I tested it for you… a sailing cruise in New York

I’ve spent plenty of time exploring New York Harbor by boat, but I have to admit I was genuinely curious as I boarded this sailing cruise. Unlike anything I’d done before, I’d never sailed across the bay in a proper schooner. I couldn’t wait to see what it would be like.
We met at 4 pm in Battery Park, between the Staten Island Ferry terminal and the Statue of Liberty departures, for a 1.5-hour cruise aboard the Clipper City. The beautiful wooden schooner caught everyone’s eye immediately. Boarding took just a few minutes, and finding a spot was easy—either up near Captain Chris or out on the main deck.
I settled in next to Captain Chris, a colorful character who reminded me of Captain Haddock: easygoing, with that salty sailor charm. Smiling and relaxed, this old sea dog put his passengers at ease right away with jokes and answers to every question.

All hands on deck

The lines were cast off, Captain Chris throttled up, and the ship headed slowly toward the East River, trailing smoke, while curious tourists watched from the shore. The captain launched into a brief history of his boat, bought on eBay years ago and completely restored. As everyone snapped photos of the Brooklyn Bridge and the Financial District, a passenger asked nervously: “Are you going to use the sails?” Captain Chris smiled, eyes twinkling, and shot back: “Of course—just wait.” He knew how to build suspense.
As the schooner turned toward the Statue of Liberty, the moment we’d been waiting for finally arrived. All hands on deck—Captain Chris surveyed his passengers and picked two of them to help his crew hoist the sails. The operation took only a few minutes, but it took real effort hauling on those lines. Then the captain cut the engines. Now the schooner moved only by the wind, sails fully deployed. “It looks like the ships in pirate movies,” one passenger marveled. “Those movies look like us,” Captain Chris grinned, proud of his vessel.
The Clipper City tacked gently and drew closer to the Statue of Liberty. The view was spectacular—Manhattan’s skyline on one side and the Verrazano-Narrows Bridge on the horizon.

Back to the age of sail

A few more photos, and the ship headed back toward Battery Park. The deck was peaceful and quiet. Then it was time to bring down the sails and return to the dock.
A sailing cruise is truly a wonderful way to experience New York Harbor—completely different from other tours. The Clipper City gives you the delightful feeling of stepping back several centuries, to the age of sail. Navigating by wind alone, with nothing but the sound of the breeze, is a remarkable experience.
For photographers, the masts and sails are obviously photogenic. Below you’ll find some of the photos I took aboard. I’ve also put together a video of the cruise, with “Sail Away” as the soundtrack.
For more information, visit the sailing cruise page.

The cruise in video

The cruise in photos