Bucket List Adventures | Driving through the Tuscan Hills

While we were visiting Florence, we decided to take a day trip through the Tuscan hills in Italy. We wanted to explore the medieval countryside, enjoy local Chianti wine, & visit medieval Siena. After our full day of exploring Florence (see here for Part 1 & Part 2), the Tuscan Hills were a great escape to enjoy the views of the surrounding towns.

Chianti castles ... Italian Tuscany Hills ... The Spectacular Adventurer

We woke up early to head out & rented a car near our hotel at the local Hertz. We booked in advance to ensure we got an automatic car. Manual cars are standard throughout Italy and we were lucky we booked in advance an automatic to minimize any confusion during the rental process.

Chianti Wine Region ... Italian Tuscan Hills ... The Spectacular Adventurer

Wine Tasting in the Tuscan Hills

Chianti region ... Italian Tuscany Hills ... The Spectacular Adventurer

We first headed for the Chianti region to enjoy the local wines. The rolling hills sprinkled with vineyards & castle like villas was stunning. Unfortunately, it decided to rain in the morning throughout our drive.

Italian Tuscan Hills ... The Spectacular Adventurer

This didn’t deter us however, and we enjoyed the winding roads. Our first stop was a small, family owned winery called Poggio al Bosco. We booked our visit in advance and were able to sample 8 varieties, as well as their local olive oil. The wine was exquisite! As we tasted, we learned more about the region, the history of the winery, & even toured their production.

Chianti Wine at Poggio al Bosco ... Tuscany, Italy ... The Spectacular Adventurer

Greve, Italy for Lunch

After our wine tour, we stopped in Greve for lunch. This small medieval town was so quant with a central plaza and cute spots to eat, including the Ristorante la Bottega del Moro. The food in this restaurant was delicious! We ordered an assortment of pastas & entrees to share, as well as glasses of their house Chianti wine. The whole meal was a delicious taste of the region.

Siena, Italy

Italian Tuscany Hills ... Siena, Italy ... The Spectacular Adventurer

Our final stop of the day, was Siena. Located in central tuscany, this medieval city, was the perfect end for the day. The walled city dates back to Roman times and has a ton of history to explore. We parked outside the city walls and walked into the city. We first came upon the Piazza del Campo – the main square of the city that overlooks the 14th century Palazzo Pubblico and its tower.

Twice a year in this square the 17 districts in the city compete in the famous Palio horse race. The egg shape of the square makes it perfect for this race, but also for viewing the entire square and castle. After enjoying the view of the square, we headed for the main church in Siena – the Duomo.

Siena Duomo ... Tuscany, Italy ... The Spectacular Adventurer

The Duomo of Siena was started in the 12th century and completed in the 13th. At the time, it was planned to be the largest basilica in the country; however, due to numerous plaques and funding issues, the church never was completed to the original plan. Never the less, the cathedral was stunning! The frescos and marble inlaid floors were spectacular. Climbing to the top, we were offered amazing views of the city and surrounding Tuscan hill towns. It was the perfect end to the day.

Italian Tuscan Hills ... Siena, Italy ... The Spectacular Adventurer

Also visit: Florence Travel Guide & Venice Travel Guide



  1. May 3, 2019 / 1:53 pm

    These shots are so gloomy and spectacular! Love it.

    • Liz
      May 4, 2019 / 10:49 am

      Thanks so much! Was a fun day shooting!

  2. Bindu Thomas
    May 8, 2019 / 12:16 am

    I love the pictures. I am adding this to my travel list.

    • Liz
      May 8, 2019 / 7:05 pm

      Thanks so much! Tuscany was such a dream! The rolling hills, villas, & wineries were to die for!

  3. September 11, 2019 / 9:30 am

    I don’t know how I reached your web site but I am really happy to read a feedback on our winery, Poggio al Bosco! Thank you!

    • Liz
      September 11, 2019 / 10:36 pm

      I’m so glad you did! You have an amazing winery and we loved visiting! 🙂

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