Going against all the recommendations for when to go to Italy we've decided to go for a month starting the middle of January. We've been to the big cities and Florence before and plan to fly to Bologna, eat ourselves silly for a few days and go south to Sienna. After that we have a few small towns in Tuscany and Umbria in mind and plan to work our way down to Sicily. The big question is whether to take trains and buses or rent a car or both which is where it gets complicated. Can anyone suggest an itinerary for this time of year without constantly moving and the best way to do it? I guess beaches and hill hiking will have to be left for a spring/fall trip. Guidebooks aren't helping much except to overload our brains with possibilities. Thanks so much for any and all help.
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San Francisco Bay Area (USA)
16238 posts
Too far to go to Sicily via ground transport from Tuscany. It's faster and cheaper to fly. Both Florence and Pisa have flights to Sicily with Vueling, Volotea, Ryanair etc.
January is cold, also in Sicily (although less so than elsewhere). Sicily has California type winter weather, therefore possibly rainy but not that cold, except at higher elevations. I recommend visiting cities with plenty of indoor opportunities (like museums, churches etc.). Palermo, Syracuse, Taormina offer a nice array of historical sights. Sicily is also rich with Greek and Roman ruins and archaeological sites, like the temples at Segesta, Selinunte, Valle dei Templi and Siracusa. They are outdoors, therefore they are not really that enjoyable on a rainy day. A car is not needed while visiting those cities. As in Tuscany, a car is however useful to visit those archaeological sites located out of town and also to visit the smaller towns (e.g. Erice). However bus and train options are available, they just require some more time and careful planning.