Pirate Sail takes the Hudson

Pirate Sail takes the Hudson | 12° West

Pirate Sail takes the Hudson

With rousing shouts of “Arrrrrggghh!” and “Avast!” a group of pirates stormed the Hudson River in New York City last Saturday. It was all in fun, of course. But unknowing passers-by surely did a double take to see sailors dressed in full pirate garb, and sailing boats transformed into pirate ships!

Pirate Sail takes the Hudson | 12° West

The pirate fleet sailing in front of Ellis Island. Photo: Todd Neville

What was the occasion? The annual Pirate Sail, a communal celebration of sailing and pirate fun organized by the Honey Badger Yacht Club. HBYC is a self-described collective of pirates and scalawags who sail the globe in search of adventure, merriment, and boat drinks. HBYC leader Captain John Hornswoggle McDuber originated the Pirate Sail in 2012. Since then, it’s grown into an annual event beloved by sailors from all around New York Harbor.

Pirate Sail takes the Hudson | 12° West

The Manhattan Yacht Club contingent for the annual Pirate Sail. Photo: 12° West

Pirates take the Hudson

Somewhere around noon (pirates aren’t known for their timeliness) all boats met near the Statue of Liberty, and the Pirate Sail commenced. Then the fleet proceeded to sail around New York Harbor. Water cannon battles ensued, and screams of laughter echoed across the water as boats jockeyed for position to attack their foes with streams of Hudson River water.

Pirate Sail takes the Hudson | 12° West

S/V Gitana, the flagship of the pirate fleet. Photo: Nitzan Levy

The pirate fleet was led by the HBYC flagship S/V Gitana. Gitana is a 1936 John Alden-designed wooden yawl – which is, let’s face it, the perfect pirate boat. Gitana’s teak decks and vintage ship’s wheel evoke a time when pirates ruled the high seas. The largest boat in the fleet (at almost 70 feet!) was the beautiful S/V Arcadia, designed by McCurdy and Rhodes and hailing from Oyster Bay, NY. The rest of the fleet included J/24s, Colgate 26s, J/105s, catamarans, and other private boats.

Pirate Sail takes the Hudson | 12° West

A pirate in boat shoes! Photo: 12° West

The well-dressed pirate

The beauty of the Pirate Sail is that it’s open to everyone. The only requirement is to be dressed like a pirate. To some that meant a bandana and an eye patch, while others demonstrated a real commitment to the theme with full-on pirate garb. Velvet frock coats, tri-cornered hats, breeches and puffy shirts were on glorious display.

Pirate Sail takes the Hudson | 12° West

Best-dressed pirate Cap’n Buttons. Photo: Anastacia Stathakis Duber

Turns out that actual pirates were often not so well dressed; their clothes were usually stolen (natch). So it wasn’t unusual to see a pirate in ill-fitting, mismatched garb plundered from some hapless seaman. The pirate captain, however, almost always dressed in fine style, wearing a velvet or brocade waistcoat, silk shirt, and exotic feathers in his leather hat. Apparently socioeconomic divisions existed even among the pirate class.

Hands across the harbor

For the Pirate Sail, all sailing clubs and private boats in New York Harbor are invited to join in the event. This year boats participated from Sailors NYC, Manhattan Yacht Club, and North Cove Sailing as well as other clubs in the area. The Pirate Sail is one of the only events in the area that encourages cross-club engagement. By promoting recreational sailing in the harbor, that’s a good thing for everyone.

After the sail, multiple events provided a place for pirates to compare sea stories. Sailors NYC hosted a barbecue at their dock in Jersey City, and S/V Arcadia welcomed pirates to their vessel docked at North Cove Marina in lower Manhattan. The crews celebrated the day’s plunder with tasty treats and pirate grog (aka rum). Prizes were awarded for the best pirate ship decorations and best male and female pirate costumes. We hear tell that some sailors may have continued on to Pier A for the after-after-party, in true pirate fashion!

Pirate Sail takes the Hudson | 12° West

The intrepid organizers of the Pirate Sail and after-party. Photo: Bob Finkelstein

So you might ask: what makes normally reasonable, grown adults dress in pirate costume and sail around ambushing each other with water cannons? The short answer is: it’s ridiculous, and ridiculously fun.

We live in such a chaotic world these days. The day-to-day news can be relentless and unsettling. Some good-natured pirate fun might be just what the ship’s doctor ordered. I was a skeptic at first, and was talked into participating – albeit reluctantly. But the joy and downright silliness of these pirates was infectious and completely won me over. Turns out, a little harmless rabble-rousing does the tired spirit a lot of good.

Pirate Sail 2019

If this sounds like fun to you, mark your calendars for September 14, 2019 for the next edition of the NYC Pirate Sail. That gives you plenty of time to work on your costume, and round up a motley crew to take to the high seas – or the Hudson – for a day of pirate merriment. You’ll be glad you did. Aaaarrrggghhh!

Pirate Sail takes the Hudson | 12° West

Pirates with attitude. Yours truly on the left. Photo: Todd Neville

Pirate Sail takes the Hudson | 12° West

This crew won the award for best decorated boat. Photo: Todd Neville

Pirate Sail takes the Hudson | 12° West

The crew of S/V Veronica from Sailors NYC goes to battle. Photo: Todd Neville

Pirate Sail takes the Hudson | 12° West

The beautiful S/V Arcadia added a touch of class to the Pirate Sail. Photo: Todd Neville

Pirate Sail takes the Hudson | 12° West

Water cannon battles in progress. Photo: Anastacia Stathakis Duber

Pirate Sail takes the Hudson | 12° West

Pirates take to the high seas. Or the Hudson, in this case. Photo: Todd Neville

Pirate Sail takes the Hudson | 12° West

The pirate crew of S/V Gitana. Photo by Anastacia Stathakis Duber

Pirate Sail takes the Hudson | 12° West

The crew of S/V Freebird with Supersoakers at the ready. Photo: Todd Neville

Pirate Sail takes the Hudson | 12° West

Pirates aboard S/V Arcadia. Photo: Todd Neville

Pirate Sail takes the Hudson | 12° West

Pirates enjoyed an after-party on the majestic S/V Arcadia. Photo: Bob Finkelstein

What does one wear on a pirate sail? We may need to work on some pirate designs for next season! In the meantime, our Saybrook Stripe Shirt in navy and red is a good option.

Many thanks to Todd Neville, Anastacia Stathakis Duber, Nitzan Levy and Bob Finkelstein for sharing your pictures of the event!