Which hilltown to see?

I'd vote for Assisi as well. Also, chances are if you go back to Orvieto it won't be as wonderful as you remember. (Time can enhance pleasant memories, I've found.)

We loved Siena and San Gimignano.

We loved Orvieto but I like to see new things. If you haven't been to other hill towns, you should pick a different one. Each town has it's own personality. You will be able to appreciate a new one and view Orvieto from a new perspective.

Linda,
Assisi is absolutely beautiful. We've been to both Orvieto and Assisi and quite honestly, they're both fantastic. When are you going? Day tourists are many in Assisi, but still well worth it.
Boni

Cortona is an hour's train ride from Orvieto. I stayed in Cortona last year and liked it quite a bit. It may not be as spectacular or famous as other hill towns, but I really liked its smallness, low-key atmosphere, beautiful valley views (which are at least as good as the one from Orvieto). The St. Margherita church at the top of the hill is lovely, It's very hilly, with only one flat street in the center of town, so you have to like to hike. The art and Etruscan museums in the town center are very nice (Rick gives them one star in his guidebook), there is a nice park (the Parterre), several good restaurants, and the La Dolce Vita gelateria is one of the best I've been to in Italy.

Cortona, Assisi, San Gimignano are all quite nice. I don't really see Sienna as a hill town since there isn't that much of a view, and its the size of a small suburb. My suggestion is go somewhere new to you; while its nice to see familiar sites, it probably won't be as fresh or interesting the 2nd time around.

You don't say if you have a car or are going by train. If a car, you can base in one town and visit 1-2 others per day. I'd suggest choosing among Todi, Spello, Spoleto, etc. for these day trips. You can find many hill towns mentioned in Rick and other guide books.

Thanks everyone for your suggestions. Boni, you have me looking into Assisi since it seems to be a favorite among everyone. We're thinking of going in Sept-Oct time frame so I imagine the tourists will be many. Yes, you are right Michael as far as not being as blown away with Orvieto the second time around. I found that to be the case in other places that I have come back to...so I should keep that in mind. I notice Cortona being a favorite. I also was considering that hilltown. We have time for spending 2 days in only one, so we'll have to be selective. We haven't decided whether we're taking the train or using a car...still under debate. Again, thank you all!

I also liked Orvieto very much, though I only spent one day there. I have been to Assisi twice once was a return visit to show it to our friends. I wasn't at all disappointed on the return. We had a great time and my friends appreciated that we could show them all the sites of the town without them having to take a tour. Also in the area and worth seeing in addition to Cortona are Arezzo and Gubbio.

Here's a vote for Montepulciano and Pienza...both distinctly different, yet closely located, very walkable, and picturesque.

We just got back from 3 days in Cortona.I have never visited any of the other hill towns,but I totally loved Cortona.It was beautiful,interesting,and the food was wonderful.If you do go there,I suggest eating at Osteria del Teatro for dinner,and Fufluns is great,too.

Or Castellina, Panzano, Greve (not a hill town, but in Tuscany), Castellina, Montalcino.

Each town has it's own character....many of them have specialty olive oil, vino, cheese, pasta that you will just love.

I don't think it's possible to be disappointed in any of the hilltowns (except the tourist trap called San Gimignano). Italians know what they are doing when it comes to enjoying life.

Enjoy and seize la dolce vita whichever town you choose.

Three other great hill towns are Assisi in Umbria and either Montepulcinano or Volterra in Tuscany. If you plan on having a rental car, Assisi and Montepulcinao are both great bases for exploring other nearby towns.

Has anyone been to Poggibonsi, a little north of Sienna? We are looking at a place called Casale di Vittori, I haven't been able to find anyone who has mentioned it on the R.Steves site. If anyone has been here please let me know what your experience was, I'd appreciate it!

Gee everyone, you are making this very difficult. I'll look into all your suggestions and have to make a decision. But like April said, I probably would never be disappointed in any of them. Thanks all...they are all wonderful ideas!

TM - Poggibonsi is not a hill town. That's why no one has suggested it.

I'd go to Assisi. Was there in May and even though it rained the whole time we were there we still loved it. The view from the hill top is wonderful even in cloudy weather. I'd go back.

