Classic Harbor Line cruises: Tour iconic Manhattan architecture aboard a luxury yacht

Seen from the window of a descending plane, or through the levitating bubble of a sightseeing helicopter, Manhattan's urban landscape resembles a silver forest of soaring skyscrapers, punctuated by the bright green blanket of Central Park. Seen from the water, the focus shifts to bridges, perimeter-skirting structures and that mesmerising skyline.

It comes as a surprise to learn Manhattan is a small island, a sliver of land surrounded by water. So huge does New York City's skyscraper-filled borough loom – culturally, cinematically, financially, architecturally – that it seems impossible she's not even a tenth the size of Tasmania.

Crammed within those 59 square kilometres are some of the most famous and easily recognised buildings in the world. From Beaux Arts beauties of the 19th century through to the futuristic works of today's "starchitects" including Renzo Piano, who designed the new Whitney Museum and Midtown's New York Times building, the city is a masterpiece of its own making. The Empire State Building, One World Observatory, the Chrysler Building, the gargantuan Hudson Yards project and so many more iconic landmarks on a grand scale define Manhattan. Such a grand scale, in fact, that a bit of distance is needed to take it all in.

The New York chapter of the American Institute of Architects figured there must be plenty of people who would like to learn about the city's built footprint from the comfort of a round-Manhattan cruise, especially if that cruise was enjoyed on board a 1920s-style yacht.

Teak-detailed and comfortably elegant, the vessels bring to mind a casual outing on Long Island with Jay Gatsby and co. Throw in a complimentary glass of champagne and some tasteful snacks, and it's as far away from a Statue of Liberty sightseeing booze cruise as you can get.

Now in its ninth season, the AIA cruise series is offered in association with Classic Harbor Line and departs from the fleet's marina at Chelsea Piers. Led by docents, authors and architecture experts, the tours feature running commentary – an impressive feat at almost three hours long.

The original Manhattan circumnavigation cruise, AIANY Around Manhattan Architecture Tour, is a 50-kilometre journey past more than 150 significant sites. As the yachts cruise along the Hudson, East and Harlem Rivers, guests follow along on a marked map. Even for those repeat visitors who feel they know Manhattan inside and out, the river vantage point brings fresh perspective. Gliding under some of New York City's 18 bridges and sailing by bustling waterfront parks including Governors Island, you can almost reach out and touch the passing scenery.