We have 5 days between Rome and a week with family in a villa NE of Florence. Plan to pick up a rental car in either Rome or Orvieto and see Orvieto. Definitely planning to spend at least two of those nights in/near Siena and probably one night in San Gimignano. But we are trying to decide where to stay for the first one or two nights. Options: Stay in Orvieto for one night, drive to Assisi, Cortona, or Montepulciano area...or add another day to Siena or add another day to Rome, where we would have had 3 full days. Background: First trip to Italy. Traveling in June 2005. Two adults and two teens. Don't mind the occasional one-nighter. See below for full itinerary:

Days 1-4: Rome (arrive late afternoon)
Days 5-6: Assisi or Cortona or ???
Days 7-8: Siena
Day 9: San Gimignano (see Volterra on way)
Days 10-16: Villa in Londa (NE of Florence)
Day 17: Pisa/Lucca (stay 1 night in Lucca?)
Days 18-19: Cinque Terre
Days 20-23: Venice

Fly home from Venice

I've never been to Assisi myself but I've heard it's gorgeous -- especially if you enjoy churches and mosaics. There you can see mosaics of the famous Italian artist Giotto, whose work is only found in Assisi or Padova (near Venice). You can't go wrong in Italy either way!

It sort of depends on how you want to spend those few days and what type of atmosphere you're looking for in between Rome and the week with family. It's true Assisi is worth seeing, especially the basilica - but of course it's very crowded in high tourist season, day and night. People will say Cortona is also crowded but the difference is that the buses leave in late afternoon and the evenings are pleasant. We stayed a week in Cortona (a villa about 2 kms. out in the country)in 2001 and intend to go back for a few days during a trip to Rome in October, and stay in town at the Hotel San Michele. We really enjoy the town's ambience and it seems to be weathering its fame brought about by the Frances Mayes books. I'd say go to Cortona, and then on day 7 as you are driving to Siena, stop over for lunch in Montepulciano.

bettyo70...

giotto never worked in mosaic and his works are all over italy. while the fresco cycles in assisi and padua are justly famous, he also worked in florence, milan and naples. his tempera on wood panels are legion and can be seen in several museums.

if you want mosaics try ravenna, venice and several towns in the marches who maintained a stronger trade relationship to the eastern empire and its more byzantine art influences.

sorry for the pedantry, but i'm sure you wouldn't want to misinform anyone.

Do not miss Assisi--seems like the best choice to me.

Thanks everyone. Bob, I just checked out your suggestion on another thread for Plaza del Capitano, so now I'm really wracked with indecision. Maybe we'll stay there and daytrip to Assisi... Of course, we have plenty of time to change our minds a few times before settling on a final plan.

Sorry, subcon and Carmen: I meant to type Giotto's "frescoes", NOT "mosaics." Was tired when I was typing my reply...

Yeah, same here. I meant Palazzo del Capitano, not Plaza...

Thanks 3gigs. I've been to neither, but hope to do this region next year, and your reason for choosing Cortona really rang bells with me. I had the same experience at Rothenburg-ob-der-Tauber. By day, impressive; by night, after the tour buses leave, pure magic. That's for me!

Everyone has their 'favorites', so I recommend that you read more on what each of those towns offer and make a decision based on what appeals most to you. If you are spending two nights in Siena (I hate to use cliches like 'gem' but it really is), you will get a good feel for it, so I would suggest spending one night in Orvieto, which would be an easy drive from Rome and you could leave early the next day and make a stop on your way to Siena. We liked Orvieto much better than Assisi. The town of Assisi was overrun with tacky shops, minimal Italian feel, average food, and we wish we would have spent just enough time to see the Basilica and move on. Orvieto was much more typical Italian, with locals doing the passagiata and having a drink before dinner, and great food. The underground Orvieto tour was fascinating too. Just my opinion.

If you are into churches, Assisi is wonderful. Yes, it is packed with tourists all day, but it is wonderful if you stay a few nights. The views are incredible. Most daytrippers just hit the Basilica for 20 mins and leave. I always go through the upper and lower levels of the Basilica in late afternoon. The tomb of St. Francis is quite moving, to make an understatement. Also gorgeous are Sta. Chiara, and five or six other glorious churches that most tourists never bother to visit.

I totally agree with Mariarosa. We thoroughly enjoyed Orvieto - had a great Italian experience - enjoying the culture - the people, food, sights, etc. However, the only thing we really enjoyed in Assisi was the Basilica - which was wonderful and I wouldn't miss it! But didn't see much else that was enjoyable - and thought the shops were so tacky. We enjoyed Spello right outside of Assisi much much more.

Twoflower, be sure to read the Frances Mayes books before you go, including the picture book/cook book that followed Under the Tuscan Sun - they will get you in the spirit of the place. When there, try the Trattoria Toscana for a long lunch or dinner. By the way, we had the same experience in Rothenburg - at night it was as if we had the place to ourselves - that is when we chose to walk on the walls encircling the town.

I think Orvieto, Assisi and Siena are not to be missed and worth at least one night each (notice that Assisi is a bit out of the way). Montepulciano is nice but doesn't compare to the above three. Also, note that Spoleto is close to Assisi and a very special town (preferred over Montepul. in my opinion). I love Rome the most, so even a 4th day in Rome might be considered.

I don't know Cortona or SanG or Lucca and feel Pisa is a big tourist trap.

However, I think you are missing the obvious opportunity to do some day tripping with the familly, from your Villa to see these other towns. Are you really going to stay put for a whole week at the Villa?

However it works out, home it is a great trip. I'm jealous!

No, we're not planning on staying put the whole time at all. But the villa is in NE part of Tuscany, in Londa, and I was planning to see some of the more southern towns and sights en route, rather than backtracking. (Our other family members that we'll be staying with at the villa were not especially interested in seeing the southern towns, but wanted to be close to Florence and have easy access to trains, which is why we're not staying at a villa in a more central location.) Also, while at the villa, we'll be daytripping into Florence at least 3 of the 7 days, as well as seeing some of the towns near there, relaxing by the pool, etc...

I really appreciate all the input from people who have been there. Here's my newest plan:

Depending on availability of rental car, either drive or train from Rome to Orvieto. See the sights, have lunch, and then drive to San Querico d'Orcia. Stay at Palazzo del Capitano for 3 nights, daytripping to Montepulciano, Pienza, Montalcino, etc.... Then stay in Siena two nights, daytripping to San Gimignano (late in day to outlast the tour buses).

As for Cortona/Assisi...I think we may see those, if we're up for it, on a daytrip/one night away from our villa. I think my mother in law would like that as well, and the kids could either come along or stay back at the villa by the pool.

Other ideas?? Keep 'em coming Thanks!

Carmen

Sounds like a very good plan to me. Have fun and be sure to eat at Il Vecchio Forno in San Quirico.

It's DEFINITELY on the agenda, as is the much touted place in Orvieto where the unexpected Fodor's gathering took place (The name is escaping me at the moment.)

Carmen, when you are in Assisi, make sure you visit the churches of St Chiara and St Rufino. They are not far from each other and although nothing like the Basilica, definitely worth a visit!

Topping for Kate12