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Holiday Cruises

Holiday CruisesClassic Harbor Line offers a number of events throughout the year that help celebrate our national holidays. From the most major harbor event — Boston Harbor for the Boston Fireworks, to our own special holiday season themed cruises, “Cocoa & Carols” (Coming Soon), you are sure to find a special offering monthly within our fleet. Join us on these Boston Harbor cruises to celebrate and share with a loved one. Boston holiday cruises are the best way to view the beautiful city that we proudly call home.

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: privatecharters@boston-sailing.com or 617-951-0020.
*10% discount on booking 4 or more tables.


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

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

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

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 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

Irish Christmas Carol in Boston

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 tour is sure to put you in a merry spirit! Tasty holiday adult beverages are also available on our 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 cruise with friends to celebrate the season, entertain out-of-town family, or choose this event for holiday company party.

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

Boston Cocoa and Carols 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. 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. 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

Boston New Year's Eve Cruise

Boston Harbor New Year’s Eve Cruise

Step aboard our luxury Yacht Northern Lights in full holiday decor and join us for a romantic, fun, and tasteful cruise in Boston Harbor for the New Year’s Eve Fireworks display. Enjoy this 3-hour cruise with your loved ones and a glass of champagne in hand as we celebrate the New Year. Start the night out with lights appetizers from our stationary or passed hors d’ oeuvres or head upstairs to the Aurora Room, and memorialize you first moments of the New Year in our photo booth. Take as many photos as you wish! Photos and catering are included with your ticket aboard our cruise. Farm to Table Display: Cheese Wedge Platter with Fresh and Dried Fruits, Grilled Seasonal Vegetables, Green goddess dip and roasted red pepper humus, Bruschetta Duo: Sweet Pumpkin & Ricotta, Herbed Chick Pea and Pancetta, and Flat Breads. Passed Appetizers: Petite Filet Crostini, Coconut Crusted Chicken Skewers, Savory cones with Garlic Humus and Balsamic Microgreens, and Raspberry & Brie Phyllo Triangles. Visit our bar located on the main deck to buy adult beverages including champagne! Bottles of Moet & Chandon can be pre-purchased online while buying tickets. After the photos are snapped (unlimited), dance the night away with our house Jazz Band which will be playing top New Year’s Eve hits from the last 40 years.
  Depart: Rowes Wharf   Boat: Northern Lights   Cost: Adults Only (21yrs up) - $165