places to stay in Tuscany and Umbria

Do you plan to drive, or do you need places that are convenient to public transportation?

We are planning on renting a car..

Sounds like our pattern: First trip we fell in love and planned the second trip almost on the way home. Now we live here! Our second trip we went to Umbria for 5 nights and stayed in Spello, a tiny town, rather untouristy. We did not have a car and while we made that work quite well in a month-long trip thru Italy, you can certainly cover more territory faster with a vehicle. From Spello we day-tripped to Assisi, Perugia, Spoleto, and spent a full day on a wine tour with Gusto Wine Tours. Mark was incredible and if you like wine, you will love this day! We stayed at Casa Spello, which was delightful. In 2010, our first trip, we stayed two places in Tuscany: Montalcino and Siena. Personally I would skip Siena in favor of a small hilltown experience like Montalcino. Great dining in Montalcino, and of course Brunello. Since you'll have a car, be sure to take the drive between Montalcino and Montepulciano. Gorgeous! we loved our B&B, Palazzina Cesara. We hiked both in Tuscany and Umbria. I can give you more info on that if you are interested.

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Terri,
This may give you some ideas http://www.slowtrav.com/italy/tuscany/hs_planning.htm

We left Siena yesterday and stayed at Albergo Bernini. We loved it. They really make you part of the family. We are in Assisi now. We are at the Camere Mariani Marini. We like it too. Rick describes it as very basic but we think it is quite nice. Our room has a fabulous view too.

I have to agree with Laurel. Siena just didn't grab us. Of course, we went there only on a day trip. I have found that I have loved almost any town where we have stayed overnight. We have stayed in Montepulciano on two different trips and really like it. Look at Politian apartments (minimum 3-night stay, I believe). We have also stayed in Assisi and it was fine. Spello is at the top of my list as a place to stay next time. We also really liked Orvieto and would like to return as we had only one night there before. Have fun planning!

You can't go to Tuscany and skip Siena altogether if you've never been there before. If would be like going to Northern California for the first time and skipping San Francisco. There are always people who may like or dislike certain popular places, but you have to try it at least once. Some people prefer to stay in small villages, like Montalcino or Pienza, others prefer to stay overnight in bigger frenzy cities like Florence (Florence in Italian is Firenze, which in fact sounds like "frenzy" when pronounced by an American). Siena is somewhat in between (a bigger town of 50,000 souls, but not quite a city). So choose the type of ambiance you prefer for your base (smaller or larger), but then don't skip Siena altogether. Siena is definitely a Must See place that deserves at least a day trip, if you have never been. You never know. When you come back you might actually be one of those who thinks that Siena is the best place you've visited.

Of course, it's really a matter of what appeals to individuals. Personally, I loved Siena (frankly, the only place I didn't like was Florence, except for the incredible art of course. Blasphemy to some, I'm sure, but there I said it!). We stayed at the Cannon d'Oro and liked the place and the location. But Assisi!! Oh my!! It was, by far, my favorite smaller city. Just beautiful. We stayed at the Hotel Pallotta, which I would strongly recommend to anyonesmall, but nice room with view. Good breakfast (if that's important to you). The owners were very gracious and generous; they even discounted our last day because we were leaving early and would not be having breakfast there. They also have a very good restaurant, Trattoria Pallottadelicious!! I'm sure wherever you choose to go you will love it! Buon viaggo!

I also stayed at the Pallotta in Assisi, it was great. They have a sister property, the Hotel La Fortezza. Very helpful staff (moreso at the Pallotta), restaurant is very good with discounts for guests of the hotel.

thanks for the tips! i am the writer of another post on here regarding a honeymoon in italy. i have been there twice already and would love to go to some hill towns. this post has been a great complement to mine and i am very grateful! i am going to keep checking back. Terri, enjoy your trip!

Thank you! This helps. We looked into Hotel Berti in Assisi. Has anyone stayed there? Also, thinking of staying at a castle outside of Siena.

Terri, We just returned from 3 weeks in Italy, and spent seven nights in Castellina-in-Chianti, a small hilltown south of Florence; and five nights in Montepulciano. We loved our stays in both places, and visited six wineries in Chianti, and four in the Montepulciano/Montalcino areas. In Castellina, we stayed at the Palazzo Squarcialupi, a place that a local guide we met on a previous trip recommended. Castellina is a great hilltown to use as a base to travel throghout the Chianti area, and the Squarcialupi is a great hotel to use. For wineries, there are over a thousand in the Chianti area. Get on the internet and look around. We had no problems in booking our visits with them except to arrange four schedule although some of our visits were arranged by people from the wineries we met at wine dinners here in Dallas. In Chianti, we visited (uasing short names here) La Castellina (owned by the people who own the Squarcialupi), Monastero, Albola, Volpaia, Monsanto. and Rocca delle Macie. In Montepulciano, we stayed at the Meuble Il Riccio, just off the Main Piazza in Montepulciano. Its well dicussed in Rick's book. It is a bit small, and a lot of stairs, but a great location another choice to look at might be the Hotel Duomo). It is harder to find wineries to visit in Montepulciano, as Vono Nobile just doesn't get the same press as Brunello of Chianti. We enjoyed tours at Azienda Dei and Avignonesi (one of the best winery visits we have ever had). In Montalcino, we visited Fattoria dei Barbi and Croce di Mezzo (the agriturismo we stayed at in 2004). Both little towns are great places to stay or visit. We think next time we will stay in Montalcino, just for the variety. Good luck!

Did someone mention honeymoon - hilltown - for Umbria check out Monte Solare here http://www.villamontesolare.com/. A splurge but a very special one.