Tuscany is a central region of Italy, known for its Renaissance art, architecture, wine, and food. The art cities of Florence & Siena are very different from the countryside towns. We enjoyed our time more in the countryside enjoying the quality products and exploring the hilltop medieval towns. This is how we recommend you spend your time in the countryside.

Wineries
Iconic Tuscan Road
Passignano sul Trasimeno
Lake Trasimeno Boat
Montepulciano
Cortona

Wineries

From Florence we drove South, passing some amazing wineries. We were limited for time so we couldn’t stop at every winery or olive producer that we liked the look of. After research, we decided the best winery to visit and buy Chianti wine from was Barone Ricasole. There is a castle next to the Winery called Castello di Brolio. We did a wine tasting which was free because we bought over 100 Euros of wine. We joined the wine club and got 10% off. We were very delighted to find out that delivery to Germany is only €7.

The winery restaurant (Osteria di Brolio) had just closed the kitchen at 2 pm like most restaurants in Italy. So we went back to the Wine Shop and a friendly worker called a highly recommended restaurant nearby called Trattoria il Carlino d'Oro. They kindly agreed to keep the kitchen open for us. It was a small family restaurant on a hill overlooking the surrounding vineyards. The food was delicious and reasonably priced. The olive oil at the restaurant was superb.

We looked up the olive oil and it came from a wine and olive producer called Azienda Agricola Vallepicciola. We were searching for some Rose to buy so we made a short detour and visited. The winery was unique for the region as it was a modern architectural masterpiece and the vibrant rose was produced from Pinot Noir. We would have loved to do a wine tour around the large estate if we had more time. We bought olive oil and 6 bottles of the Lugherino Rosato. The olive oil was perfect to have with bread and the Rose was the best we’ve ever had. We even got some more Rose from a supermarket in Siena on the way back to Germany.

Iconic Tuscan Road

This iconic Tuscan road winds through the beautiful wine country. It’s next to the entrance of Agriturismo Baccoleno which is around 6 km south of Asciano. We parked our car on the side of the road with other cars and had a short walk to the spot.

There wasn’t a cloud in the sky and we got there 1 hour before sunset. It was truly magical and romantic with this view! Bring a picnic rug and a bottle of wine for a romantic sunset date. As it got closer to sunset more people started to arrive and more drones flew overhead.

Another beautiful spot for photos is on the tree lined road.

Where to stay in the Passignano sul Trasimeno?

After following the detailed directions, we arrived at the remote Villa Casa Campori and were greeted by our Aussie friends now living in London, Hugo and Maddie. The villa was located 15 minutes drive away from Passignano sul Trasimeno, and a 2km drive up a gravel road from the main road. Therefore it was very quiet and relaxing, especially next to the pool.

Hugo and Maddie were responsible for purchasing the quality Tuscan food and we were responsible for the drinks. Therefore, we could enjoy the outdoor dining area with a view over Lake Trasimeno instead of going to restaurants. The kitchen had everything we needed and outside there was a pizza oven and bbq grill. At sunset, we had the perfect view of the sun going down behind Lake Trasimeno.

Passignano sul Trasimeno

Passignano sul Trasimeno is a small town located on Lake Trasimeno, in Umbria near the border of Tuscany. We walked along the lake and explored the old town.

Lake Trasimeno Boat Hire

We visited the harbour at the beginning of our stay and booked a small motorboat for 2 hours at sunset for a day when the conditions were good. The company is called Passignano Rent Boat. It only cost us €90 plus petrol (approx. €20). The boat had Bluetooth and speakers for music. We found 2 idyllic spots to put the anchor down at, an island called Isola Polvese and a castle called Castiglione del Lago. We relaxed, listened to music, swam around the boat, watched the sunset, and enjoyed drinking beer and wine that we took on board. The wind picked up on the way back to the harbour and it was a very bouncy ride.

Cortona

Like many towns in Italy, you can only drive into the city if you are a local resident or have a permit. We drove as far as we could and parked just below the town. The way up is steep however they had escalators to take us most of the way. We wandered the steep narrow streets with medieval architecture. From the perimeter of the town, we had an expansive view of the Valdichiana valley. We walked down the main street via Nazionale, the only street with no gradient, and enjoyed looking in the many artisan stores.

Montepulciano

Montepulciano is also a medieval hilltop town but slightly larger than Cortona. It has many impressive historical buildings and a wide selection of quality food/drink stores. Montepulciano is a major producer of food and drink and is known for its cheese, ‘pici’ pasta, lentils, honey, and wine. Montepulciano is surrounded by vineyards and it’s Vino Nobile is considered among Italy’s best. Most of the shops and restaurants are on the main street between Porta Al Prato and Piazza Grande. The best views are from a tower in the 14th-century Palazzo Comunale.

We hope this blog helped you with your planning. If you have any questions, don't be afraid to ask!

Fun In The Tuscan Sun - Countryside