Tuscany, Italy

We spent some time driving through the countryside of Tuscany, exploring the various mid-evil hilltop towns, and surrounding villages. With its golden light, long shadows, endless acres of olive groves and vineyards, and beautiful sunsets, here are some of our absolute favorite places.


Known best from the movie, Under the Tuscan Sun, Cortona is truly a magical village. With it’s stone buildings, cobblestone streets, and narrow alleys leading to secluded restaurants decorated with twinkling lights, it was perhaps our favorite of all the Tuscan villages.

Must Dine

  • Trattoria La Grotta. Italian food as it was meant to be made, in a cozy Tuscan restaurant, you’ll enjoy the house Chianti in a traditional clay pitcher, mouth watering, cheese-filled gnocchi, and other dishes such as eggplant with mozzarella and parmesan cheese. Tiramisu for dessert is a must.
  • 500 Bar. This is a historical staple to Cortona where you can find local favorites such as focaccia paninis with Parma ham, tuna salad with fresh corn and olives, pizza and pasta, all complimented by the best of local Tuscan and Umbria wines.

Must imbibe

Apperitivos, known more commonly as aperitifs, are popular across Italy. In Cortona, you can enjoy a spritz (prosecco, Aperol and a splash of club soda), the most commonly preferred apperitivo alongside complementary appetizers that can range from small pieces of bread with cheese and truffle oil, to small slices of pizza with other pastries and treats.

Must stay

Appartamento del Borgo. We rented an authentic Tuscan-styled, terra-cotta apartment, adorned with copper accents and wine cellar arches. We were welcomed by the most adoring host, who gifted us with a bottle of local Tuscan wine, and ensured we had everything we needed before she stepped out. Set atop the hill of Cortona, it offered an ideal location, right in the heart of the old town, steps away from the charming restaurants, shops and galleries. Parking was also convenient. To book, visit the listing on FlipKey.


Another mid-evil city, with a number tasting shops lining the entrance, where you can tour proper centuries-old wine cellars, taste Montepulciano wines, and sample local cheeses.

Must visit – Vineyard

Salcheto Vineyard. Interestingly, this vineyard is the first company in the world to have certified the carbon footprint of a bottle of wine, with solar tubes illuminating the wine cellar, a vertical garden cooling the wine cellar, and a recycled watering system on the roof to cool the cellar as the temperature increase throughout the day. The vineyard is set in the peaceful hills of Montepulciano, with three main types of wine stemming from this region: Vino Nobile, Riserva and Salco. Tours are incredibly thorough, given daily for 10 Euro per person, or are free with the purchase of a bottle.

Must know – Montepulciano Wine

Vino Nobile, Riserva and Salco, the wines from the Montepulciano region, are first aged in barrels almost 3x larger than traditional French Oak. They are then moved to French Oak, and then bottled for final aging before they are labeled to ship.

Colmatores, also known as a cask fillers, monitor the levels and aging process of the wine without risking oxidation. It was interestingly designed by Leonardo di Vinci, as traditional bung holes wouldn’t work with barrels of this size. You’ll see them on top of each barrel.


Known largely from the film, La Vita e Bella (Life is Beautiful), Arezzo is commonly considered the jump off to the rest of Tuscany. Though, if you have some time to spend here, we have some recommendations to fully enjoy your stay.

Must stay

Estate il Palazzo. The countryside in Arrezzo is perfect for a getaway, and to fully enjoy, we’d recommend staying at this beautiful farmhouse tucked away in a wine vineyard. You can relax by their pool, or enjoy a complementary vineyard tour and tasting of their wines. You’ll also be welcomed with a bottle of their wine, which we thought was a nice treat to complement our star gazing. Insider tip: This vineyard supplies the wine for the restaurant Serafina’s house label.

Must dine

  • La Capannaccia. This restaurant is set in the hills of Arrezzo, with a fantastic view through the trees into the valley. Known for their open grilled meats, perfectly seasoned, the food is excellent. Each pasta dish, notably the dishes with wild boar sauce, is delicious. You’ll also receive unlimited amounts of their house wine to complement your dining experience as well.
  • Bistrot 31. Elevated Italian cuisine in the Old Town, consistently rated #1 on TripAdvisor, you’ll be able to taste everything from quinoa with frommage mousse to an elaborately plated poached egg. Tobacco mousse for dessert is an interesting treat, but for a more traditional end to your meal, they do have a decedent chocolate cake as well.
  • Albikokka Restaurant. Found on the outskirts of the Old Town, you’ll walk into this cozy dining room decorated with modern glasses of olive oil and comfortable rose cushioned booth styled seats. We sat down to the waiter pouring us prosecco, on the house, followed by a complementary appetizer of bruschetta fixed with burrata, shrimp and strawberries in a reduction that tasted like a mix of cheese and cream. We had chosen to split a few dishes, and they thoughtfully brought each out on separate plates. The food was outstanding, and the service was well above par. Each course was brought to us by the chef, and he had a smile on his face each time. He even corked and packaged our wine in a proper box to go! Absolutely a recommend and much better than most restaurants in the actual old town of Arrezzo! Insider tip: Make sure to order the Canoli’s Traveling from Sicily as a starter.


Tuscany’s sister, Umbria is lesser known, but just as beautiful, with it’s own set of notable wines. We drove through it one morning to visit a vineyard, but it would be worth spending more time in the area if your plans allow. Insider tip: Most restaurants are closed on Mondays.

Must visit – Vineyard

Castello Monte Vibiano Vecchio S.R.L. This is a family owned, Eco-friendly vineyard with a collection of electric jeeps that you can personally man, to drive through the grape vineyards and olive groves on your tour. The comprehensive tasting takes you through the notes you’ll taste in each wine, how the wines received their names (all are after the members of the family), and pairing recommendations. You’ll also get a chance to sample their estate-made olive oil. Reservations are required, and can be arranged quickly by giving them a call.

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