Tuscany Wine and Hilltowns

Hello everyone, We are planning on arriving in Ancona, Italy from Croatia for an 8 day stay through Tuscany and ending in Florence. We love the idea of a wine and countryside vacation and would like to rent apartments versus staying in a hotel. Would you recommend staying in one place like Siena with day trips to places like Montepulciano, and San Gimignano or traveling the roads from Ancona to Cortona, Montepulciano, Siena and ending in Florence. Staying for a night or two along the way. Would love the advice. Thank you,

Posted by karren
oklahoma city, ok, usa
241 posts

I like to stay in one place and do day trips from there. Packing and moving to a new hotel each day is tiring time consuming. Siena is a perfect place to branch out from to visit the towns you mentioned.

Posted by Terry kathryn
Ann Arbor, Mi
3553 posts

Each person has their own travel style and some like to stay put and others like to hit the road. I have done both and for different reason enjoy both. If you have never done a 'road trip' in Europe and would like to try it, then Tuscany would be a place to do it. It's easy to move from town to town in Tuscany...find someplace you like and find a hotel. I would definitely not make Siena my home base with a car. Parking is frustrating and traffic can be heavy. If you want to pick a town for home base I would pick one of the others or someplace in the country and make your day trips.

Posted by Cat
Paia, HI, USA
141 posts

For the tuscany "country side" portion of my recent trip, i stayed 3 nights in Siena, (1 at a fabulous agriturismo JUST outside the city, 2 at a great inexpensive suites hotel that had a nature path down into the city itself). Both great - would've done 3 nights at agriturismo had I known more. Then I stayed 2 nights in Orvieto at hotel grande,Italia (fantastic) We toured Siena, Chiantigiana road (all the towns, a couple wineries), Montepulciano, civita de bagnoregio, and Orvieto over those 5-6 days. I liked 2 stays within tuscany\umbria,and didn't mind packing (2 stays for the week is ideal I think, 3 acceptable if needed) Totally different feel between the towns. If I were you, maybe San gimi/volterra a few nights, then siena a few nights. Although, Orvieto was fantastic! I wanted to spend a few nights in Montepuciano once we got there - it has an elegance, and many many restaurants, though I think I wouldn't spend more than a 2 nights there unless I were out touring with my car. I prefer having dinner, and walking home, so I can enjoy the wine, and see the night as I walk off my food!! Siena is more of a city, the others have a quaintness I wouldn't want to miss personally. Have fun! Oh- I'm a red wine appreciator, so I highly recommend the Chiantis, brunello, Sangiovese, Montepulciano... But the Orvieto White Classico is not to be missed if you're in the area!

Posted by Robert
Tampa, FL, USA
824 posts

Will you be renting a car or using the trains/buses for your transportion? if you rent a car, then travel the roads adn stay in some nice agritousimo's in different parts of tuscany. If you are not renting a car and will use the buses/trains then stay in a place like Florence (better conncetions) or Siena.