Weekend Trip to Tuscany: What to do with 3 days in Tuscany

Trips to Tuscany are always popular. People always want to know which vineyards, towns and areas to visit in this stunning region. While it’s a region that I’ve been to a lot in the past, I haven’t explored it enough to feel like an expert on the subject. Instead, I figured I could give some tips based on my experiences in Tuscany and the most recent trip I took there before Christmas. Fall and spring are beautiful times to visit Tuscany because the weather is mild and you can do a little more exploring outside. Of course, the thing that I’m most focused on when traveling within Italy (or outside, let’s be honest) is the food. I filled up on pasta, cured meats and the best red wines while I was in northern Tuscany for the weekend. Here’s what we got up to and fit in over a three-day weekend in Tuscany:


Sightsee and enjoy a delicious aperitivo in Montepulciano

Montepulciano the town is famous for its namesake red wine, which happens to be one of my favorites. My boyfriend and I knew we wanted to stop here at some point, also because it was a on the way from Rome to Gambassi Terme, where we had our B&B for the night. The town did not disappoint and to my delight, we found a perfect spot for a late lunch/aperitivo as soon as we walked inside the walled medieval city. 


La Vineria di Montepulciano was so cute and cozy for a rainy day and had a fantastic meat and cheese board for a reasonable price. The glasses of house wine (Montepulciano, naturally) were also delicious and all of the food included on our tagliere kept us full until late that night when a midnight snack of tiramisu was very necessary. The food included was absolutely delicious and wasn’t limited to just the famous meats and cheeses of the region but also some fruits, veggies and great bread. To top it all off, the owner throws in a free pannacotta for dessert at the end to encourage good reviews on his Yelp page, which I was all about. 

We didn’t get to spend a ton of time in Montepulciano, so I would love to go back to the area around the town to do a wine-tasting at some point.

Relax with some terme at Gambassi Terme

After getting to our room in Gambassi Terme, which is both the name of the town and the nearby thermal springs, we did some research about where to get our terme on. I originally wanted a natural outdoor spring situation, but with it being November, everything seemed to be closed or didn’t have enough facilities for the chilly temps. We ended up going for the recommendation of our B&B owner, Enrico, who is such a gem. He suggested going to a nearby spa at Villa San Paolo and we absolutely loved it. We paid €22 a person for a three hour pass, either in the morning or afternoon, and you can utilize all of spa. This includes a relaxing area with tea and snacks, a large heated pool, pool-side loungers, a large Roman bath set-up with a sauna, steam room and a “wellness path” that takes you through 10 different stages of showering. It was a great experience and we left feeling so relaxed. 


I definitely recommend this spa and next time we’ll probably try one of the natural springs in the area that have the benefits of the thermal water, like this famous, free one in Saturnia.

Wander around some medieval cities

We took a short trip to San Gimignano and while I’ve heard of lot of good things about it, I didn’t love it. It’s definitely pretty, with some gorgeous views of the countryside because its a walled city on a hill, but the food situation wasn’t the best. To be fair, we also left lunch to the last minute (around 2:30/3:00) and found most places already closed. We ended up skipping it in favor of hot chocolate and pastries from a great bakery but found the whole city very touristy. I believe this is because of its central location and it being a popular spot for the Tuscany tours that many tourists opt for. 


Have the Tuscan meal of your life at Casa Masi

On our last night we knew we wanted to eat well and after EXTENSIVE research on my part (I really don’t like to take chances with a good meal) we came up with Casa Masi. This is one of the cutest restaurants I’ve ever been to, with a separate greenhouse and outdoor seating for warmer months and intimate fireside tables inside the main farmhouse. The food was outstanding. We split a great bottle of red, pasta with ragu (di lepre) and a Fiorentina steak too, which was insane. If you haven’t had this Tuscan speciality, get it done. I don’t even love steak but this was perfectly cooked (after I sent back a few pieces that were a bit rare for me) and so flavorful. I of course got dessert and finished with chocolate-covered strawberries. It was one of the best meals I’ve had eating out in Italy and I’ll definitely be back for round two. Keep in mind that reservations here are required a few days in advance.

So that’s how we decided to do a weekend in Tuscany and I loved every bit of it. It didn’t cover Florence obviously or the other amazing cities and towns all over the region, but it was a great taste of this part of Italy.

Let me know in the comments where your favorite places to travel in Tuscany have been and other recommendations for future trips! And be on the lookout for February's Dolce Vita Bloggers post next week.