Wine & Countryside in Siena, Tuscany

As I began to do my research on Tuscany as part of our honeymoon, I had no idea how large the Tuscan region was and how many different areas there are to see and explore.  With that said, one could stay and explore this area for weeks and try a variety of wines, see historical sites, and access some great cities, including Pisa and Florence.

Where to Stay in Tuscany

My husband and I were flying out of Florence and wanted to do a night in the city before we left, so we chose to stay closer to the Florence, in the province of Siena, near San Gimignano, for our Tuscan countryside adventure. My husband and I found an Airbnb castle in Poggibonsi, called Castello della Badia. The property was historic and beautiful, with a pool and patios to relax. The host Nicholas was fabulous and had wonderful recommendations for the area, including restaurants and vineyards.

Castello di Badia Poggibonsi
Castello di Badia Poggibonsi
View from the back of Castello di Badia
View from the back of Castello di Badia

We rented a car to get here, and forewarning, the castle is on a steep and windy hill, so be comfortable in the car you are driving. If you are staying in the countryside, we recommend hiring drivers for your tours weeks to months in advance. We ended up having a tough time getting a driver to one of our excursions because they were all sold out for the week we were there. That said, we would definitely stay in the countryside again, as long as we have our drivers secured.

An alternative is to stay in more frequented areas and cities such as Florence, where hundreds of tours pick up and drop off from, to make it easier and more relaxing.

Tuscan Adventures: Wine Tour Recommendations

We barely scratched the surface of wine in Tuscany, but we had an incredible experience with every sip of wine we did taste in this beautiful area.

  • Fun in Tuscany. We ended up doing a Chianti tour through Fun in Tuscany and we would definitely use this tour group again. The staff are friendly, accommodating, and the cost of the tour is competitive compared to others (110 Euro PP). This tour does do day trips from Florence to Tuscany, but since we were staying in the countryside, we paid a small extra fee for a driver to take us on the tour with the tour group. We met some fabulous people on this tour as well! The tour included:
    • Tour and Tasting at Fattoria Poggio Allora, which is a farm and vineyard with beautiful views of San Gimignano. The wine tasting includes cheese, bread and olive oils and the experience is from a gorgeous patio overlooking the countryside.  The wine here is super affordable and worth bringing home a few bottles!
      San Gimignano view from Fattoria Poggio Allora
      San Gimignano view from Fattoria Poggio Allora
      Fattoria Poggio Allora Vineyards
      Fattoria Poggio Allora Vineyards
      • Visit to San Gimignano, which is a medieval village with great shopping and views of the valley. The history of the village is worth listening to, and some claim the twin towers were modeled after the historic towers in this village. Don’t miss out on the best gelato in the world on your stop.
        San Gimignano, Tuscany
        San Gimignano, Tuscany

        Gelateria Dondoli San Gimignano
        Gelateria Dondoli San Gimignano
      • Wine and food pairing at Tenuta Torciano, a slightly more upscale winery, with foods that served as a delicious late lunch. The winery itself was breathtaking, and even had a launch pad for helicopters. You can order wines and have them shipped directly to the United States here, which we definitely took advantage of.
        Tenuta Torciano Tuscany
        Tenuta Torciano Tuscany

        Tenuta Torciano Winery
        Tenuta Torciano Winery
  • Rocca Del Macie Tour and Light Lunch Experience. This winery is also set in this historic Chianti Classico area, and had a great tour and wine tasting set up for an hour, along with a brunch at their wine bar up the road (30 Euro PP). This winery was recommended by our castle host, and the wine was fabulous, winery was beautiful, and brunch was drool worthy, consisting of Tuscan cold cuts, cheese, and bruschetta, along with a full glass of wine! We would definitely do this again.
    Rocca Del Macie Winery
    Rocca Del Macie Winery

    Rocca Del Macie Light Lunch Experience
    Rocca Del Macie Light Lunch Experience
  • Wine Tour in Tuscany. While this tour did not work with our schedule for our time in Tuscany, the tour company had great reviews, and I have friends who had a wonderful experience. When we go back, we will be taking advantage of trying this tour as well! Donatella, the owner, does Chianti tours, as well as Brunello di Montalcino tours, an increasingly popular type of wine.

Pasta Making in the Tuscan Countryside

Our Airbnb host also recommended a fabulous cooking class through the Montese Cooking Experience.  If the weather is nice, the class is taught outdoors overlooking the beautiful countryside.  We had so much fun, and met people from across the U.S., Canada, and Russia in our small class of 8.  The class taught us how to make pasta, Bolognese sauce, ravioli, bread, and tiramisu, and includes unlimited wine. The class lasts about 3.5-4 hours, and is 135 Euro PP. My husband and I did get a private driver to take us to and from the class because this is also in a remote part of the countryside if you are not comfortable driving.

Montese Cooking Experience

If I went back to Tuscany, Italy

There is no if in going back to Tuscany, it’s just a matter of when. Tuscany was my favorite part of my honeymoon, a great mixture of relaxation, libations, and beauty.  When I go back to Tuscany, I will expand my trip to at least a week, take various wine tours, check out Siena, Pisa, and Cinque Terre, and visit more medieval villages along the way.  Who’s joining me!?

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