Day Tripping in Tuscany

Day Tripping in Tuscany

by Ellen D.

Tuscany is home to historic villages, a food culture second to none and celebrated vineyards, which along with the beauty of its countryside make it a popular vacation destination. Most people have heard of celebrated Tuscan cities like Siena and Lucca, however there are a lot of smaller, lesser known towns that are equally magical, and I decided to spend a few days exploring these towns to better understand what day trips would be of most interest for clients staying at Wimco villas in Tuscany.


I began my trip in Grosseto in Maremma, with a plan to end up in Montalcino. The towns, and castles, and wineries along this route are bound to catch your eye as you drive through this area, so it is best to just head out and be willing to stop in areas of interest along the way. My first diversion was the little town of Paganico right off the highway (SS223) exit for the road to Montalcino. It was a quaint walled town that is enjoyable to drive through. I also couldn’t help driving though the medieval town of Sasso d’Ombrone and the hill town of Saint Angelo in Colle. As I continued on through the green valleys, I kept getting a glimpse of what seemed to be a large castle on a hilltop. I decided to head that way and was pleased to find it atop a hillside of covered with vineyards. The castle itself used to be a private residence, but it is now owned by the Banfi winery where they make a celebrated Chianti Classico Riserva. You can spend a full day here, starting with a winery tour in the morning (by reservation only), then a wine tasting and lunch at the taverna which had a nice menu and really lovely interior. There is also a glass museum housed in the castle and a more formal restaurant with great views for dinner.

Based on a recommendation from the gentleman pouring the wine at Banfi, my next detour took me see the church of Sant’Antimo, a beautiful Romanesque church built in the valley. As you travel these roads you will stumble upon plenty of small wineries that are open for public visits, whose wines would rarely make it out of the region. Visiting some of these local wineries feels like you have discovered hidden treasures.

I eventually made it to Montalcino, a beautiful village set on a hill, home to a celebrated red wine of the same name. I was long overdue for lunch and chose a nice wine bar located on a busy piazza, Osteria le Potazzine, to have lunch and a glass of Brunello. It’s a fun little restaurant where the walls are lined with wine bottles, and they attach a label to your wine glass so that you know what you are tasting if you decide you would like to purchase a bottle. I had the pasta called Pinci which is a specialty of Montalcino, and it’s delicious!

One can easily plan a day trip to Montalcino from these villas: HII NTISAL LAV


The Chianti region is probably one of the most well-known Italian wine regions. This area has a markedly different feel from the lush coastal area. Here the vineyards are set in rocky hillsides and your drive on the scenic S222 will take you through foreseted hills. The best bet in this area is to take your time, drop in to a few wineries that greet you along the route, and keep an eye out for a cute cafe. There are 4 towns within a short distance of each other that I drove through, Castellina in Chianti, Radda in Chianti, Panzano, and Greve in Chianti. All great choices for a lunch, walk or wine tasting.

I spent most of my time in Chianti in the village of Greve which is set along the banks of a river. Its main focal point is the busy piazza Matteotii where I was lucky enough to catch a small local festival going on. I stayed in Greve for the night and asked the hotel front desk for a restaurant recommendation. The owner walked me to his favorite pizza place in town, Via Veneto, that he said is only known by locals. He was right, I was only the third table seated, but by the time I left it was packed with families and groups of friends, and the food was excellent and cheap!

Fresh Seafood in Greve Piazza, Tuscany Villa Rentals, Italy Villa Vacations

There are some nice shops for souvenirs in Greve including one with locally made wood products. This is also a great spot to pick up groceries for the villa! There is a large meat and cheese shop, a fantastic bakery, wine shops, and a small grocery store all around the main square. While I was there, I also saw a seafood truck come into the square and park.

Visit the villages of Chianti from these villas:  SAL MNA


The town of Volterra is just about an hour west of Siena. Along the way is Colle di Val d’Elsa which is a beautiful medieval town set on a hill. It is famous for its crystal glassware and art production. As I continue on driving I can see the incredible town of San Gimignano in the distance, its high towers reminiscent of Oz.

Volterra is most famous for its alabaster craftsman, but it also has several museums, churches, and ruins to visit. This would make a great day trip for anyone renting a villa in Siena, Chianti or Montaione. The parking areas are clearly marked, and from there you can walk around this pretty sizeable town. My first stop was at the Museo Etrusco Guarino which has an impressive collection of Etruscan artifacts, namely funerary urns.

Many of the shops in town sell alabaster, and several shops have the artists working right there. I bought a lovely Alabaster frame at a small shop where craftswoman, Gloria Giannelli was working right there in the shop creating the pieces. There are many choices for dining from pizza spots to sit-down restaurants. I grabbed a slice of pizza from La Mangiatoia to enjoy as I walked around town. If you are still in town around sunset, take the time to walk along the path that lines the southwestern side of the town. It’s a beautiful path with incredible views to the sea. I was so impressed with this town and would recommend it to anyone.

Visit Volterra from these villas: BRV GINBRV CER


Interested in more Italian adventures? Explore the villages of Tuscany here!


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