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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, you are surely to enjoy. 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 up 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 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: 1.5 hrs OR 2 hrs   Boat: Adirondack III   Cost: Adult $45 for 1.5 hrs | Adult $48 for 2 hrs

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

Boston Harbor Sightseeing Cruise

Boston Harbor Cruise on Northern Lights

Step aboard Northern Lights for a 1.5-hour sightseeing cruise of Boston Harbor.  The harbor is full of rich and unique history that will keep your attention throughout the trip. Grab a hot beverage or small bite from the bar.   Sit back, and relax aboard the warm and cozy Northern Lights!

  Duration: 1.5 hrs   Boat: Northern Lights   Cost: Adult $30 | Child $18

Summer Barbecue & Beers Cruise (Series)

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 1.5-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 and do summer like a pirate! This year were bringing a new and exciting spin on our Summer BBQ Cruises and offering a series of different menus. Check out the below date ranges
 
Series Menu Rotation
May 25, 2019 – June 16, 2019 (not available on June 9): Texas style BBQ, Austin, Cornbread
June 17, 2019 – July 7, 2019: Argentinian style gaucho BBQ, Beef, Chimichurri, etc.
July 8, 2019 – July 28, 2019: North Carolina style BBQ, Vinegar mustard BBQ Sauce
July 29, 2019 – August 18, 2019: Jamaican Jerk BBQ, Greens, Allspice heavy
August 19, 2019 – Sept 8, 2019: Spanish Seafood BBQ, Paella, Peppers
September 9, 2019 – September 28, 2019: Hawaiian BBQ, Roast Pork, Rice, Pineapple BBQ Sauce
 
**Other items are included in the menu but are not listed. List is meant to describe a brief description of the series**
  Duration: 2 hrs   Boat: Northern Lights   Cost: Adult $57

Boston Tea Party Cruise

Spend the afternoon with us for a Boston Tea Party Cruise. Step aboard Northern Lights for a tasty lunch with tea inspired cocktails! Enjoy the outdoors from inside a warm and cozy solarium aboard Northern Lights. Have fun playing classic yard games inside our main cabin, amidst tropical plants scattered throughout the salon to help rid you of the winter blues and make you feel like spring is near! While cruising the harbor enjoy our light narration and a delicious cocktail to warm the soul.

  Duration: 1.5 hrs   Boat: Northern Lights   Cost: Adult $40 | Child $30

U.S.S. Constitution Turnaround Brunch on Northern Lights

Join us for the July 4th turnaround cruise of the U.S.S. Constitution, the oldest (1797) actively commissioned naval vessel in the world . You won’t want to miss this truly unique and special event! The turnaround takes place once a year to celebrate our nation’s birthday. During the turnaround cruise the U.S.S. Constitution will sail out into Boston Harbor where she’ll exchange a 21-gun salute with Castle Island’s Fort Independence. After he salute, she will head back into the inner harbor and exchange cannon fire with the sector Boston’s United States Coast Guard base located in the North End. During our excursion please enjoy a three course brunch made fresh aboard the vessel. 

  Duration: 3 hrs   Boat: Northern Lights   Cost: Adult $130

Boston USS Constitution Turnaround Sail

U.S.S. Constitution Turnaround Sail aboard Schooner Adirondack III

Join us for the 2.5-3 hour long sail on July 4th to view the turnaround of the U.S.S. Constitution, the oldest (1797) actively commissioned naval vessel in the world. Experience this yearly event like you never have before aboard Adirondack III, a classic 80-foot pilot schooner. She features comfortable seating and a brisk ride, as we are able to view the turnaround of the U.S.S. Constitution. You won’t want to miss this truly unique and special event! The turnaround takes place once a year to celebrate our nation’s birthday. The U.S.S. Constitution will sail out into Boston Harbor where she’ll exchange a 21-gun salute with Castle Island’s Fort Independence. While aboard enjoy complimentary pastries, bagels, and muffins with our continental breakfast.  (Continental breakfast includes: Assorted Pastries, Scones, and Muffins, Jalapeño Cheese Bagels with Cream Cheese, Fresh Seasonal Fruit, Yogurt and Granola)

