Caribbean Holiday

Sometimes the blizzards of the frozen reaches of North America meet their match in the whirl of holiday activity in the Caribbean. "Passage Notes" from our December 2009 issue

December 15, 2009

dec pn 09 368

Kevin and Peggy Gregory onboard Odyssey their Beneteau First 44.7 in the B.V.I. Elaine Lembo

The customer-greeting area at the flagship base of Horizon Yacht Charters, at Nanny Cay Marina on Tortola, in the British Virgin Islands, is a beehive of activity. It’s Christmas Eve, and receptionist Christalen Ambrose is cutting up the special holiday double issue of the Limin’ Times, a free guide to local events and entertainment that I worked for some 15 years ago, when I lived on the island.

As I recall, the holiday season was always a state of whimsical frenzy on Tortola, but nothing like it is now. Christalen is all business; on the counter in front of her is a binder with the title “Christmas and New Year’s Eve Events.” It’s loaded with news of more cocktail hours, fungi-band performances, midnight parties, and boat parades than a fleet of bareboat charterers and winter-season cruisers could possibly knock off. Still she clips away, and the binder gets fatter. “Sometimes it’s so hard to find out all the information,” she says as she works her scissors around another announcement, another ad. And so it goes; it’s the holidays in the Caribbean. Christmas winds of 25 to 30 knots have blown in on schedule. At the marinas, shiny garlands laced around poolside borders blind you in the hot midday sun; at night, multicolored lights twinkle and sway with rigging rocking in the breeze. Tropical holiday carols boom out of radios and iPods rigged up to speakers.

Woozy and happily weary after a narrow escape from one of Rhode Island’s more substantial blizzards, I wander away from the slip holding Flyer, the Swan 57 that my partner, Captain Rick Martell, sails throughout the territory when its owner is present.


My focus on this Sunday is the beach, and after a few minutes of lounging in the shade, I strike up a conversation with a friendly stranger, Peggy Gregory.

Poor Peggy: She’s nursing a broken toe she earned when she ran into a stanchion while fending off Odyssey, the family’s Farr-designed Beneteau First 44.7, from other boats.

She and her husband, Kevin, bought the boat new five years ago, she tells me. “The plan is to cruise the Caribbean through May. We’re calling it our ‘practice retirement.'”


Kevin’s business processes workers-compensation claims, and he’s able to get away and sail in the winter. “Because of the economy, we’d considered not coming, but there’ll always be workers-comp claims,” she says. “We decided to bite the bullet and do it now. Why wait until you pay off your debts?”

Back home, the Gregorys are active Great Lakes racers who hail from Buffalo, New York. They’ve done the Chicago-Mackinac Race, the Freeman Cup on Lake Ontario, and, on Odyssey, the Port Huron-Mackinac Race twice. They had Odyssey trucked to Annapolis, Maryland, from Buffalo; then a delivery crew sailed it to Trellis Bay, on Tortola.

Though the family’s spent previous Christmases in the Caribbean, bringing the boat down for the season presents a few new adventures for them, starting with the stay at Nanny Cay.


“We don’t have an exit plan,” Peggy says. “We’ve considered leaving the boat here. We’re seeing how much we really love each other this close, for four months, on a boat.”

When her son, Sean, stops by, I get a hint about how that’s going. “I was working on Dad’s work list,” he tells his mother. “I figure if I work half a day on a Sunday during vacation, that’s enough.”

Meanwhile, back on Odyssey and still deep into the chores, Kevin takes a break and puts it all in perspective.
“We’re lucky,” he tells me. “We have so much. There’s nothing we need, so it’s worth it to spend money to travel together instead of doing a traditional Christmas.”


Now well away from the beach, I continued strolling down the dock and came up short at a beautiful 72-foot yawl called Louisa, with a hailing port of Watch Hill, Rhode Island. Here, the crew of this Boretti-designed, Sangermani-built wooden beauty were far more preoccupied with surf than with holiday celebrations.

“We don’t get involved with the stress of the holidays and running around and buying presents for your family, one week before Christmas,” says the captain, Scott Simms. He and mate Nate Stone focused instead on the island’s north shore and the surf breaks at Carrot Bay.

When not surfing, they’re working hard to keep Louisa in Bristol shape.

“She’s a 40-year-old boat, so between systems and the varnish, we work nonstop,” Scott says. After Louisa fell off a cradle while being shipped from New Zealand, where she was part of the 2000 America’s Cup spectator fleet, her current boss bought her at auction and embarked on an extensive two-year refit. Scott’s sailed Louisa for five years, and I couldn’t resist asking this former poweryacht crewman if he ever gets bored. “Bored?” he says, incredulously. “Never.”

Louisa was once the yacht Tivoli, and she was renowned as much for her beauty as for her hull color. “It was a Grey Poupon yellow,” Scott says. “Pretty boat, but lousy color.”

In 1993, Louisa, as Tivoli, won the Antigua Classics Regatta. “She sails like a dream,” says Scott. Adds Nate: “It takes a breeze to get her going, but once she does, she goes and goes.”

My other half, Rick, is a friendly guy, and he eventually gets to know everyone on the docks. So he told me that before I headed back to Flyer to relax and have dinner with him, I was under orders to visit a friend of his, someone who enjoys a bit of renown both in the extended cruising community and one of its subsets, the world of wooden boats.

Indeed, Steve White, the owner of Maine’s Brooklin Boat Yard and a member of the board of trustees for the International Yacht Restoration School in Newport, Rhode Island, had landed at Nanny Cay for a Christmas celebration with his wife, Lisa, and her children. He’d shipped Vortex, his Knud Reimers-designed cold-molded Swede 55, down for the winter, and he’d be staying for a while before heading back to the dark and cold of northern climes.

White and Vortex hadn’t been to the Caribbean since the late 1990s, when he’d sailed the boat from Maine to Bermuda and on to Grenada, then worked his way back up through the islands.

“I haven’t been back in a long time,” he says. “I figured it would be nice for Lisa and the kids. I’ll try and spend two or three weeks a month here. I’ve got a great crew at the yard, so I don’t feel uncomfortable. We had a Christmas celebration before we came down, but we’ll have another one here.”

I wonder if the children miss the holiday in New England, which implies all the romanticism of a Norman Rockwell portrait but none of the icy hardship.

“It’s awesome here!” volunteers Collin Dupee, Lisa’s 15-year-old son.

Lisa says that it all came together for her a few days earlier, when they had a playful underwater encounter with dolphins while they were anchored off Jost Van Dyke.

Preparing for the trip and packing the boat with clothes and toiletries as well as other items for the kids was quite the organizational feat, she tells me.

“Even my paper tree from Barnes and Noble fell apart here,” she says. “But after that experience at Jost with the dolphins, that’s when I realized all the effort to get the kids down here was worth it.”

Though she might prefer the B.V.I., Elaine Lembo, CW’s deputy editor, spends most of the long, dark winter in the slightly more challenging climes of southeastern New England.


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