Venere An online reservation service for hotels, B&Bs, country villas and other accommodations. Venere is an Italian-based company, so its listing cover not only major cities, but smaller towns, from Agrigento to Volterra. Useful maps let you search by city neighborhood.
Italian Tourism Office An Italian government office in New York providing information and assistance to travelers heading to Italy.
In Italy Online A comprehensive web site, with links to accommodations, specialized itinerary maps, advance museums reservations, car rentals & more.
Firenze.net Good portal site for all things in Florence: entertainment, restaurants, arts, accommodations (including hotels, agri-tourism destinations, and apartments).
Chianti Online Lists hotels, farm houses, restaurants, olive oil makers & things specific to Chianti region.
Context Rome For smart, thematic day tours in Rome and its outskirts. "The Renaissance in Rome," "Walk the Ancient Roman Walls," and more. Plus, tours of Tivoli and other famous gardens on the outskirts of Rome; even sailing tours.
Context Florence Comparable tours and services in Florence.
Context Naples Ditto in Naples.

American Wine Society A national education & networking organization, with local chapters and tastings.
Wine Brats Another national organization with local chapters and events, targetting Gen X wine buffs.
Society of Wine Educators A national membership organization of wine educators & people working in the wine industry.
Local Wine Events.com A collective listing of wine events in most major cities. Beer and spirits events as well. Readers can submit events or sign up to receive notification of local happenings.
Wine Institute A research, advocacy & information center.

A Taste of Italian Wine Culture: Wine bottling at home in Piedmont
A Visit to Castello Banfi: An American Giant in Montalcino
Everyone to the Table: Three Days at a Cooking School in Chianti
In Search of Farinata: Liguria's Ancient Comfort Food
Off to the Races: Behind the Scenes at Alba's Donkey Palio
Sicilian Wine Reborn: A New Breed of Winemakers is Shaking Up Sicily
Keepers of the Flame: Piedmont's wine heritage is alive and well at Renato Ratti
Tuscan Cuisine Meets its Match: Dinner at the Frescobaldi Wine Bar
Back from the Ashes: Resurrecting the Vineyards of Pompeii
Inside Gavi: Piedmont's White Wine Town

From the "Great Grapes" series in Tastes of Italia magazine:
Nebbiolo and the Allure of Barolo
Pinot Grigio: An American Infatuation