town family, or choose this event for holiday company party.  This is a perfect way to get into the Holiday spirit!  

  Depart: Rowes Wharf   Boat: Northern Lights   Cost: $44

Boston Holiday Cruise

Cocoa & Carols Holiday Cruise

Step aboard our luxury Yacht Northern Lights in décor for the holidays and set sail for an evening of caroling through Boston Harbor. This is a Boston Holiday Cruise that you cant miss out on.  Join in on live Holiday Carols conducted by Tim McHale of the Boston Minstrels and get into the holiday spirit with friends and family. While singing may or may not be your thing, we also have delicious hot cocoa, cookies, and treats for all our guests. Sit back and enjoy the gorgeous view of Boston from the heated salon of Northern Lights, a 1920’s styles New England Yacht, and get into the Holiday Spirit on this Boston Holiday Cruise. Classic Harbor Line also offers a live Holiday Jazz Trio and Irish Christmas Carolers! (Musically-talented groups are our special hosts for each of our Holiday cruises!)

  Depart: Rowes Wharf   Boat: Northern Lights   Cost: $44