Cruising the waterways of harbor, port, river, and coastal cities by boat is a time-honored tradition around the globe. My past excursions include Atlantic City, Chicago, Fort Lauderdale, Providence, and Miami, with international outings in Stockholm, Sydney, Vancouver, and the mother of all water cities, Venice.
Educational, eye-opening, and enrapturing, each perspective-changing experience deepened my appreciation of the given locale’s maritime, architectural, ecological, and other attributes.
With 520 miles of waterfront—more than Miami, Boston, Los Angeles, and San Francisco combined—my hometown of New York City ranks among the world’s greatest urban archipelagos. Manhattan anchors a chain of up to 40 local islands that include iconic immigration gateway Ellis Island and Liberty Island, home of the Statue of Liberty.
Emerged in the immense Hudson-Raritan Estuary, NYC’s vast waterway network, including the Hudson and East Rivers, is a cruising wonderland. According to Circle Line Sightseeing Cruises, which celebrates 80 years of service in 2025, NYC boat tours date to the 1890’s. In 1908, a steamer, aptly named Tourist, inaugurated the first regular sightseeing cruise around Manhattan.
America 2.0 Sailing In Key West (Photo by Classic Harbor Line)
Three years ago, I was introduced to Classic Harbor Line (Tel. 212-627-1825. sail-nyc.com), an exceptional NYC-based East Coast operator that became an instant favorite. Offering a range of ticketed, chartered, and specialty seasonal and year-round sightseeing, leisure, educational. and other programs in NYC, Newport, Boston, and Key West, this classy enterprise stands out with its fleet of elegant period vessels that combine Old World charm with advanced modern technology.
The company originated with Albany, NY based Scarano Boat Building Inc. (scaranoboat.com), a family business launched in 1974 by President and Lead Designer John Scarano. As kids, Scarano and his brother Rick, also with the company, learned to sail on an Upstate New York lake in a rigged-up “tub” they had fashioned from cutting a World War II bomber fuel tank in half.
Their passion and ingenuity became the foundation for their nationally-renowned namesake company, which builds a wide range of custom and commercial vessels in their boat yard in the Port of Albany. Specialties include certified historic replica passenger vessels with classic stylings and appointments from yachting’s glory days in the mid-19th to early 20th century.
Adirondack III Flies Pride Flag For New York Harbor PRIDE Sail Fundraiser For HMI (Photo by Classic Harbor Line)
In 1994, the Scaranos built one such boat, the 80-foot schooner Adirondack, for Sailing Excursions Inc., their co-owned day sailing operation in Newport. Five years later, they founded Chelsea Excursions, LLC to operate a second schooner, the Adirondack II, in New York Harbor. Each better suited for the other locale, the boats were swapped and the Adirondack commenced full operations in NYC in 2000. Adding the motor yacht Manhattan in 2005, with an official christening by legendary late broadcast journalist Walter Cronkite, the Scaranos renamed the company Classic Harbor Line (CHL). After expanding to Key West in 2008 and Boston in 2013, CHL’s fleet today comprises 14 Scarano-built or acquired period-style boats across all four locations.
To date, I have been on three CHL excursions around NYC’s waterways. All departing from Pier 62 at the northern end of historic Chelsea Piers on the Hudson River where the Titanic was bound on her ill fated maiden voyage in 1912.
Manhattan II Cruising The Hudson River Along The Palisades (Photo by Classic Harbor Line)
My first CHL cruise, in May 2022, was the “Around Manhattan Architecture Tour” aboard the 130-capacity Manhattan II motor yacht. One of five distinct CHL programs offered daily in partnership with the New York chapter of the AIA (American Institute of Architects) since 2009, our three-hour circumnavigation, narrated by a lively AIA New York expert, revealed Manhattan’s beguiling architectural, engineering, and maritime history. We also learned about ongoing planning, conservation, and other initiatives impacting NYC’s once dilapidated, now flourishing waterfronts, such as the development of public parks and the Billion Oyster Project.
