Chianti & Val d'Orcia Itinerary for Wine Lovers


New member
My husband and I are planning an 8 day anniversary trip to Tuscany in October. We are red wine lovers and have both already been to Florence, so we want to concentrate on the Chianti and Val d’Orcia regions, including a day trip over to San Gimignano and Volterra, and hopefully Cortona if we have time. We will be renting a car for our entire trip so transportation will not be an issue, and we definitely want to visit multiple wineries and vineyards while we are there. How much time would you spend in each area, and what cities would you suggest as a home base (preferably no more than two bases so we aren’t changing locations too much)? We really want to stay in the countryside in a farmhouse or villa to get more of the traditional, relaxing Tuscan experience, and although we want to see as much as we can, we want time to relax and enjoy a slower pace while we are vacationing. Any proposed itineraries and other suggestions would be much appreciated. Thanks!