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Sailboat charter business finds safe harbor in the Hamptons  

Owner and operators of the sailing charter boat

Owner and operators of the sailing charter boat Sail Dauntless had to pivot their business plan when the pandemic hit. With original plans to set sail in Europe this summer, they are now chartering out of Sag Harbor.  Credit: Randee Daddona

With the pandemic about to sink their 3-year-old private cruise business, Jim and Judy Brown changed course — more than once. But their new Long Island headquarters presents its own challenge: a relatively short sailing season.

Confronting border closings in the Caribbean, their original base of operations, and the travel industry’s shutdown during COVID-19, Jim Brown steered the couple’s 55-foot Jeanneau sailboat, christened Dauntless, to the United States. They had planned to drop the hook in Annapolis, Maryland, before navigating to the Mediterranean.

"I’ve felt like I was a bus driver going up and down the Caribbean, so our goal was ultimately to go to the Mediterranean," Jim said.

But with COVID infections fluctuating earlier this year in Croatia, Greece and Italy, the Browns have relocated their company, Sail Dauntless, to Sag Harbor, where they are running private cruises this summer and fall, as well as next summer.

"We want to keep paying our bills," Jim said.

A native of Bangor, Maine, and retired corporate landscape architect, Jim, 65, is the boat’s captain. Judy, 57, who hails from Garden City, is first mate and chef and continues to assume projects as a landscape architect. They are the business’ only employees.

Although the pandemic last year fueled an 85% drop in the global charter cruise market, a quick rebound is anticipated for the sector. Easing lockdown restrictions and tourism’s resumption are setting the stage for a predicted 25.6% compounded growth rate between 2020 and 2028, according to an industry analysis from Zenadian and Research and Markets.

Newsday spoke with Jim about the seafaring couple’s charter cruise operation, including the rationale for mooring in Sag Harbor.

What are Sag Harbor’s pros and cons?

Sag Harbor has advantages for a charter cruise business, including close proximity to Nantucket, Mystic or Newport en route to Boston. But it’s basically a 90-day sailing season because after that it’s too cold, and kids are back in school. The Caribbean is 85 degrees year-round but a six-month season because of hurricanes.

What charters do you anticipate being the most popular?

Since this seems to be a weekend market, the calendar will probably be filled with half-day, sunset and two-night cruises completed on weekends.

How much does a private cruise run?

Trip prices range between $1,500 for a 2.5-hour sunset cruise for two to six guests and $13,500 for a seven-day trip for six passengers.

What’s the most interesting local booking so far?

We’re taking parents, along with their teenage daughter, to watch their son in multiple Newport sailing races. We’ll be a spectator yacht.

How do you handle a storm?

I subscribe to five weather services and review them each morning and the night before sailing. If a sudden thunderstorm creeps up, I’ll go to the closest safe harbor, which doesn’t have wave or wind action, to minimize sudden impact. I’ll also reschedule if a thunderstorm is coming. It’s always about guest safety and having a good time.

How are you promoting your Sag Harbor arrival?

Our efforts include ads in travel magazines, complimentary sailing for influencers and direct marketing to select ZIP codes within easy driving distance to Sag Harbor. We’re also listed with a global cruise clearinghouse that matches clients with yachts and crews. And we’ve reached out to upscale hotels in the Hamptons, which have been extremely receptive to showing our rack cards to guests.

After Sag Harbor, what’s next for Dauntless?

We want to spend about three years sailing in the Mediterranean and then go to the South Pacific. We love to entertain, and our goal is to travel the world.

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