Tuscany, Italy
With its beautiful rolling hills and Mediterranean cypress trees, spectacular medieval-walled towns, and world-renowned food and wine, Tuscany has so much to offer.
Dream
La Bandita Countryhouse: Home base for our trip was La Bandita Countryhouse, just outside the small town of Pienza in the Val d’Orcia region. The town lies between Montalcino and Montepulciano.
Our stay at La Bandita was absolutely amazing — a true gem nestled in the Tuscan countryside, blending charm, comfort, and impeccable style. Unfortunately, the property has since closed, although the owner also runs a boutique hotel in Pienza called La Bandita Townhouse. If the hotel offers anything like the experience of the country house, it’s sure to be extraordinary — anything less would be a surprise.
On our second trip to Tuscany, inspired by our stay in the country house, we rented a home for a group of four couples and discovered an amazing property called Tramonti in Castellina di Chianti. This exquisite villa perfectly captures the essence of luxurious Tuscan living, set amidst the rolling hills of Chianti. Spacious and beautifully appointed, the home offered stunning comfort and privacy. With an exceptional house manager and private chef taking care of every detail, our stay was effortless and so enjoyable that we truly didn’t want to leave. Renting a home like Tramonti through a company such as Red Savannah provides personalized service and unmatched relaxation—a perfect way to celebrate a big occasion or simply savor an unforgettable escape in Tuscany.
Dine
In addition to memorable dinners at home—featuring homecooked meals with wine and personalized menus—here are a few restaurants we experienced during our stays in Tuscany.
La Cantinetta di Rignana(near Castellina in Chianti): A bit of a journey to reach, but absolutely worth every minute. Nestled in the scenic Tuscan countryside, this charming restaurant offers stunning panoramic views that perfectly complement its exceptional cuisine. Guests are treated to authentic, thoughtfully prepared dishes that celebrate local flavors and ingredients, making every meal here a memorable experience. A true hidden gem for those willing to venture off the beaten path.
Osteria Le Logge (Siena): Traditional white-tablecloth osteria serving very good homemade pastas and fresh local meats and vegetables in the center of Siena, close to the Town Square.
Solociccia (Panzano): Located in the charming Tuscan town of Panzano, this lively restaurant is run by the legendary butcher Dario Cecchini. Known for expertly crafted Tuscan meat dishes, Solociccia offers a warm atmosphere where meat lovers can indulge in some of the region’s best fare. Dario’s butcher shop—famous worldwide and visited by Anthony Bourdain—is just steps away, and his street food cart is perfect for a casual taste of his renowned offerings.
Ristorante Caffè Poliziano (Montepulciano): This classic Tuscan restaurant offers refined regional cuisine with a focus on local ingredients and traditional flavors. Its inviting atmosphere and thoughtful wine list make it a perfect spot to savor the best of the Val d’Orcia. Adding to the experience, the restaurant boasts stunning views over the rolling Tuscan hills and vineyards, making every meal memorable both for the palate and the panorama.
Il Re Gallo (Castellina in Chianti): This Osteria offers a cozy and rustic atmosphere that reflects the charm of Tuscany. Established in 1999 by Andrea, the restaurant is renowned for its creative take on traditional Tuscan cuisine, featuring dishes like wild boar, fresh pasta, and seasonal specialties such as truffles and mushrooms . Guests can enjoy a warm and welcoming environment, with many noting the friendly staff and authentic flavors .
Do
Day Visit to Siena: Siena is one of the most visited tourist attractions in the country. It’s most known for its fan-shaped town square, distinctive cathedral, and the Palio – a biannual horse race often featured on television and in movies such as the James Bond film Quantum of Solace.
Siena, which was declared a UNESCO World Heritage Site in 1995, is many people’s favorite town in Tuscany, and it is easy to see why. The Duomo di Siena is a strikingly beautiful 13th-century Romanesque-Gothic building constructed in white and black marble in alternating stripes.
The town square, Piazza del Campo, is formed from herringbone pattern terra cotta tiles, and is a very popular gathering place. The square is dominated by the Palazzo Publico, or town hall, which serves as the seat of Siena’s government. Its campanile or bell tower, Torre del Mangia, was built between 1325 and 1344 and was the tallest structure in Italy at the time. Piazza del Campo is the site of the Palio, the world-famous horse race which is held every year in July and August. Ten jockeys riding horses bareback circle three laps of the square on a thick layer of earth laid specially for the event, which lasts approximately 90 seconds.
Private Wine Tour at Castle of Tignano With Chef’s Lunch: Explore the ancient Castle of Tignano on a private wine tour led by oenologist Riccardo Casamonti. At his boutique winery, Riccardo passionately champions native Tuscan grape varieties, providing an intimate and educational experience. The day’s highlight is a homemade lunch prepared by an exceptional chef in Riccardo’s own kitchen—featuring authentic Tuscan dishes crafted from the freshest local ingredients. This unique blend of wine, history, and heartfelt hospitality creates a truly unforgettable Tuscan experience.
Wine tasting in the Montalcino Region: The vineyards surrounding the town of Montalcino are famed for their Brunello; a red DOCG wine produced from 100% Sangiovese grapes. We hired a driver for a day of wine tasting. After a brief stop at the Medieval town of Montalcino, we visited two local vineyards: Tenuta Fanti and Santa Giulia.
Tenuta Fanti (Montalcino): This was the larger of the two wineries we visited. We took a tour of the winery and the cellars, followed by a tasting of their fine Brunellos.
Santa Giulia (Montalcino): This was a much smaller, family run vineyard. The owner took us on a tour, and we met his father and son along the way. Then we sat down in a rustic stone building for a delightful home-cooked lunch with pasta made to a family recipe that the owner’s wife helped prepare. And more Brunello.
Images from Tuscany
