My "to-be husband" and I will be visiting Cortona as part of our Italian honeymoon. We're looking into taking a side day trip from Cortona as we will have a rental car. What are your suggestions? We were thinking of Montepulciano, Montalcino, or Arezzo.....what are your thoughts? Anything we definitely must see?

Thanks as always!

Stacey

Both Montepulciano and Montalcino are great day trips. The latter of the two is a further drive. Pienza is another 20 minutes or so from Montepulciano and is definitely worth including. I can't speak of Arezzo as I haven't been there...hope this helps. Happy travels & congrats!

Any of those would make nice day trips. We just stayed 3 days in Montalcino and went to Altesino winery and had a GREAT tasting with pecorino romano cheese and prosciuto there. You can book the winery tour and tasting on line.
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Why are you staying in Cortona if you want to visit the Mont. towns? Why not stay in south Tuscany?

You must see Siena and San Giamingnano. My wife and I were there in May 2004 and in 2 weeks, went to Positano and surrounding areas, took a train to Florence where we picked up a rental car and drove down to Siena, Using that as home base (Villa Scaciapensieri) we took in about 2-3 towns a day. Among them, Montalpulciano, Montacino, San G., Pienza, Cortona and more. I don't know how much in detail you want to visit in these towns. They are rather small, but wonderfully pictureques. Siena and San G. are among my favorites and shouldn't be missed. I think all these towns are nearby and close enough to visit from Cortona.

I am a great fan of Arezzo. It is a fun city full of really interesting art, architecture, parks, shops and fabulous food. I mean fabulous. Bakeries, candy shops, food shops, sandwich shops and wonderful restaurants.

Go to see the Piero della Francesca frescoes at the San Francesco church. Arezzo will be quite an easy trip from Cortona. You could easily also take in Monterchi and Sansepolcro, which also have great works by Piero.

On top of the hill next to Cortona is Castiglion Fiorentino, which is a lot like Cortona but without the tourists. It has one main square and a few good restaurants and shops, and the views from up here are great!

Asissi is great, so is Montepulciano and Siena, and Arrezzo, Perugia -- it depends mostly on what you're looking for. Perugia has a great underground Etruscan city, but Perugia is also a big city. Siena is probably the one I've most often heard people talk about -- everyone seems to love it. Montepulciano is small and more intimate. Make sure you have a good map. Navigating in Italy can be difficult. We drove from Milan to Rapollo, to Levanto, to the Cinque Terra, to Pisa, Florence, through Tuscany and then to Rome. The autostrada is great, but once you get off onto the town roads, it can be confusing. Learn how to ask "Where am I?" in Italian and point to the map. Then say "This is where I want to go." Then indicate that you want them to draw on the map to show you directions. There are a lot of one way streets in some of the cities and streets sometimes change names every few blocks. Also, if you're from the States you'll need an International Driving Permit -- I think you can get one through AAA if you don't already have it.

Have a great time. Tuscany is truly beautiful. Take lots and lots of photos so you can sit at home and conjure up all those wonderful memories.

Cortona (truly charming) itself is a side-trip from the main destinations in tuscany ! -you must visit siena and san gimignano.