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 hull, Adirondack III is quite easy to pick out amongst her fellow schooners with her smooth clean lines.

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Scarano Boat Builder

Boat Builder


Scarano Boat Builders designs and builds period wood, aluminum, composite and steel boats, Coast Guard certified for public transportation and excursions. Scarano Boat has developed a national reputation for modern wood construction and is the builder of all of Classic Harbor Line’s vessels. They are a related company and shared ownership.

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Yacht Manhattan

Yacht Manhattan (ONLY available for the month of December)


This gorgeous, buff-hulled 80-foot, Twenties-style yacht offers elegance and comfort, wrapped in turn-of-the-century tradition. She is equipped with teak decks and mahogany trim. Her spectacular cabin features an all-glass observatory, cushioned seating, conversation-friendly tables, and a well appointed bar; all of which provide you and your guests with stunning panoramic views within climate-controlled comfort.

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Boston Private Boat Rental

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!

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Our Boats in Other Locations

Sloop Eleanor Newport RI

Sloop Eleanor


Meet the newest member of our fleet, Eleanor. Just launched in Albany in May 2016, she’s a custom designed Scarano 48’ sloop that can accommodate up to 24 guests in her roomy cockpit with wrap around seating. Her size and classic lines make Eleanor the perfect boat for more intimate corporate and private sailing charters, leisurely day sails and sunset cruises on Newport Harbor and Narragansett Bay. Sit back, relax and enjoy the beautiful coastal scenery while our experienced captain and knowledgeable crew fill you with the lore of yesteryear while sailing on the bay. She becomes available for ticketed sails approximately a week before the date.

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The Yacht Manhattan II


This epic, white-hulled 100-foot long & 22-foot beam yacht echoes everything that the first Yacht Manhattan is, but with more space, more glass and more accommodations. Manhattan II’s 1920s-inspired design continues with her hull shape and fine features, including teak decks and mahogany finishes.

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Schooner Adirondack

The Schooner Adirondack


This elegant, 80-foot, 1890s-style pilot schooner is a gem in New York Harbor. Schooner Adirondack has been sailing in the New York City Harbor since the fall of 1999. She has entertained thousands of NYC visitors and locals, and has attracted a large, and growing, number of passionate regulars who can’t stop coming back for more.

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Schooner America 2.0

The Schooner America 2.0


Offering our most premium sailing experience, Schooner America 2.0 is the newest, largest, most elegant vessel designed for Classic Harbor Line. Added to the Classic Harbor Line fleet in 2011, America 2.0 offers the most exceptional day sailing one can find. She is the fastest, most refined, and the most comfortable schooner of the fleet.

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Oct-May in Key West 

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May-Oct in NYC  

Yacht Kingston

The Yacht Kingston


This white-hulled, fan-tailed, plumb-bowed mini-yacht is a real charm in the Classic Harbor Line fleet. Certified for up to 49 guests, we are accustomed to hosting no more than 32 or her special, intimate tours and excursions.

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Schooner Adirondack II

The Schooner Adirondack II


Adirondack II has all the elements of a turn of the century pilot schooner and would have looked right at home in Narragansett Bay 100 years ago. The rig on Adirondack II is held in place with Kevlar shrouds, and her underbody carries external ballast taking advantage of modern wooden boat building techniques. The modern underbody is certainly designed in the spirit of the original pilot schooners, which used all the technology available to them to make their vessels as fast and yet as safe as possible. These modern design techniques help to provide a more exciting sailing experience. This elegant, 80-foot, turn-of-the-century-style pilot schooner has been a local mainstay in Newport since it joined the Scarano boat fleet in 1999.

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in Newport, RI  

Yacht Full Moon with the NYC skyline in the background

The Yacht Full Moon


The Yacht Full Moon is a Grebe Yacht: What is a Grebe Yacht? Henry C. Grebe & Company was the successor to Great Lakes Boat Building, which had started in Milwaukee in 1915 and moved to Chicago in 1921. Grebe was famous for the style and quality of the leisure yachts he designed and built. It was located on the west side of the North Branch of the Chicago River, just north of the West Belmont Avenue Bridge.

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