  Duration: 2.5 - 3 hrs   Boat: Adirondack III   Cost: Adults $130

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 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 $57 | Child $45

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

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

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 hrs   Boat: Northern Lights   Cost: Adult $75 | Child $50

Boston Sightseeing Cruise

1-hr Boston Harbor Cruise

Take a cruise on the elegant Northern Lights for a glimpse into the glamour of the Roaring 1920s. Relax with the sea breeze on one of our top deck benches or chill inside with our climate controlled, wood trimmed salon. Throughout the cruise, our local captains will share their knowledge and personal stories of growing up in Boston Harbor. Crew will be around to assist pointing out sites and making sure you feel comfortable and cozy on our relaxing and elegant cruise in the harbor.

  Duration: 1 hr   Boat: Northern Lights   Cost: Adult $22 | Child $12

Boston Brunch Cruise

Galentine’s Day Brunch Cruise aboard Northern Lights

Valentine’s Day always reminds to spend and shower our closest companion with love, but let’s not forget about the people that always have our backs! That’s right, your BFF from way back when you had braces, owned a crimper, and wore way too much aqua net! Let’s not forget the love of friendship this year and treat your favorite ride or die gals to a fabulous, boozy, and relaxing brunch cruise aboard Northern Lights! Wanting to make it just a touch more special, ask a crew member to make an announcement and toast your Galentines! Let us know how long you’ve been building your amazing friendship!
  Duration: 2 hrs   Boat: Northern Lights   Cost: $70

Boston Harbor Sightseeing Cruise

Winter Harbor Cruise on Northern Lights

Step aboard Northern Lights for a 1.5-hour sightseeing cruise of Boston Harbor. The harbor is full of rich and unique history that will keep your attention throughout the trip. Grab a hot beverage or small bite such as a Cup of New England Clam chowder from the bar. It’s a staple here in Boston, and you can’t have a New England experience without it. Cape Cod author, Joseph C. Lincoln describes clam chowder as,“… a dish to preach about, to chant praises and sing hymns and burn incense before. To fight for. The Battle of Bunker Hill was fought for—or on—clam chowder; part of it at least, I am sure it was. It is as American as the Stars and Stripes, as patriotic as the national Anthem. It is ‘Yankee Doodle in a kettle.'” Sit back, and relax aboard the warm and cozy Northern Lights!

  Duration: 1.5 hrs   Boat: Northern Lights   Cost: Adult $30

Boston Pride Day Sail

Adirondack III Pride Day Sail

Our classic 2-hour or 1.5 hour 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 speediness to boot. This sail is great for families who want to get out and see the sights. 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!
  Duration: hoose a 1.5hr or 2hr sailing option   Boat: Schooner Adirondack III   Cost: Adults $48 or $45

Drag Brunch Cruise: Boston Pride

CHL Boston is happy to continue to support Boston Pride this year! A portion of each ticket on the Pride Drag Brunch Cruise will be donated to BAGLY, The Boston Alliance of LGBTQ+ Youth, a youth-led, adult-supported organization committed to social justice, and creating, sustaining and advocating for programs, policies and services for the LGBTQ+ youth community. Whether you are part of the community or not, if you want to support- all allies are welcome on the Drag Brunch Cruise! Featuring Boston crowd favorites, Drag Queen JP, Sham Payne, Plane Jane, and Veronica Vandersnatch, this pride your beloved hosts Secret Queen and Kirbie Fully Loaded will bring you a show you won’t soon forget. This 2.5-hour cruise aboard yacht Northern Lights includes a three-course brunch menu and will feature local DJ Discodungeon spinning all your favorite summer jams. So grab one of our signature cocktails and get your dollars ready Boston, because the Pride Drag Brunch Cruise is back and better than ever!
  Duration: 2.5 hrs   Boat: Yacht Northern Lights   Cost: Adult $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 2.5-hour event with including 2-hour cruise, will take place board luxury motor yacht Northern Lights. She features two decks, so we can go out rain or shine; the bottom deck is enclosed and climate controlled, while the top deck is open. 

  Duration: 2.5 hrs (30-minutes dockside, 2 hr cruise)   Boat: Northern Lights   Cost: Adult $55