Assisi or Montepulciano

Just to make your decision making a little tougher, let me put in my two cents about another option: Siena. This was one of my favorite places on my trip to Italy. Large enough to keep you from getting bored but quaint enough to slow your pulse. We stayed at one of Rick Steve's favorite places, Albergo Bernini. Great location and a great terrace. We would just grab some cheese and bread or pizza and a bottle of wine and sit on the terrace and soak it in. Stroll over to Il Campo and have an appertif or a coffee and just sit and people watch.

I do not understand why you keep returning to Florence for 1 night. Seems that you are backtracking, and you will have already been there for at one point for 8 straight nights. (which to me is WAY too long in Florence!) To your question. Montepulciano is very small, Assisi is larger, more to see and do, and of course more crowded, probably more so in the summer months. I'm not the expert here, but I'd think you could take those extra one nights in Florence and spend those nights in both Montepulciano and in Assisi. Just some quick thoughts about your itinerary as presented.

Paige, I agree that 12 days in Florence is too many. I can't speak to Assisi because I haven't been there. But I will tell you that I spent a very fun and relaxing 3 days in Montepulciano this past Fall. Loved it! We stayed at Villa Mazzi which is right below the hill town. Check out their website. http://www.villamazzi.it/azienda.en.php The location also was perfect for short day trips to Pienza and Montalcino as well as the surrounding Tuscan countryside. We also made a great day trip to Cortona. There are several very good restaurants in Montelpulciano. For a good steak Florentine and a fun time check out this place: http://www.acquacheta.eu/english.html Since you say you are "looking for a slow, easy pace to just enjoy Italian life" you may want to check out this website for ideas: http://www.slowtrav.com/italy/

I've stayed in both Assisi and Montepulciano, and both are great hill towns. Assisi has much more to do, especially in the evening when people linger at cafes around the main square. Montepulciano would be a good choice if you want an even slower pace. I'd recommend La Pallotta in Assisi. It has a nice lounge area on the top floor with nearly 360 degree views, and you get a 10% discount at their excellent nearby restaurant. In Montepulciano, I'd recommend Meuble il Riccio. It has a beautiful lounge area and a nice rooftop deck. Breakfast is optional but worth the price. They also offer vintage car tours of the surrounding area (described on their website – best to arrange in advance). A couple who took one while I was staying there said they really enjoyed it. There's no need to break up your travel from Sorrento to Cinque Terre and from San Gimignano to Venice with a night in Florence unless you want to. As an aside, I personally don't think a longer stay in Florence is too much for an art educator and foodie. The food in Florence is my favorite in Italy. The art speaks for itself.

Thanks for the information! The reason there are 1 night stops in Florence is because I was concerned that a trip from Sorrento to Monterosso might be too long. I am not thrilled to arrive in a new place too late as I am a solo traveler. I want daylight to get aquainted and assess. The 2nd 1 night is the same sort of thought...Florence being a hub and I thought I might have to reach that hub to reconnect to move onto Vence. There is another reason- my daughter might come for a portion and I was giving space to have her arrive and depart from Florence as open jaws is more expensive.
I love the questions...it gets me thinking differently.

I too enjoy Siena for the same reasons you say. I have visited twice. We also stayed at Albero Bernini. It is simple and perfect. During our last visit we were there during the Palio. What an experience! My only issue with Siena is the location of the train station.
With this trip, I am just trying to spread my wings a bit more and explore new places.

I've stayed in both Assissi and Montepulciano, absolutely loved both but if I were forced to pick just one (very tough choice)... it would be Assissi. But I agree totally with Ellen, I hope you can figure out a way to stay in both. Very well worth it.

OK, I agree with Susan, except I would go with Montepulciano. And here is why, you said, "I am looking for a slow, easy pace to just enjoy Italian life not check things off a list. I am an art educator and foodie." In my opinion this town would suit you a tad better, but the fact is you can't go wrong either way. So that made things easier for you! (:>D

When we were in Italy in 2003, we found Montepulciano by accident. Thought we book a place in Sienna, but turned out to be a agritouismo just outside of Montepulciano. Well, we are going back to Italy again this September (now our third trip), and our itinerary includes 4 nights in Montepulciano. That's how much we enjoed the experiance. We will use it as a home base for day trips. Other options for you....Lucca. Great town. Instead of stopping in Florence for the one night layover ( I agree that the trip from Sorennto to CT is long), try stopping in another location you haven't been to.

I have taken the advice of many and chosen other towns to do my one night stops (Chiusi & Albenga) instead of returning to Florence. I love the fact that this forum can open my eyes with such thoughtful suggestions.
Mille Grazie!

I'd also vote for Meuble il riccio in Montepulciano. If the weather is nice, a drive to Lake Trasameno w/ a picnic would de a pleasant day's outing.