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Boston, MA

Romantic Sails/Cruises

Romantic CruiseTake to the water and fall in love all over again. There are a lot of romantic things to do in Boston, but stepping aboard one of our classic vessels for an unforgettable memory is by far the most romantic.
Take a deep breath and relax with the feeling of the wind in your hair. Sip on champagne and have a quiet, intimate conversation with your loved one as you drift through Boston Harbor. Sit aboard one of our yachts and have moments of laughter and take in the breath taking views. Whether it is a City Lights Cruise or Sunset Sail you and your loved one will share an experience that will last a lifetime and you are sure to make this a regular date idea.


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

Romantic Boston Sunset Cruise

Boston Sunset Cruise

Join us for an after work cruise to relax with friends and watch the sky as it changes from blues to oranges behind the outline of Boston’s city skyline. Experience a sunset cruise departing from bustling Rowes Wharf and head out to watch the sun go down over the city of Boston. Bring a date or meet a group of friends aboard the classically styled yacht, Northern Lights. Cruise by the U.S.S. Constitution at dry dock in the Charlestown Navy Yard and wait for cannon fire to announce the setting of the sun.

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

Boston Harbor City Lights Boat Tour

City Lights Cruise

Unwind after a long day on land aboard a City Lights Cruise aboard motor yacht Northern Lights. Gaze at the glittering lights of the city as light dances on the waters of Boston Harbor. Sit back and relax with a loved one for a romantic after dinner cruise or see the City Lights with a group of friends to experience the twinkling lights of Downtown Boston.

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

Boston Jazz Cruise

Boston Jazz Cruise aboard Yacht Northern Lights

Grab that special guy or gal, or a couple of happy-footed friends who enjoy the sounds of live music and step aboard the elegant Northern Lights, for a journey back to the Jazz era. Allow your senses to take you back in time with the sights of our 1920s styled New England Yacht combined with sounds of jazz, presented by the Benjamin Young Trio. The Benjamin Young Trio is a young, talented, up-and-coming, group of Jazz musicians from the Berklee School of Music. Cruise through the harbor enjoying the City Lights as they dazzle on the waters of Boston Harbor, grab a glass of champagne or a mixed drink from the bar and dance with your sweetheart on this one of a kind cruise. This is the perfect cruise for snuggling up with a loved one’s or dancing with a group of friends to the sounds of the Benjamin Young Trio.

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

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

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

Irish Celtic Band on classic boat in boston

Boston Celtic Cruise

Take a cruise aboard the elegant Northern Lights, a 1920s New England Yacht, for a one of a kind experience, an Irish Band paired with a Harbor Cruise. While aboard enjoy Irish tunes inspired by historical events (i.e. the Great Molasses Flood of 1919, etc.), classic Boston Irish songs, authentic Irish tunes, and sea shanties. See the sites of some of these historical tunes while out on a Harbor Cruise. This event aims to be a culturally stimulating and historical informative experience through Boston Harbor. Learn about some of the history of Boston through song and perhaps a little dance, if you’re up to it.

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

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 Full Moon Cruise

Full Moon Cruise

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. Sit back and relax with a loved one for a romantic after dinner cruise or with a group of friends to see the full moon and city lights of Boston. Northern Lights offers a unique cruise to experience the twinkling lights of South Boston and Downtown Boston.

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

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

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

Boston Harbor Sunset Cruise with Classic Harbor Line

Band on the Water, Fire in the Sky aboard Northern Lights

The Boston Minstrels, featuring Tim McHale, take to the water to offer guests a fun new experience for a Sunset Cruise. As we cruise through the harbor enjoy live music through the ages in all types of genre such as: rock, pop, folk, and blues. You will surely know the songs and will easily embrace the sound waves as we cruise through the waves aboard Northern Lights. The microphone is yours, if you want it, and so is the dance floor. This is meant to be a fun-filled night on the water with friends and loved ones. Have a blast with us on this one of a kind cruise through Boston Harbor.

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

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