We returned from Italy on the 16th, from a RS Heart of Italy tour. I agree Assisi was wonderful,and would have liked more time there as well, but Siena is so unique with the culture of the contrada, and beautiful too. I would want to stay in Siena, but San Gim can be a an afternoon trip. We actually liked Siena better than Orvieto...all a personal opinion, of course. Have fun!

I would pick one town as a home base and take day trips to some of the others. We usually head out towards a specific destination and end up stopping along the way at any town that looks interesting (which is most of them). We have explored many towns that I had never heard of - Rapolano Terme, San Quirico d'Orcia, Lucignano) and found them to be just as great as the famous towns. If you plan on just staying in one town, then I agree with the others that Assisi would be an excellant choice.

I understand the advantages of staying in one town and taking day trips.On the other hand that means you miss the evenings in many towns which in my opinion is the best time to visit.Towns like Assisi are packed in the daytime but very nice at night when the daytrippers leave.

I am on the Rick Steves Hilltown tour right now and I would suggest that you look at the schedule in the tour descriptions. Each and every town is fantastic!!

We're considering going to Soriano nel Cimino, which is east of Viterbo and south of Orvieto. Has anyone been there? It looks beautiful on www.discoversoriano.com, but Rick makes no mention of it....

If you want something non-touristy and have the time, we stopped in Murlo, off SP34, and it was very enjoyable. Their town square is tiny, but it was fun to mix with the locals as they gathered for Happy Hour. We could tell that it was a novelty for the town to have visitors. Totally not commercial, but for a traveler, not a tourist, a worthwhile stop.

Thank you all. You gave me a lot of places to consider.

We just returned from our trip, and I'd suggest staying in Siena and day-tripping to the other towns. Our favorite (small) hill town was Montepulciano, but Cortona was also very cute and relaxing (this was the closest one to where we stayed). We liked Pienza- it is a beautiful little town, but it is tiny. We only spent a couple of hours in Pienza and felt like we'd really seen everything there was to see.

We have friends who loved Greve (which is really close to Florence). We didn't make it there on this trip and they chided us for it on our return!

Of course, there are many we didn't get to see either- so have fun with your itinerary wherever you go!

Linda let me throw my hat in the ring.
We try to go to hilltowns every year and have for
9 of last ten years. We have been to Orvieto. We like quiet places to stay at night and visit busier places during day.
We leave in about 2 weeks for next trip.
For area you are thinking about we are spending 2 nights at Vignamaggio just out Greve in Chianti area, 3 nights in Montalcino (now our most favorite hilltown that has progessed from day visit, to one night to two nights and now to three nights) and 2 nights in Cortona.

Chianti area is beautiful, good wine and food, close to other towns to visit and close and easy to run into Florence for the day if you get the urge.

Montalcino is highest hilltown, very quiet, great restaurants and maybe best wine in Italy and some think in the world. It is very wine oriented.
Beautiful vista from almost all hotels. Easy to get to places like Pienza, Siena, Montepulciano for the day.

Cortona has gotten more touristy due to Ms Mayes but it's still a great hilltown, Compact like Montalcino and its fame has increased the number of good restaurants. It is also easy for day trip to Assisi or Perugia.

The most interesting hilltown to have an incredible transformation in our experience from day to night is to spend the night in Assisi. Some much day traffic. At night walking around it is so quiet you think one of the Franciscan monks might be old St. Francis himself.

Whichever you choose it is very hard to not enjoy.
We spent the first three trips staying mostly one or two nights so we could visit a lot of places in hope that we would really like a few. We pretty much liked them all, but the 3 above are ones we really like.

Have fun.

Can't comment on Orvieto as I have never been there but we have just returned from a month long trip and had a fanatstic time. We stayed awhile in Perugia and took the train or bus each day to Spoleto, Gubbio, and to Assisi and loved them all. It may sound like a lot but travel times are short and we found that a good day in each was sufficient..and we're fairly intense tourists! From Siena we took the bus to San Gim'...nice but very small and 1/2 day was enough we thought. Would have added Volterra that day but bus connections were poor. Think bus too (not just trains) as there are many more options we discovered once we were there. And for my money, I loved our day in Lucca...a train ride from Florence on our itinerary. We rented a tandem and cycled around atop the city's walls. Really neat!

