Exploring the Tuscan Hills
Visit the Medieval Town of San Gimignano
On our drive from Florence to Montalcino, we stopped in the hilltop town of San Gimignano. It is fun discovering Medieval towns on our travels! With the amazing views of the Tuscan Hills beneath us, we sipped on our morning coffee at Caffe Giardino. San Gimignano has 4 main streets leading to the center; each street with its unique flag colors. Souvenir shops lined the streets. The one with the chocolate fountain almost sucked me in, but I resisted. This quickly turned into a tourist hotspot with tour buses flocking in around 10am. San Gimignano is definitely worth a visit, but go early (or late) to avoid the crowds.
Drink wine, of course!
When in Tuscany, you absolutely must drink their bold red wines. Try the Brunello! Many vineyards offer wine tastings but know that most of them require booking in advance. This is a great way to taste the region while also seeing the production side of the operations.
Poggino Rubino Winery was our first wine tasting. It sits on a beautiful hill in Tuscany, just about 10 minutes from Montalcino. The owner immediately introduced herself to us and the tour of the wine cellar began. If you are a wine club member, you are treated to discounts and priority access to select bottles.
After the tour of the wine cellar, we sat in the terrace and began our wine tasting. This was paired with what they called a light lunch: charcuterie, homemade pasta, and cake. A full lunch to me!
Tip: Ask to try their 16-year aged balsamic vinegar! It was absolutely amazing. I wanted to buy a bottle, but it cost 90 euro.
This was a fun experience in a lovely setting. Be sure to book a reservation and expect to be there about 2-3 hours.
Stay at an Agriturismo
An agriturismo is a great way to spend your holiday in Tuscany. Basically, this is a small hotel on a vineyard or farm. Our 2-night accommodation was at La Ragnaie Agriturismo, just about 5 minutes from Montalcino.
If you are staying at an agriturismo, a wine tasting is probably a perk included with your stay; be sure to ask! We started with a free wine tasting with the owner upon check in. This was a fast, informal tasting in the basement trying a selection of their wines. I do suggest doing a formal tasting at another vineyard (or 2 or 3) during your holiday.
Another perk was simply enjoying their beautiful property in the countryside. We spent an entire day soaking up the sun at their pool overlooking the incredible Italian landscape. Paired with some wine, it doesn’t get much better than that!
Breakfast was included, but meals were not offered at other times. The receptionist was very kind and suggested local food options for lunch and dinner. She called and booked the reservations for us. Both suggestions were fantastic! (desribed below)
Visit Montalcino
Montalcino is a small, old, hilltop town and was one of the only places we visited in Italy that was not full of people. That was quite nice! It was conveniently just about 5 minutes from our agriturismo. Montalcino is a cute place to explore the cobble streets and eat at small family run restaurants.
Eat aged parmesan cheese at Ristorante Il Giglio
Reservations are highly encouraged for this family run restaurant in the heart of Montalcino. The owner’s family was actually having a family dinner at the table right next to us!
Whether you are going for the food, wine, or friendly service, you won’t be disappointed. Start with the parmesan cheese plate! It consists of 4 different aged parmesans, paired with honey. You can’t go wrong! Of course, you must try their pastas. Wanting dessert? Get the impressive video worthy chocolate ball with hot salted caramel sauce poured on top! Mmm.
Choose your Florentine steak at Il Pozzo
This was another recommendation, but specifically for their Florentine steaks. Eating a Florentine steak was on our bucket list for Italy and saved it for the last night. Somehow, I didn’t get a picture of it before it was cut! It was priced at 50 euro per kilogram. After you place your order, they bring the slab of meat over to you and you must ‘agree’ to it before they cook it. We said yes.
Il Pozzo was a beautiful outdoor setting with amazing food. Definitely recommend this spot! For dessert, we had tiramisu and biscotti with some sort of liquor. This was an incredible last dinner on our Italian adventure!
….and that concludes our Italian road trip. From Lake Como, Bologna, Florence, and Tuscany, we saw history, drank fine wines, ate endless pasta, and truly had an incredible time. We are so fortunate that Jim was able to visit and enjoy this adventure! Thank you for this amazing time!
Where to next? A Mediterranean Cruise on the Celebrity Beyond!