Long Island, N.Y. Vintage Tours sells five-hour excursions in 15-seater vans. The trip includes stops at four vineyards, as well as lunch; tasting fees extra. 631/765-4689, northfork.com/tours, from $65
Hermann, Mo. DSK Executive Car Service has vans that hold six people and limousines for as many as 10. The driver will accompany you to the tasting room and then introduce you to the owners of the winery. 573/259-4500, dskexecutivecar.com, $60 per hour for a van, $80 for a limo, three-hour minimum
Willamette Valley, Ore. Grape Escape Winery Tours sells outings for groups of all sizes. The five-hour Afternoon Escape, to describe just one, includes stops at two or three wineries and appetizers along the way. 503/283-3380, grapeescapetours.com, $500 for four participants
Santa Barbara, Calif. The deluxe package from Wine Edventures (that's not a typo; the company emphasizes wine education) includes stops at four wineries, a picnic lunch, and a ride in a grape-colored minibus (805/965-9463, welovewines.com, $95, six hours). Another option is Cloud Climbers Jeep Tours, which also stops at four vineyards and serves a picnic lunch, but drivers take the back roads in yellow safari-style trucks. (805/965-6654, ccjeeps.com, $104, six hours).
Napa, Calif. On one of Napa Winery Shuttle's minibuses, you can visit as many as seven wineries in a single day. To make the trip even easier, the company will even handle wine transportation for you. Just fill out a delivery card, and the company will drop off bottles you buy at your hotel that evening. 707/257-1950, wineshuttle.com, $52, six hours
These are only tours for the regions that we cover in this article--other wine regions tend to have them, too. Ask at your hotel or the local tourism office.
As seen on TV! We've followed Don Draper for seven seasons as he's crisscrossed the globe, be it via Cadillac or TWA flight. As the final episodes air, we're taking you back to the Golden Age of travel with a 'Mad Men'-inspired vacation guide for retro-style trips to cities Don visited.