Thanks you Skip & Denny....so much valuable information. Everyone's wonderful explanations of the hilltowns they've seen, makes it a very difficult choice to make. Just when I think I know what I'm going to do, another really great suggestion comes across and I'm back to researching again. But just want to say thank you all for your thoughts & ideas...I appreciate them all!

Linda,
On our recent trip to Italia we ended up in a small town called Monteriggioni. We had planned on stopping in San Gimignano on our way from Rome to Florence. However, our time was limited. So we spotted this city in one of the books we had with us and decided to stop. Well, what a great surprise. It is a lovely walled city which had several very nice restaurants in the town center. It had 14 towers and you could walk the wall and take photos. It was a nice discovery.
Here is a link
http://www.monteriggioni.info/

Linda,
we have just returned from Italy and stayed in Tuscany. Our absolutely favourite hill towns were Volterra and Montepulciano. Not as touristy but scenic and very classy, especially the latter. If return, and I did throw coins in the Trevi I would stay in Montepulciano and travel out from there.

I will second Monteriggioni, it was lovely there and not crowded. You can walk part of the wall and there are several restaurants in the main square. We didn't have time for San Gimignano and it was a pleasant surprise.

Montepulciano, Montalcino and Pienza - all great

Montepulciano is my favorite hilltown, then Pienza, then Montalcino. But, I think they're all great. Civita is DEFINITELY is worth visiting---it's actually in Lazio, but a very short distance from Tuscany. It's a UNESCO world heritage site-- quite spectacular and unique.

Linda, I see you have received a lot of good suggestions. I do think that if you like crowds of tourists by the busloads (and some delightful views) try San Gimignano. After multiple trips to Italy and Tuscany in particular, my wife and I are partial to Volterra and any of the small towns on the Chiantiagiana (SR222)between Siena and Florence. Montepulciano, SE of Siena, is a nice 1/2+ day stop - great photo ops and some decent wine tastings. The Vino Nobile may not be as outstanding as Brunello from Montalcino but it's nowhere as pricey either. If you are in southern Tuscany, you can try a few offbeat towns west of Orvieto like Pitigliano, Sovana, and Sorano. The Etruscan influence here is amazing. There are also some wonderful hill towns in Lazio like Tivoli (a bit touristy but almost all Italian daytrippers); Fiuggi (a spa town popular with Italians); Anagni, not touristy but historically significant and no foreign tourists, and Castel Gandalfo, the Pope's summer residence. A little further south try Monte Cassino (not the town of Cassino in the valley). The abbey is a cultural and historic gem and the views are breathtaking. A little to the NE of Cassino is the Val Di Comino and some beautiful hilltop villages not totally discovered even by Italian tourists. Hope this helps

Lake Como is like no other city in Italy, it is definitely worth the drive. If you can stay at Villa d'Este even if only for a few days it is the best place to end your trip. We started in Rome and drove all over, even went to the Ferrari plant, but ending in Lake Como was truly exceptional. The Lake is beautiful in May, the villas are beautiful to see. The grounds at Villa d'Este will keep you enthralled, and the food is magnificent.

There is great shopping for silk in Como, and you can easily fly back to London or the States from Milan.

We spent 3 weeks in Italy in Sept. on the RS hill town tour. Yes, Asissi is wonderful, San Gimmy, is fabulous, but really, it must be Siena! The culture is unique there, it is gorgeous, very special. Have a wonderful time!

Thank you Jean & Christine for your helpful comments. With all these wonderful suggestions, I might have to stay there indefinitely. Seriously, I appreciate everyone's suggestions and will be looking into all of them for our home base. Thanks!

Oh my goodness, I didn't see that there was a second page of even more great hilltowns ideas. You guys are making it very difficult...but what a problem to have. Thank you also Denise, Linda, Claudia, & Tony.

Hi Linda,
Karen Brown has a PDF guide to Tuscany that you can buy online for @ seven bucks. It has a great map and good descriptions of the small hilltowns (and equally charming towns in the Chianti) that augment Rick Steve's guides. It's nice for day trips.

I liked Montepulciano and Pienza, but they are all fun in their own way.