Sunset Evening Jazz Cruise in Boston

Classically Designed for a Contemporary Experience

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.

Our Crew

Classic Harbor Line is the operating company of schooner Adirondack III and luxury yacht Northern Lights of Rowes Wharf. Operating sightseeing trips in Boston Harbor waters since 2013, Classic Harbor Line specializes in bringing beautiful, classic-style vessels to Boston’s waterways and creating special and memorable excursions.

Our Crew, including all captains, mates, and on-land representatives at Classic Harbor Line, are what make the experience on our beautiful yachts truly magical. We have maintained a consistent history of not only operating with a professional staff, but also with warm and inviting hosts. You will, without a doubt, have fantastic views of the city and find the boats beautiful and comfortable. What will surprise you and stay with you when you leave is the warm and special treatment you receive from our extraordinary team.

Our Captains
All of our captains are Coast Guard certified. The schooner captains all have a minimum 50-ton license and a sailing endorsement. Northern Lights captains all have a minimum 100-ton license. Our captains are also trained in first aid and CPR and are registered in an ongoing drug-testing program. Perhaps of equal importance, we require that our captains have an appreciation for quality service and are extremely charming hosts.

Our Mates
Mates on both the motor yacht and the sailing ship undergo extensive safety and marine training. Many of the schooner mates also have extensive sailing, racing and/or teaching experience on smaller sail vessels.

Our mates are widely remembered for their remarkable hospitality and personality, which is consistently praised in our customer reviews. They love talking with our guests, sharing information on the great city of Boston, and conveying their love for our classic-style yacht.

Our Boats

The Schooner Adirondack III
Adirondack III was designed and constructed specifically for carrying passengers comfortably, which is uncommon for historic schooners. Due to the modern and innovative design of Adirondack III, guests will have room to sit and move around the boat. Adirondack III measures 80 feet in length overall with a 16-foot beam. Her lines are modeled after 1890s style pilot schooners. Adirondack III is long and lean with a spoon bow, which helps her ply through the waters more effortlessly than the average schooner. An all-wooden vessel with a white glass overlay haul, Adirondack III is quite easy to pick out amongst her fellow schooners with her smooth clean lines.

The Yacht Northern Lights
Take a cruise on Northern Lights, a Turn-of-the-Century inspired yacht that is available daily to take guests on cruises through Boston Harbor to see Boston’s iconic waterfront sites and monuments. Northern Lights measures 110-feet in length along her waterline and expands to a 28-foot beam. She was built with a beautiful mahogany bar, ceiling accents, ceiling trim, and railings.

Comfortable seating is available in the interior, first floor, climate-controlled cabin, while bench seating is provided on our open bow and covered top deck, which offers un-obscured views of Boston Harbor and the skyline!