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Boston, MA

Sunset Sails/Cruises

Browse By Sunset Sails and CruisesJoin us for one of the most romantic things to do in Boston, or the best way to unwind after work:  A Boston Sunset Cruise, or Boston Sunset Sail! These Boston sunset boat rides are sure to give your date night a unique and nautical spark or allow you to destress from your long day at work with some friends. Cruise on a sailboat or luxury yacht through Boston Harbor to end your day or start your evening.  Set sail aboard one of our classic boats for an experience you are sure to never forget!  Sail through Boston Harbor and glide past the U.S.S. Constitution as the sun dips beyond the outline of Boston’s skyline. Take in the rich colors of the sky with a glass of Champagne in hand and the breeze in your hair. Allow us to help you sit back and relax and enjoy the most perfect Boston sunset cruise.

Whether you are on our sailing boat, or our motor yacht, our exceptional crew is sure to treat you with the most professional hospitality that will have you feeling that our yacht is your yacht. Cruise Boston aboard one of our classic boats for a peaceful and picturesque sunset. Whether you are sightseeing or wanting to take in the views, it is the perfect way to end your day.


Holiday Sunset Cruise

Step aboard the luxury yacht Northern Lights decked out in Holiday decor for a Boston Harbor Holiday Sunset Cruise.  Our captain will provide light commentary of Boston Harbors sightseeing highlights. And enjoy light Holiday music as it will be played throughout the trip. Watch the sky as it changes from blues to oranges behind the outline of Boston’s city skyline.

  Duration: 1.5 hrs   Boat: Northern Lights   Cost: $40

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.

  Duration: 1.5 hrs   Boat: Northern Lights   Cost: $38

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.

  Duration: 2.5 hrs   Boat: Northern Lights   Cost: Adult $68

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.

  Duration: 2 hrs   Boat: Adirondack III   Cost: $55 - $57

Boston Sunday Evening Jazz Cruise

Sunday Evening Jazz Cruise

Not ready to start the work week? We understand, take a relaxing Boston Sunday Evening Jazz Cruise aboard the luxury yacht, Northern Lights. Come with friends who enjoy the sound of live music and allow yourselves to unwind and forget about Monday for a little while longer. Join us for a sunset cruise around Boston Harbor with our live jazz band, 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 colors of the sky as it changes from oranges, to deep pinks and purples. Snuggle up with a special someone, on one of our cozy benches with a glass of champagne or a mixed drink from the bar and relax.

  Duration: 1.5 hrs   Boat: Northern Lights   Cost: $44

Boston Jazz Cruise

Boston Jazz Cruise aboard Yacht Northern Lights

What better way to enjoy and evening than on a Boston Jazz Cruise.  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 Boston Jazz Cruise for snuggling up with a loved one’s or dancing with a group of friends to the sounds of the Benjamin Young Trio.

  Duration: 1.5 hrs   Boat: Northern Lights   Cost: $44