Stepping off the ferry in Nantucket is like stepping back in time. Once a bustling whaling village, Nantucket remains historically intact with cobblestone streets, towering church spires with chiming bells, and wooden colonial homes with widow’s walks, flower boxes and white picket fences bordered by blue hydrangeas. Men in Nantucket Reds, the saltwater-faded salmon-hued pants made famous on this island, Lacoste and polo shirts with upturned collars, and blue blazers accompany women in Lilly Pulitzer, Vineyard Vines and Talbots sundresses. This is the real deal: quintessential New England. And it’s here every May that the streets are packed with wine enthusiasts and foodies.
The Nantucket Wine Festival is actually a five-day feast of wine and food seminars, winemakers’ symposiums, special winemaker dinners hosted at and paired with local restaurants, and a charity gala and wine auction, centered around the weekend’s four-hour Grand Tastings held beneath a giant lawn tent harbqrside at the Nantucket Yacht Club, where more than 100 wineries are on hand to pour their best vintages. Special VIP purchase allows admittance into the Grand Tastings a half hour before regular ticket holders, and it’s well worth the additional fee to get in early, as the Grand Tastings are the most popular events and fill up quickly.
Select festival-goers arrive in time for Wednesday Night’s opening reception and dinner, but I arrived for a weekend stay in a gorgeous rental home, spending Friday evening at a private restaurant event that would pair five courses with wines from a specific vineyard. Celebrity chefs from cities like Boston and New York often host the dinners within welcoming restaurants , as well as private parties at stately homes. My restaurant of choice was one of Nantucket’s stars: American Seasons, which looked like it could have been a dining room on an old wooden ship due to its close quarters and wooden beams.
Easing my way into my second day — as many do after a wine-filled night — I took in a morning seminar about cheese, paired, of course, with wines and Champagne. Later that evening, I was treated to a wine cocktail reception at an art gallery before joining fellow art seekers for dinner at Company of the Cauldron, which was even smaller and more adorable than the night before, but equally delicious.
After dinner, it was a chance to get down at the After-Hours Grey Goose and Sweet Inspirations party, combining Grey Goose mixed drinks with chocolate delicacies. Held at a hip restaurant with an upstairs bar, the second floor became a stage for a stand-up comedy show while downstairs was a see-and-be-seen atmosphere complete with techno music.
It takes a little work to get to this island just off the coast of Massachusetts, especially in May as fog often closes the airport to Cessnas that hop over from Cape Cod, leaving passengers to wait for clear skies or a crowded ferry. But even with all the effort, Nantucket is well worth the visit any time of year, for time slows to a crawl and visitors hit true relaxation mode. But when Wine Fest rolls around? It’s five days of relaxation couple with great wines, good food and lots of newfound friends.