Like her sister, Manhattan II follows a 1920s inspired design, including a white hull, teak decks, and mahogany finishes. The climate-con trolled main cabin features an all-glass observatory, assigned tables with cushioned seating, and well-appointed bar. Tickets include a complimentary drink and sandwich, with beverages and light fare available for purchase.
Welcoming, personable, and professional, the captain and crew were consummate hosts. Passengers are free to roam the outer decks, where an external PA system broadcasts the narration and stories of so many beloved buildings, bridges, and landmarks. This wonderful experience had me falling in love with the city all over again after four decades of living here.
In June 2024, I set sail just before sunset aboard the Manhattan 1 for the three-hour “Urban Naturalist Tour” of the abandoned islands populating the East River. Renowned urban naturalist Gabriel Willow told transporting tales of one rocky outcropping after another, from Roosevelt Island, with its multiple former names and past incarnations, including hog farm, penitentiary, asylum, workhouse, and smallpox hospital, to the notorious prison isle of Rikers Island.
Sailing past the whirlpooling waters of Hell Gate and its shipwreck graveyard below, we reached the North and South Brother Islands. Typhoid Mary was twice quarantined in the former’s now-ruined hospital. Jacob Ruppert, owner of the New York Yankees from 1915 to 1939, had a summer home on the former, where Babe Ruth once practiced his swing. Today, the sibling islands serve as seabird sanctuaries. As an avid birder, I was thrilled to see nesting and swirling black crowned night herons, snowy and great egrets, double-crested cormorants, and other local species. The full-blooded sunset and nightscape on our return reinforced NYC’s cinematic glory.
My most recent CHL adventure, in December 2024, was back aboard Manhattan II for CHL’s inaugural Willow-led Seals, Seabirds and Winter Wildlife Tour of Lower New York Bay. Lapping the shores of Brooklyn and Staten Island, these fathoms-deep waters are rich with marine life, including humpback whales.
Added to CHL’s expanding eco-focused Urban Naturalist series, our journey began with passage through Buttermilk Channel, the tidal strait between Brooklyn and reborn, multi-use Governors Island which dairy farmers once boated across to sell their milk in Manhattan markets. After sailing under the Verrazzano-Narrows Bridge, the longest suspension span in the Western Hemisphere, we circled the man-made Hoffman and Swinburne Islands. Constructed in 1860 from harbor dredging’s, the neighboring isles long served as quarantine centers for immigrants arriving with infectious diseases.
Newport Sailing (Photo by Classic Harbor Line)
In 1972, after serving as military hospitals during WW1 and later uses, the islands reverted to federal control as sanctuaries for nesting shore birds. Hunted almost out of existence a century earlier, wintering harbor seals returned over a decade ago to claim the isles as a stopover resting place. Basking on the rocks and frolicking in the water, these playful mariners put on a show along with the seabirds swirling around the guano-covered hospital ruins. In 1965, 11 “Greenwich Village-type beatniks” were arrested for making a nudie film on Hoffman Island. Treatments for cholera and yellow fever cases on Swinburne Island included champagne mixed with turpentine and being wheeled out in the cold. The dead were cremated on site. On a brighter note, Willow informed that NYC and the U.S. are global leaders in environmental and ecological protection legislation. A slow pass by Ellis Island and Lady Liberty brought us home.
Classic Harbor Line’s curated programs embody the quintessence of travel at its best: informative, inspiring, uplifting, exciting, transformative. Other NYC adventures beckon and I would love to sail with CHL in Newport (sail-newport.com/), Boston (boston-sailing.com/), and Key West (sail-keywest.com/). This is a company of passion and purpose with a caring heart that includes philanthropic support for organizations including the Hetrick-Martin Institute (HMI).
Founded in 1979, HMI is the nation’s oldest LGBTQIA+ youth organization serving queer and trans youth, primarily of color, between the ages of 13 and 24. Each June, CHL flies a nearly 400-square-foot Pride Flag from the mainsail of the Adirondack III for the New York Harbor PRIDE Sail fundraiser, with all proceeds donated to HMI.
