By Francis DiScala Jr and Jill Vasil:

Nantucket, the fabled island almost 30 miles off the coast of Massachusetts, home of summertime superlatives and quaintness that’s internationally renowned, is almost still asleep in mid-May. The spring thaw has finished and silently, simultaneously opens the manicured gardens and the wildflowers. Pickup trucks stuffed with mowers and ladders to prepare seasonal homes clatter on theMain Street cobblestone. The colorful street-clogging summer crowds haven’t yet arrived, and no tourists sporting Nantucket T-shirts abound. Some of the world’s greatest beaches are still here, but alas, all too cold to fully enjoy.

Even the weather feels colder than what New Yorkers and Southern Connecticutfolk see this time of year. Noticeably missing is much of the foliage and dense greenery seen here later in the year.

But what Nantucket does have in mid-May is wine. Lots and lots of wine. And a ton of fun people who are interested in learning about and tasting wine and good food. With this group of people comes an unmistakable civility that the younger Memorial Day partying crowd lacks, and that makes all the difference.

For two days across three sessions–12 p.m. to 2 p.m. and 3 p.m. to 5 p.m. Saturday and 3 p.m. to 5 p.m. Sunday–the Nantucket Yacht Club opens its exclusive membership and hands you a wine glass as you enter Wine Festival central (Reservations: (508) 325-4500). Instantly the vintners and their varietals fill the vision field, and the well-dressed and the festive render the excitement of the festival with approximately 165 wineries/exhibitors with their wares in attendance. Armed with the wine glass, you are encouraged, if not beckoned, to try all the wines and the foods. Vineyards put some of their best wines forward, and it is a real treat to anyone interested in learning about wine and food. Squid Ink cabernet catches my eye and I can’t resist the taste test. Tipping my head to pour in the wine, I notice chopped-up bars of chocolate on a cutting board. I finish the wine with a taste of Brix chocolate to be paired with wine. Delicious. Rows of tables displaying wines, food, All-Clad pans, bread, and other items overwhelm.

Many of Nantucket’s fine restaurants are in attendance, some offering cooking demonstrations. Pricing: $85 in advance for Saturday, ($110 from April 1, 2011); Sunday $125 ($150 from April 1); both Saturday and Sunday $160 ($190 from April 1).

2-3 p.m.
Price: $125
Location: White Elephant Dock
Host: Lyman Perry
Boat: Great Harbor Yacht Club motor launch

Well worth the price of admission is the wonderful launch ride piloted by a man responsible for some of the most notable newer buildings–both homes and clubs–of the island. Leaving the dock at the White Elephant, the boat heads north out of the harbor while 20 lucky guests sip wine–Pinot noir and chardonnay from Frei Brothers–and eat Kerrygold cheeses and butters from Ireland–while listening to the words of a man intimately familiar with the homes he talks about. Directing our attention to a large waterfront home, he points over his shoulder, “That is where a politician lives in Heinz’s home!” The harbor is a gentle sea and all the horizon speaks of history and of a day gone by: the whaling era of the 18th century. The homes have been preserved from necessity, rather than preference, as Nantucket is an island almost 30 miles to sea and all raw materials need to be brought in from the mainland. Viticulturist Jim Collins from Frei Brothers was on hand to help as first mate. Note: No high heels. Bring a sweater/raincoat.

Entertaining and delicious, a demystifying seminar on wine and food pairing was led by representatives of the Wild Horse Winery and Vineyard in the tent on the lawn of the White Elephant. Approximately 40 attendees were seated at white-clothed round tables opposite six glasses and a plate of five tastes: salty, sweet, sour, bitter, and the newest taste called umami (savory and round). Educating us on the tastes was a woman named Mikaela Sullivan, COPIA’s wine education manager, an expert who graduated with distinction from the Bordeaux Business School’s Wine MBA program. Also describing the wine was Clay Brock, the director of winemaking for Wild Horse. The white and the reds were exceptional, retailing at around $35 each. The group loosened up as the wine went down. Participation increased and the sun moved across the sky, sending flickering light across the waves of the harbor.

Many private homes open up to allow the vintners to entertain and host various parties. At one of these multimillion-dollar manicured estates, Veuve hosted a clambake, complete with lobster, clams, oysters, corn, cornbread, and, of course, champagne. Inside, outside, and poolside, we dined and enjoyed the cool afternoon into the evening, trying to appear polite while gorging on delicious seafood.

A must on Nantucket, American Seasons restaurant is on Center Street at the base of historic Cliff Road, surrounded by 18th-century homes. It has been a local favorite for years. The entrance welcomes with candle-lit ambience, and the dark wood, low ceilings, and immaculate details all create a style that hints of something special to come. In the world-class wine cellar, wines await to be paired with some of the best-prepared and most imaginative fare available on the island. We had a glass of wine and tasted some of the appetizers: sardines and pig ears, crispy like fries.

Union Street Inn is known as the best B-and-B on one of the world’s top resort islands, and the large home on Union Street is welcoming from the moment you open the front door. Built during the whaling era, the restoration with today’s taste and Nantucket feel gently calms and prepares visitors for vacation on-island. We did not overnight there but had breakfast in the light-filled garden-view table alongside the kitchen. Our omelet was light and creative, cooked with smoked cheddar cheese, fresh dill, and chives. The complementing coffee was served in a cup that I asked to bring home: a memory of a moment that seemed to hold still for longer than it actually lasted. The green ivy climbing the backyard wall and the light pouring into the garden kept me riveted to the seat while we spoke with Ken and his wife, Deb, the innkeepers, and learned of Ken’s shift from big-city hotel operations to co-ownership and management of what Travel + Leisure calls “by far the most stylish” of houses-turned-inns on Nantucket.

Each night we returned to our own home away from home in Madaket. Known as the starlight cottage, it overlooks Hither Creek. With its easy walk to the best beach on the island and amazing starlit skies (no light pollution out there in Madaket), the cottage is a nice retreat and a great place to stay if a beach cottage is your idea of vacation. To rent it see

Note: This trip was sponsored in part by Nantucket Wine Festival.




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