If traveling to Tuscany, the small hilltown of Castellina is a great place to use as a base to visit the various hilltowns in Tuscany, AND to visit several wineries in the region.  The region is filled with wineries, large and small.  The Chianti region, and its hilltowns, are all connected with scenic, although often very twisting roads.  But, driving is relatively easy to reach any of its many wineries or other sites.  Many wineries in the region offer travele sthe opportunity to stop for a tasting of their wines  and a possible tour of their facilities.  Some charge a small fee, while others are free.  Most require an appointment, so it is best to check ahead on-line to see if your chosen wineries are open for tours and/or tastings, have fees, or require appointments.  Around Castellina, wineries that make for nice visits are La Castellina, Cecchi, and Rocca delle Macie.  Around Radda-in-Chianti, great winery visits are at Castello di Monastero, Castello d'Albola, and Castello di Volpaia.  A bit farther away, near the town of Barberino Val d'Elsa, Castello Monsanto offers a great program of tour and tasting.  Do some research and compare it with the schedule you wish to follow and hilltowns you would like to visit.  Then, see if there are any wineries nearby, or on the way, that pique your interest.  Then, go to that wineries website, where you should find information on tastings and visits, more often than not with English translation.  Salute!