There is a lot to like about James Carmody, the bluff Irish general manager of the Seaport Hotel in Boston, even over the phone. Here he is, one of the founders of the Boston Wine Expo—the largest and longest running wine festival in New England (always held over Presidents’ Day Weekend)—an unabashed guy from Dorchester ("You can hear it in my accent") whose mother discouraged alcohol, but who is now a wine lover, and he's laughing at the improbable success of the event.

He was among a small group, most of them from the Boston Oenophiles Guild, who started the event in 1991 as a Hail Mary. The Guild members were interested in putting Boston on the wine map and Carmody was, too—he came up through the food and beverage side of the hotel business—but he also had a slightly more urgent agenda: to create hotel traffic at a dead time of year. Who goes to Boston in February for fun? After all, Carmody was working at the Boston Harbor Hotel at the time (in the late 80s), and the hotel would actually have to lay off banquet staff and "hope they'd come back in the spring," he says. 

"Still, the vision was always to make The Expo, which takes place just down the street in the World Trade Center, into a championship game," he says. (The proof? People turn out even when the Patriots are in the championship—"Okay, they leave at four," says Carmody. "Why not?"). "But really only two or three of us believed we could make this happen when we started," he admits.

The other heart-warming aspect of The Boston Wine Expo is that it was all done on relationships—"a snowball rolling downhill," Carmody says. Guild members were enthusiasts and wine professionals, and they used their knowledge and relationships to bring winemakers to Boston in the dead of winter. Which is probably why the Expo, for all of the 200 vineyards and 1,800 wines that will show up and be poured next month, has, as its defining trait, a pleasing quirkiness.

The Wine Spectator New York Wine Experience is far grander and much bigger—an Inaugural Parade as opposed to the Expo's Memorial Day one. Carmody admits it, but even Thomas Mathews, Executive Editor of Wine Spectator, gives the Expo credit: "It began as a something of a drinkfest, but has evolved for the better. The quality of the exhibitors has significantly increased and the seminars are serious educational offerings showcasing top regions and wineries. The attendees are a broad cross-section, including consumers just beginning to learn about wine, seasoned collectors, and veterans of the trade."

The Boston Wine Expo is reasonably priced, as the goal has always been to "keep it accessible." Therefore the entry fee is just above happy-hour prices in Boston (this was a legal requirement, as well). But, of course, there are events (last year, a Pappy van Winkle bourbon tasting), seminars, and a private lounge, all of which cost more but are still not in the 1%-er category. The overriding spirit remains "to develop the next generation of wine drinkers as part of a healthy lifestyle," Carmody says, which was part of the founding vision. The other key phrase: "Offer a spirit of discovery."

So if you fly into Boston on Tradewind’s scheduled private shuttle over Presidents’ Day weekend, you get to sample some brilliant—and hard-to-find—wines at a sizable discount.

There's Château Picque Caillou, a stone's throw from Pape Clément and Haut-Brion, a wine that I bought when I was earning next-to-nothing as a magazine editor and that turned out to age brilliantly. André Shearer, head of Cape Classics, a pioneer importer of South African wines (and former fashion model), will be there. As will Bertani, a great Amarone house—"They just won't compromise," says Carmody—and Domaine des Baumard from the Loire Valley, whose Clos du Papillon is a fetish wine. "I saw an older bottle at a retail shop and bought it knowing nothing," says Carmody. "Then I called the distributor and bought the rest." (You gotta love this, right?)

Among the highlights of this year's Expo will be “The World of Sicilian Wine” seminar—taught by Master of Wine Bill Nesto—a vertical of Chateau d'Ampuis led by Fred Ek—distributor of hall-of-fame European winemakers (Guigal and Remoissenet, among them)—and a Riesling seminar.

Regarding the latter, Carmody is 110% himself in admitting "We all grew up on Blue Nun as the transition from pop [soda] to wine."

But he's grown up—matured, one might say—just like the Expo: "Riesling is probably the greatest food wine there is.”

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Fly into Boston with Tradewind Aviation, offering scheduled shuttles and private charters from across the Northeast, including New York.

*All images courtesy of the Boston Wine Expo