How to Win the Day

The pleasures of classic-yacht regatta charter

Steve Eddleston wanted to celebrate. It had been 10 years since he opened his first Planet Fitness gym, and he’d built the business up to 16 franchises in Rhode Island and Massachusetts. He was trying to figure out how to reward his trusted managers when a promotion for regatta charter aboard the restored 1939 schooner Eros landed in his inbox.

Eddleston, who came up sailing Hobie Cats and has a Corsair 780, thought a regatta charter aboard a 115-foot (35-meter) yacht sounded fun—but most of his managers had no idea how to sail.

The 180-foot Elena has claimed victory in regattas on both sides of the Atlantic.

“I think the trepidation at the beginning was quite normal, but as soon as we set sail, people settled in,” he says. “These people ranged from about 21 to 44, with a lot of them in their 30s. And they’re doing something for the first time that’s almost bringing you back to being a child. It’s adventure. It’s exploration. It’s pushing yourself to limits that you didn’t think you could do. I just think it’s the bee’s knees.”

Eros, which charters in the Nicholson Yachts fleet, is among a handful of larger sailing yachts available for classic and other regatta charters at events ranging from the St. Barths Bucket in the Caribbean to the Nantucket Classic Regatta in Massachusetts to Les Voiles de Saint-Tropez in the Mediterranean. Another yacht recently advertised for regatta charter is the 180-foot (55-meter) Elena, with Y.CO.

A regatta charter can create a real adrenaline rush when yachts come into close proximity, jockeying for position.

Capt. Stephen McLaren says that even aboard a replica racing yacht like Elena—built in 2009 from the Nathanael Herreshoff design of the early 1900s—no experience is required. Charter guests often find themselves excited simply to be in the midst of the regatta action.

“They just watch and film everything, and they’re entertained by what’s going on,” McLaren says. “There are 30 or 40 crew moving around the boat—very often, there’s 50 people on the boat, and 10 of them are guests. It’s a lot of activity, and even a very qualified sailor would be inclined to take a back seat and watch.”

Booking a large yacht with guest seating that’s separate from working crew areas is ideal for first-timers on a regatta charter, says Cameron Riddell, Eros’ managing partner.

“There are definitely boats that people should be scared of if they’re a newbie: Boats that are smaller, you’re going to have more motion, more sails and ropes in close proximity to the crew, you’re going to be in an intense spot on the boat, maybe even doing an important job,” Riddell says. “With Eros, it’s much bigger, so there’s lots more space, a lot less water flying around, and there’s definitely intense jobs for more skilled people—our crew does a lot of those—and there are places for people to sit and do nothing.”

McLaren says corporations such as Airbus have chartered Elena for a weeklong regatta, with different employees doing as much or as little as they pleased alongside the racing crew.

Note the way that Eros’ cockpit can keep guests out of the way of race-crew maneuvering.

“Every day, they bring different guests, 12 guests maximum a day,” McLaren says. “They were all put up at a five-star hotel at night and brought down to the boat in the morning, and they spent the day on the boat, then the next day they flew out and the next group would come in.”

Each charter guest receives the same custom regatta shirt that the crew wears, often bearing the charterer’s corporate logo, McLaren says. Those types of expenses, as well as the hiring of additional crew, putting them up in hotels and feeding them, means clients should expect to pay an extra 50 percent for expenses on top of a yacht’s advertised regatta rate.

Clients also should understand that different regattas have different flavors, Riddell says.

“The Antigua one is definitely the granddaddy of them all,” he says. “It’s a stunning place to be, the weather is great, and there’s lots of wind. In New England, the Newport Classic Yacht Regatta and Herreshoff Classic Yacht Regatta, those are great. But really, they’re all fun.”

Eros in a good wind with a bone in her teeth.

And no matter how much guests want to participate in boat handling by day, everybody gets to feel like a champion at night. Elena’s crew—all 30 to 40 of them—dine ashore at a single restaurant and invite charter guests to join them for post-race chatter.

Eddleston says his memories of the end-of-day camaraderie on Eros are among the reasons he likely won’t wait another 10 years before booking another regatta charter.

“I might do it the 11th year,” he says. “It was that good. You know, there are corporate team-building exercises; they take you to some reserve and climb jungle gyms or something like that. I think that’s OK, but to me, it feels very artificial and unnatural. This, being on the water, you have the wind blowing, it’s all just very natural. There are gorgeous ships coming all around and really close because you’re racing. They’re tacking, we’re jibing, you get a little education going. You have all the dynamism of the fleet, the colors of the water, the fun, and of course afterward there’s a little celebration. You pop a beer and go off to dinner together. If you asked any one of our crew what the most significant event they ever did was, this would be it.”

For more information: contact any charter broker.

  • Elena is part of the Y.CO charter fleet. Her weekly base rate for regattas with eight guests (racing only, not overnight accommodations) is about $114,000 with a provisioning allowance of about $57,000 for crew expenses, in addition to any guest expenses.
  • Eros is part of the Nicholson Yachts charter fleet. She offers two- to seven-day rates that match the number of racing and practice days in various regattas. Rates range from $28,500 to $54,000 for 12 guests and include at least one meal a day on board.


Contact our Charter team today for your next dream luxury vacation.