The main phrase of our time spent in Tuscany was "Look at that cute little _______ (fill in the blank)." Everywhere you look, you feel like you are looking at a postcard. Tuscany is meant to be seen by car. You can go at your own pace and stop whenever you see something intriguing. There are so many small towns to explore it is hard to know where to start. I wanted to go literally EVERYWHERE, but I would suggest not doing that. I would pick a few key towns for a sampling of the different sides of Tuscany.
Now, if you are a fan of "Under the Tuscan Sun," you would go to Cortona. And, if you want to see a ton of "New Moon" and "Twlight" crazies, you might want to put Volterra on your list. If you are a none of those (like me), you would consider other options. Our itinerary was very loose. We had a few main stops in mind, but we took off driving and our itinerary ended up as follows.
1. Greve in Chianti: We really didn't see much of this town except for the beautiful land that housed our Agriturismo. Agriturismos are working farms that supplement their income by renting rooms to travelers. Our apartment was part of a 13th century farmhouse run by an adorable young Italian couple, Sylvia and Nameless. Nameless wasn't really the husband's name, but he never said it when we first met and after a while it was too late to ask. Sylvia and Nameless were the cutest Italian hipsters. They were a wealth of knowledge about local food and non-touristy sites. We were their first guests of the season and they welcomed us with open arms. We bought local food from a nearby grocery store and drank the wine produced on their land. It was incredible and I would highly recommend this for lodging in Tuscany.
2. Florence: Full of Renaissance art and architecture, this city is a must see. Just make sure you go on a day The Oil Shoppe is open. If you are sick of gypsies, go to less mainstream places like the Marino Marini museum or Boboli Gardens.
3. Castellina in Chianti: If you are wanting to see the Chianti region, this town is a great stop to see a perfectly preserved Medieval town.
4. Siena: The Piazza del Campo, home of the famous and historic Palio horse race, is reason enough to visit Sienna. Siena's historic center is beautiful with brick lanes, terracotta rooftops and Gothic architecture. We stuffed ourselves at a restaurant just off the Piazza, recommended by Nameless, of course. He said it was the only restaurant he would eat at in Siena. It was one of our favorite meals. Pricey, due to a language barrier miscommunication, but worth it.
5. Buonconvento: This tiny Medieval town is a quick stop on the way from Siena to Pienza. And, the drive there is utterly fabulous.
6. Pienza: This idealistic Renaissance town has a high terrace walk that is worth the trip. The town was beautiful, but I have far more pictures of the surrounding peaceful countryside. We could have sat on the terrace with a bottle of wine for hours. Why didn't we?
7. Montepulciano: Perhaps some of the most gorgeous views in Tuscany are seen from the walls of this Medieval hill town. This village is well-known for its famous red wine, Vino Nobile and there are many wine tasting opportunities here. When we were here, the streets and square were very quiet. We felt like we had the town all to ourselves....but not in a creepy way. This was a good thing when we found ourselves driving down a very narrow pedestrian street that ended in stairs. Thankfully, we were able to get out of that mess with no local witnesses.
Best drives through Tuscany:
1. The S-222 through the Chianti region connecting Florence and Siena: rolling grassy hills and vineyards
2. The SR2 from Siena to Buonconvento: Chianti landscape with tuscan houses/castles and cypress trees
3. The S-146 between Montalcino and Montepulciano: Classic Tuscany
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