What residents know, but visitors often forget, is that New York’s Financial District hosts a wealth of ways to get out onto the frothy waters that surround the island of Manhattan. Downtown workers can leave the office, walk to the docks, trade the briefcase for a cocktail, and climb aboard.
Now, unless you own your own boat, nobody’s going to let you captain a ship without any help. (No matter how many Lasers or FJs you sailed at summer camp, these boats are $50,000+ pieces of delicate machinery.) Instead, each charter boat has at least one sailor aboard who will actually raise the mainsail, lower the boom, unfurl the spinnaker, and act out any other lingo you might have picked up from Captains Courageous. You and your friends get to sit back, enjoy the view, and do your best not to get any of the East River in your mouth.
Starting on the smaller side of the spectrum, you can charter a 34.5' boat from Gotham Sailing. It holds up to six passengers, with the standard, four-hour charter going for $399.
In the same price range, you can charter a Tayana 37 from Narwhal Yacht Charters. Their Tayana, a brand whose vintage-inspired wood and metal finishes (and ease of use) has earned a cult following, is available for four-hour cruises -- just contact the captain, Eric Puleio, for charter rates.
Atlantic Yachting, which sails from 79th Street boat basin, has two boats for charter -- a 43' and a 42' sloop. Each boat, staffed with two crew members, can hold a maximum of six passengers. The charter times vary from two to four-hour sails.
Now, before you rush out to the piers, it's important to remember that sailboats in this size-range will inevitably rise and fall with every wave; if you're hoping for a languorous cruise with martinis and board games, you should probably opt for something larger.
Which brings us to the Atlantic Sail and Charter, which mans a stunning, 62.5' long wooden sailboat from 1921, which holds up to 25 passengers. It's as classic as they come -- built for the founder of Citibank, it’s got a mahogany hull and enough teak to reforest Burma.
And then there’s the Classic Harbor Line, which offers a 105 foot, three-mast schooner that can hold up to 75 guests. Weekday evenings cost $1,375 per hour, with a two-hour minimum.
The beauty of all of these options is that they require minimal commitment: you're not joining a yacht club or buying a boat -- at most, you're taking a cab.