Classic Harbor Line-Boston
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Dedicated to helping locals & visitors alike enjoy the unique wonders of Boston, Classic Harbor Line
Classic Harbor Line: Boston’s Classic Style Charter Boat and Tour Boat Fleet
At Classic Harbor Line, we are dedicated to providing the most impeccably luxurious and hospitable sailing experience in Boston. Our guests can look forward to the privilege of being escorted on a breathtaking excursion aboard the most elegant sailing vessel in Boston Harbor, the schooner Adirondack III or a relaxing cruise aboard the motor vessel Northern Lights If you are a first time visitor or a seasoned local, an excursion aboard one of Classic Harbor Line’s yachts will provide you with a new perspective on the city of Boston. While aboard our stylish boats, you will be treated to views of the spectacular Boston skyline, historical sites, harbor islands, and perhaps a glimpse of some of our elusive wildlife, such as the harbor seal. So, come on out and experience the best sightseeing adventure in Boston! And please, kick up your feet because we’ll do all the heavy lifting (and drink pouring)! There are two ways to cruise or sail with us, you may purchase tickets for one of our public events aboard the schooner Adirondack III or motor yacht Northern Lights or you may privately charter either boat. Tickets aboard our schooner are available for purchase on a Day Sail, Sunset Sail, City Lights Sails, Boston Harbor Island Picnic Sail, or our Sails & Ales featuring Harpoon Brewery. Northern Lights offers tickets on our One-Hour Inner Harbor Cruise and Sunset Cruise. Consider the schooner Adirondack III or yacht Northern Lights if you are looking for a new and exciting experience to host your next company outing or celebrate a milestone such as a wedding, anniversary, or birthday. Adirondack III is certified to carry groups of 40 or less, while the yacht Northern Lights is suitable for groups of 149 or fewer. To get more information on privately chartering the schooner Adirondack III or Northern Lights for your next event, go to our Private Charters page. Either way, you choose to experience Boston Harbor with us you will be pleased to find our vessels in excellent condition, with comfortable seating, and the most hospitable crew in Beantown. Classic Harbor Line is known for operating some of the most stunning sailing boats and classic yachts in New York, New York; Newport, Rhode Island; Key West, Florida; and Boston, Massachusetts. In addition to our beautiful vessel, we are also renowned for our excellence in hospitality and customer service.
10/04/2026
"Took an awesome sailboat cruise of Boston Harbor with the crew of the Adirondack II. It was a wonderful experience, highly recommend." says Bill on Google
Classic Harbor Line Boston | Boston, MA ★★★★★ Took an awesome sailboat cruise of Boston Harbor with the crew of the Adirondack II. It was a wonderful experience, highly recommend.
10/02/2026
"The day sail was awesome! Kira and Alex were so nice and really knew what they were doing. The service was quick and exceptional. I would definitely come back on this boat! They made the ride fun :)" says Kadine
Kadine P.'s review of Classic Harbor Line Boston The day sail was awesome! Kira and Alex were so nice and really knew what they were doing. The…
10/02/2026
"An absolute gem of an experience. Kira, Alex, and Mike are fantastic sailors and super knowledgable of Boston. So glad I got to come out! Thank you!" says Zoe on Google
Classic Harbor Line Boston | Boston, MA ★★★★★ An absolute gem of an experience. Kira, Alex, and Mike are fantastic sailors and super knowledgable of Boston. So glad I got to come out! Thank you!
09/28/2026
"My husband booked us a sunset sailboat tour and it was beautiful! We were offered drinks during the trip. We were lucky and got a beautiful view that night! But it definitely was cold out there, so I would plan accordingly for your dress attire, depending on the tour you pick, the time of day and the season." says Megan on Google
Classic Harbor Line Boston | Boston, MA ★★★★★ My husband booked us a sunset sailboat tour and it was beautiful! We were offered drinks during the trip. We were lucky and got a beautiful view that night! But it definitely was cold out there, so I would plan accordingly for your dress attire, depending on the tour you pick, the ti...
09/25/2026
"The sunset cruise on Adirondack should be on everyone’s to-do list! Captain Kachel, Kira and Zoe were amazing and the views from the water were beautiful Such a fun way to spend a couple hours in Boston. Perfect for families, work outing, date night or girls night out. Will definitely go again!" says Kathleen on Google
Classic Harbor Line Boston | Boston, MA ★★★★★ The sunset cruise on Adirondack should be on everyone’s to-do list! Captain Kachel, Kira and Zoe were amazing and the views from the water were beautiful Such a fun way to spend a couple hours in Boston. Perfect for families, work outing, date night or girls night out. Will definit...
09/20/2026
"Amazing views, loved how the captain was talking to us about some history. Great conversation and great company!" says Cindy
Cindy C.'s review of Classic Harbor Line Boston Amazing views, loved how the captain was talking to us about some history. Great conversation and…
09/19/2026
"What a great experience, we will be back!!! Charlie, Vitya and Mike were amazing hosts!!" says Adam on Google
Classic Harbor Line Boston | Boston, MA ★★★★★ What a great experience, we will be back!!! Charlie, Vitya and Mike were amazing hosts!!
09/13/2026
"Can’t recommend Classic Harbor Line and the 2-hour Adirondack II day sail enough — especially on a gorgeous afternoon! As Boston locals who had never been on a sailboat, we spontaneously booked tickets when the weather hit the low 70s and sunny.
Their fleet is incredible and the staff is exceptionally warm, knowledgeable, and skilled, and having drink options throughout the trip made it even better. One of the crew.." says Karly on Google
Classic Harbor Line Boston | Boston, MA ★★★★★ Can’t recommend Classic Harbor Line and the 2-hour Adirondack II day sail enough — especially on a gorgeous afternoon! As Boston locals who had never been on a sailboat, we spontaneously booked tickets when the weather hit the low 70s and sunny. Their fleet is incredible and the ...
It may be rainy today but it will be sunny tomorrow!
Are you sailing or cruising with us this week? Let us know in the comments! ⬇️
09/13/2026
"It was fun and enjoyable the crew was great. It was a very windy day. It was our very first time going on a sail boat. And it will not be our last. Again great experience. The crew was Michael, Alex and we didn't travel the third name but, it was 2 guys and a girl." says Barbara
Barbara G.'s review of Classic Harbor Line Boston It was fun and enjoyable the crew was great. It was a very windy day. It was our very first time…
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Address
70 Rowes Wharf
Boston, MA
02110
Opening Hours
| Monday | 10am - 9pm |
| Tuesday | 10am - 9pm |
| Wednesday | 10am - 9pm |
| Thursday | 10am - 9pm |
| Friday | 10am - 9pm |
| Saturday | 10am - 9pm |
| Sunday | 10am - 9pm |
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