Tuscany 10-day Itinerary November Help
 

We fly into and out of Milan. We've done Florence. Can do Venice another time. We are an innkeeper couple exhausted after a busy season. Want to spend time mostly in hill towns at a relaxed pace. However, we are good tourists, can do a lot of walking and have broad interests, architecture, art, and just being tourists. Want to see Siena, Volterra, Montelpulciano, Montalcino, Pienza, San Quirico, San Gim at night, Cortona. Maybe Lucca. And open to other suggestions. We prefer trains but accept the prevailing wisdom that Tuscany must really be seen by car.

(1) Need suggestion on where to go first after we arrive in Malpensa late morning.

(2) Suggestion for best place to rent a car. Take a train to Siena or Lucca?

(3) Best itinerary. Suggested geographical order. We have 10 full days plus arrival and departure days.

(4) Home base versus the possible romance of finding a lodging establishment on the spur of the moment and having some allowance to spend a couple or a few days in that place perhaps as a home base.

(5) Cinque Terre or any other place to get a hilltown feeling in a seaside area? We are coastal people at heart even if it's chilly and foggy.

(6) Where to stay on the way back to Malpensa for mid- morning flight back. Drop off rental car day before. Head to Milan. Lodging and transportation suggestions?

Thanks.

Hi Whitehall,

Just for starters, the Cinque Terre area is in Liguria which is a different state/district (I can't remember what they are called) than Tuscany.

I haven't visited Italy in November, but for that time of year and the places I've been, here is my commendation:

Train from Milan to Siena. Spend the rest of the afternoon and evening exploring Siena and stay overnight there.

Pick up your rental car in Siena the next day and drive to your first base in northern Tuscany to spend 4 nights and do day trips. These would include Volterra and San Gimignano, hopefully some of the Chianti area too!

Move on to southern Tuscany and stay 4 nights. Day trips to the southern towns and abbeys. Cortona is pretty far out of the way. It's very nice, but not any better than the towns in the more western area, Pienza, Montalcino, etc.

On your last day drop the car on your way back to Milan, maybe Chiusi, Pisa?

Spend your last afternoon and night in Milan seeing the sights. Of course, you could do this in reverse and see southern Tuscany first.

Another plan would be to spend your time in the Cinque Terre and Piedmonte areas. A whole different trip!

Hope this helps!

For us, the most convenient way to go is to (have the car booked ahead of time from the U.S. from gemut.com) pick up the rental car at Malpensa and return it there before our flight home.

I suggest a first stop at the Cinque Terre (about 3 hours drive). From there, Lucca and so on. I'd fashion a counter-clockwise loop route with Cortona as the last stop (how about Assisi too?) and I like your idea of finding spur of the moment lodging - you're off-season, so I think it wouldn't be a problem.

For your last night you should probably stay at a hotel near the airport so there'll be no hassle in making your flight.

Sorry for all the questions. Dayle, your suggestions are most helpful and we are trying to put together an itinerary that roughly follows your suggestions.

Tuck, we've done Assisi and Umbria. CT would be appealing if we can fit it in without rushing things and failing to get the local pulse anywhere.

Consider staying in Como prior to departing from Milan Malpensa.