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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 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.

  Duration: 2.5hrs   Boat: Northern Lights   Cost: $70

Cinco De Mayo Cruise

Join us on the water this Cinco De Mayo for the best way to kick off the summer- cruising Boston Harbor. This cruise will feature a festively decorated boat, a fully stocked taco bar, with a specialty drink menu for sale, so you can get your tequila fix. This two-hour cruise will take place board luxury motor yacht Northern Lights. She features two decks, so we can go out rain our shine; the bottom deck is enclosed and climate controlled, while the top deck is open.

  Duration: 2 hrs   Boat: Northern Lights   Cost: Adult $55

Spring Luncheon Cruise

We’ve had enough of winter! So brush off the cobs webs on your spring attire it’s boating season again! Join us on a cruise through New England harbor and taken in the beautiful flora and fuana of spring on this 2-hour cruise. All spring long we are rewarded with blooming cherry blossoms, dogwoods, black cherry trees, and rhododendrons as we cruise around the harbor. Take in the pink and soft green colors of spring on the Boston Harbor Islands while hearing stories about pirates and ghosts that haunt the islands. Additionally, the islands have played an integral role in fortifying Boston in every war from the Revolutionary War until the World War II. Almost every island has a tale to tell. Aboard this cruise, you will hear many of those anecdotes. Gourmet picnic lunch consisting of an assortment of sandwiches, fruit, chips and desserts is included with your ticket. This cruise is excellent for families, friends exploring the town, and folks looking for a relaxing adventure.

  Duration: 2 hrs   Boat: Northern Lights   Cost: Adult $55

Drag Brunch Cruise

This Pride Weekend Classic Harbor Line Boston is so excited to celebrate with our LGBTQ community by hosting our first ever Drag Brunch Cruise! This 2.5-hour event will feature signature cocktails for purchase, includes a gourmet brunch menu, and Boston crowd favorites Sham Payne, Drag Queen JP, Missy Steak, and Magnum Sin. Select a cozy seat aboard Northern Lights, sit back and enjoy the show as we capture the perfect panoramic views of Boston harbor this Pride!

  Duration: 2.5 hrs   Boat: Northern Lights   Cost: $70

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.

  Duration: 2 hrs   Boat: Adirondack III   Cost: $45

Summer Luncheon Cruise

A 2-hour summer cruise through Boston harbor is an exceptional way to spend the day. Whether you’re entertaining clients on a long lunch, taking friends out to see the city the beauty of Boston Harbor, or taking the family on a educational cruise. The islands have played an integral role in fortifying Boston in every war from the Revolutionary War until the World War II. Almost every island has a tale to tell. Aboard this cruise, you will hear many anecdotes. While aboard enjoy a gourmet picnic lunch consisting of an assortment of sandwiches, fruit, chips and desserts is included with your ticket. This cruise is excellent for families, friends exploring the town, and folks looking for a relaxing adventure.

  Duration: 2 hrs   Boat: Northern Lights   Cost: Adult $55

Summer Barbecue & Beers Cruise

Hooray! Summer has arrived and there are two things we do in the summer time in Boston and that is boating and barbecues! Put them together on this 2-hour cruise through Boston harbor. We’ll pull out the corn hole and turn up the beach boys as we create a unique summer event for you. Bring a few friends and grab a few seasonal beers from the bar do summer like a pirate! While on this cruise we’ll point out some of our notable sites on the harbor islands that have played an integral role in fortifying Boston in every war from the Revolutionary War until the World War II. Almost every island has a tale to tell. Our gourmet barbecue cruise consists of delicious smoked chicken and honey glazed BBQ ribs, coleslaw, biscuits, and roasted potatoes is included with your ticket. This cruise is excellent for families, friends exploring the town, and folks looking for a different adventure.

  Duration: 2 hrs   Boat: Northern Lights   Cost: Adult $55

Boston Harbor Island Sightseeing Cruise

Historical New England Harbor 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.

  Duration: 2 hrs   Boat: Northern Lights   Cost: $40

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 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.)

  Duration: 2 hrs   Boat: Adirondack III   Cost: $125

Boston Holiday Brunch Cruise

Holiday Brunch Cruise

Take a relaxing morning cruise through the Boston Harbor on our Boston Holiday Brunch Cruise in the warm, cozy, and festively decorated interior of Northern Lights. While aboard, warm up with a cup of hot cocoa from our hot chocolate bar and enjoy the harbor sites with friends and family! 

  Duration: 2.5 hrs   Boat: Northern Lights   Cost: $70

New Year’s Day Brunch Cruise

Start your year off on the right foot and step aboard the luxury yacht Northern Lights for a New Year’s Day Brunch Cruise! Take a relaxing morning brunch cruise through Boston Harbor on this New Year’s day in the warm, cozy, and festively decorated interior of this stunning yacht. While aboard, warm up with a cup of hot cocoa from our hot chocolate bar and enjoy the harbor sites with friends, family or a loved one.

  Duration: 2.5 hrs   Boat: Northern Lights   Cost: Adult | $75

Boston Sightseeing Boat Tour on Yacht Northern Lights

Boston Harbor Fall Foliage Luncheon Cruise

Pull out your autumn sweaters and grab a hot cider and join the captain and crew of Northern Lights for a relaxing Boston Harbor Fall Foliage Cruise, featuring the colorful trees of fall. New England has been known for the vibrant foliage that people are drawn to every year. So grab your friends and family and enjoy some time out on the water for this Fall Foliage Cruise.  This time of year is a magical with the change of the season and New England does it best.  Let our professional crew cater to you as embark on this breathtaking boat adventure.  

  Duration: 2 hrs   Boat: Northern Lights   Cost: Adult $55 | Child $40

Boston Fall Foliage Brunch Cruise

Weekends are a time for relaxing and getting your days started the right way. Join us for a Mimosa and Bloody Mary Cruise aboard the elegant Northern Lights to jump start your relaxation mode. 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.

  Duration: 2.5 hrs   Boat: Northern Lights   Cost: Adult $70 | Child $44

Boston Fall Foliage Cruise

Northern Lights Fall Foliage Cruise

A Boston Fall Foliage Cruise is the perfect event to pull out that fall wardrobe.  Pull out your autumn sweaters and grab a hot cider and join the captain and crew of Northern Lights for a relaxing Boston Harbor cruise, featuring the colorful trees of fall. New England has been known for the vibrant foliage that people are drawn to every year. Our **three-hour extended afternoon picnic cruise** will take you away from the hustle and bustle of the city to the peaceful majesty of the harbor islands for this Boston Fall Foliage Cruise. Enjoy this magical cruise with us and capture the best photos of the Harbor. 

  Duration: 2 hrs   Boat: Northern Lights   Cost: $68