10 Days in Tuscany and Umbria: Best Two Towns to Stay In?

Day 1 Train to Orvieto (2 nts)
Day 2 Pick up hire car (7 day rental), excursion to Assisi
Day 3 Drive to a base somewhere in Chianti region or near Siena (5 nts)
Day 4 Excursion to Arezzo, Cortona
Day 5 Excursion to San Gimignano, Volterra
Day 6 Excursion to Montepulciano, Pienza, Montalcino
Day 7 Excursion to Siena, Monteriggioni
Day 8 Chianti to Lucca (2 nts), drop off hire car
Day 9 Excursion to Pisa
Day 10 Train to Florence

Wow! That's an incredibly detailed reply. Thanks, David.

Excursion days are suggestions only.
If you base yourself near Siena, you will find it is fairly central ...
North to Chianti region
South to Montepulciano, Pienza, Montalcino
East to Arezzo, Cortona
West to San Gimignano, Volterra

We spent five nights in Assisi and hated to leave. The magic of Assisi is in the evening after the daytrippers leave, and in the early morning as the locals cheerfully greet each other in Piazza Comune on their way to work. Sunset at the Basilica di San Francesco is unforgettable, as is looking down from the Basilica after dark to the lights of Santa Maria degli Angeli in the valley below.

Photos here.

Jonathan
I won't tell you the "best two towns to stay in" but I'd like to suggest two nights in Orvieto and two nights in Assisi. We could easily spend a week in Assisi. But that's us.
Enjoy the trip.
Gene

Thank you, Gene & Jeff.

Jonathan,
This may help with Tuscany http://www.slowtrav.com/italy/tuscany/hs_planning.htm

Look at Spello as a base in Umbria.

My home base for a year in Italy is Orvieto -- it is a wonderful ancient city and so is Assisi. Orvieto offers stunning views from the wall of the city over the valleys ... beautiful sunsets, and a quaint village lifestyle (once the busloads from Asia and America leave around 5:00). Parking a car is a challenge - if you rent a private apartment or house, look for one with parking. Otherwise, you will park in the big lot and take the escalator or funiculor up to the city. A bus provides continuous transportation to the city center with drop off at the tourist/information area in front of the magnificent Duomo (which is under exterior repairs now but will be gorgeous by next July).

Having lived in Orvieto since beginning of July -- this has been the hottest recorded summer in history. Many places across Italy do not have air conditioning. I would suggest:

• Book with air conditioning and reconfirm that it means your sleeping room has a/c
• If you have large luggage, be prepared to haul it yourself. Everywhere. REntal cars don't have huge trunks as they do in USA.
• Book a room off the main street unless you want to hear the 5:00 a.m. street sweeper, and 3 different trash pickups.
• Mosquito spray - Deep Woods Off in the non-aerosol will keep you bite free
• Check FlipKey for rentals of apartments and villas -- having the extra space, kitchen, and place to park is usually less than a hotel and within your budget!!! Have Google Translate handy -- look at the Italian listings - they are the best! I'm in a 2,800 sq ft palazzo apartment for less than $100 per night - and I am taking road trips throughout Italy staying in villas and apartments. The owners are typically very nice and very helpful and can help you arrange tours, guides, and stock the kitchen prior to your arrival.

If Andrea Bocelli plays Lajatica in 2016, book it! This year it was August 2 and 4th. Typically a Sunday (opera) and Tuesday (contemporary with guest performers) I recommend the "contemporary" performance over the opera. Splurge on good seats. It was one of the most magical nights of my life. Stay within easy driving and see Siena, Pisa and other special places in the area.

I love Italy!!!

Catherine

I would stay in Colle Val d'Elsa. it is between Siena and Florence. Perfect town to use as a base. Easy to get to all of the towns the one reply mentioned. Colle Val d'Elsa is a wonderful small walled town not very well known with the tourist scene yet. It has some very good restaurants and a wonderful bakery and the old town is an easy town to walk. If you go, stay at Palazzo San Lorenzo. you won't be disappointed. We've stayed there two of the times we have gone to Tuscany.
if Colle Val d'Elsa doesn't appeal to you stay in Orvieto, a beautiful town but much much larger than Colle Val d' Elsa.

Jonathan,
We stayed at Cretaiole Agritourismo Farmhouse last year near Pienza for a week and loved it. It's a great base for day trips to Montepulciano, Montalcino, Cortona and the many hill towns in the beautiful Val D'orcia area. The family running the farmhouse does a great job of meeting your needs and have many events planned during the week that you can choose to attend or do things on your own. I just can't say enough about our experience there.
Mike

I love Montepulciano -- you might spend a week in an apartment there; it is a good base for exploring the region and has lots of nice restaurants for evenings back in town. We spent two weeks there a few years ago with great pleasure. Here are some spots we visited in the area: https://janettravels.wordpress.com/category/tuscany/
Definitely spend a full day in Siena; the historic center is ringed by parking garages so it is an easy place to visit for the day. Climb the Torre Mangia and spend some serious time in the amazing Cathedral. It is lovely but not unique on the outside, but jaw dropping inside.

Assisi is a good place to stay. It isn't recent but we have stayed in St. Anthony's Guest House twice and really love it. Spare college dorm like rooms but with bathrooms but lovely common rooms -- library, lounge, lovely gardens, olive orchard. And we were able to park in the orchard. We really loved it. The place is run by English speaking nuns.

I vote for Orvieto and Montepulciano. And you can rely on RS Italy to find lodging within your budget in any town.

Terrific suggestions -- very specific, with detailed explanations. Thanks to all!