Replace cold, windy, and wet with charming, romantic, and crowd-free to get the optimist's view of Boston in winter. Indeed, this may be the ideal time to visit, as there's plenty to do indoors, you'll have the attractions all to yourself, and you can enjoy cheap rates at area hotels and restaurant promotions.
Two of Boston's most popular winter events center on wine: the Boston Wine Festival and Boston Wine Expo. Spearheaded by acclaimed chef Daniel Bruce, the Wine Festival typically takes place at the Boston Harbor Hotel from January through April, with tastings, seminars, brunches, and dinners scheduled. Prices vary by event. The Boston Wine Expo will be held February 9 and 10 at the Seaport World Trade Center, and you'll be spoiled by all the choices—there are more than 400 wineries represented, and 1,800 vintages uncorked for sampling. A one-day advance ticket starts at $75.
There are also a host of possibilities for art lovers. Check out the latest exhibits at the new Institute for Contemporary Art on the up-and-coming waterfront (Thursday nights are free), or pretend you're in Europe with an afternoon at the villa-like Isabella Stewart Gardner Museum. If you want to visit both the Museum of Fine Arts and the Gardner, you'll get a discount at either by showing your ticket stub.
Boston's Logan is the most accessible airport to the city, although Providence's TF Green Airport can be used as an alternative, particularly if you wish to fly on Southwest. Search for hotel deals by visiting the websites of the Greater Boston Convention and Visitors Bureau, as well as the Massachusetts Office of Travel and Tourism.
It's no secret that winter is the most affordable time to visit Europe, and with the euro pummeling the dollar, every little bit of savings helps. It's an especially good time to visit Rome, as the tourist hordes won't arrive for months, and the weather (while wintry) is balmy compared to some locations in northern Europe, with temperatures reaching up to the 50s.
A big draw for a winter visit is "Le Saldi," the biannual clothing sales at designer and mainstream boutiques across the city, typically held throughout January and February. For fashionistas seeking a price break, this is more than enough reason for a trip. For other goings-on about town, including new exhibits, events, and more, visit the official Rome tourism website.
At press time, airfare from New York came in at $447 per person in January. For accommodations bargains, consider a vacation rental in or near the city. You can find extensive listings, organized by neighborhood, at VRBO.
You can also try booking a vacation package. Consider the offerings from go-today.com: A six-night package with daily breakfast starts at $729 per person for winter travel. That same vacation package more than doubles in price (to $1,559 per person) for early spring and summer trips.
Arts, wildlife, fine food and wine, and outdoor pursuits such as sea kayaking—all can be had with a winter getaway to Monterey. And while it won't be hot (winter temperatures range between 40 and 60 degrees), it's certainly pleasant enough that you can have an enjoyable time outside.
Start your explorations with the popular attractions: the Aquarium, Cannery Row, and Old Fisherman's Wharf. Beyond those, indulge your adventurous side with a hang gliding or skydiving excursion; try calamari stuffed, barbecued, or Sicilian style at Abalonetti's; or venture outside the city limits for wine tastings at your own pace.
For lodging, the Monterey County Convention & Visitors Bureau eSpecials website compiles current promotions from member properties. You can also find a good listing of area accommodations on GoMonterey.com.