Is there anything more idyllic than a week spent driving through the rolling hills of Tuscany, sipping Chianti & Brunello while savouring hearty Tuscan fare before retreating back to your rustic countryside villa? We think not.

The thought of summer holidays in Italy conjures many images of Venetian gondola rides, savouring gelato in the streets of Rome and gazing out from the cliffside restaurants in the Amalfi coast. Each Italian city and region possesses it’s own charm, but it often comes with a crowd to match. This summer, step off the beaten path and take in the Tuscan countryside - read on for my recommendations of where to stay and where to visit.

TO STAY: Borgo Pignano

Borgo Pignano is a true Tuscan paradise. Located near Volterra, the property spans 750 acres of organic farmland and sustainability is woven throughout every facet of the infrastructure and offerings. Accommodation includes spacious rooms and suites in the main hilltop villa, as well as several private villas and ‘maisonettes’ for families and larger groups who prefer a bit more privacy. Activities available include everything from horseback riding, wine tasting, cooking and yoga classes, but you could easily spend the entire afternoon relaxing by the cliffside infinity pool carved from an ancient limestone quarry and sipping cocktails from the pool bar.

Rooms are spacious and decorated in true Tuscan style, featuring organic Lavender bath products produced with the property’s homegrown herbs, as well as a welcome bottle of Borgo Pignano’s own Rosso del Guardia wine.

Breakfast is included in the rate and features a delicious spread of Italian charcuterie and pastries (including fresh honey from Borgo Pignano’s own bee farm), alongside an à-la-carte menu of omelettes and other typical breakfast dishes.

For lunch and dinner, Villa Pignano, the more upscale of the two restaurants on property, has both beautiful indoor and outdoor seating and a rotating seasonal menu. Ask for the outdoor corner table overlooking the infinity pool which boasts a perfect sunset view. Restaurant Al Fresco, a more casual option on-site, serves up delicious wood-fired pizzas, pastas and other hearty Italian fare. Before dining at either restaurant, make sure to enjoy a pre-dinner cocktail outside in the main courtyard during golden hour.

Don’t forget to visit their shop on-property to take home some of their organic olive oil, lavender essential oil and other bath products, wine or even fresh honey from their bee farm.

TO STAY: Villa di Piazzano

The Villa di Piazzano, a member of the Small Luxury Hotels of the World group, is a slice of true Tuscan history. Build in the early 1500s by Cardinal Silvia Passerini, it is now classified as a historical residence. Located on the Tuscany-Umbria border and a short 10 minute drive outside of Cortona, the property is the perfect base to explore both regions or to simply relax by the pool. All rooms feature beautiful, polished decor and the service was outstanding.

L'Antica Casina di Caccia is the property’s fine dining restaurant, including a cozy indoor dining room for cooler spring and fall months and a beautiful al fresco service during the summer. Breakfast is served outdoors and includes a generous spread of charcuterie amongst à la carte options.

TO STAY: Villa Bordoni

This family-owned property in the Chianti region - a mere 1-hour drive from Florence - overlooks the Tuscan hills and the small town of Greve. This 16th-century restored villa holds less than a dozen rooms, each of which are uniquely outfitted in traditional Tuscan-countryside fashion, and has a warmth that makes it feel like it’s your own home.

Enjoy breakfast in the garden each morning before heading out for local winery tours or touring the area, returning for a relaxing afternoon by the pool. For dinner, you don’t need to look any further than their own in-house restaurant which has a rotating menu of local Tuscan dishes to be savoured. Worth noting is the villa’s cooking class, where you can spend the late afternoon learning to make fresh pasta, eggplant parmesan and tiramisu, all while savouring local wines from the property’s vineyard. Let the in-house chefs complete the cooking and serve you the fruits of your own labor for dinner under the evening sky - buon appetito!

TO VISIT: Antinori nel Chianti Classico Winery

Ranked #1 in the 2022 World’s Best Vineyards Awards, and not surprisingly. Antinori nel Chianti Classico is located about 1-hour outside of Florence by car, and is something of a modern architectural marvel in the wine world, particularly amongst the typical country charm of many other vineyards in the region.

Book the CRU tour, which provides an in-depth look at the history and legacy of the Antinori family, a complete tour of the vineyards and production facilities and a wine tasting of various vintages in the suspended glass room overlooking the aging barrels. The tour is followed by a sun-soaked lunch at Rinuccio 1180, complete with views of the vineyards, an incredible 3-course lunch and wine pairings. If you only have time for one wine tour, make it this one.

TO VISIT: Castiglion del Bosco Winery

Restored in 2003 by the Ferragamo family, this winery is part of the Rosewood Castiglion del Bosco property and is one of the best Brunello di Montalcino producers in Italy. Book a private tour for an exceptional experience learning about Brunello production, touring the ‘Millecento’ cellars and enjoy a tasting across several vintages.

TO VISIT: Fattoria Viticcio Winery

Located near to Villa Bordoni, Viticcio specializes in Chianti Classico and is the perfect vineyard for a quick tour and tasting in the area. Make sure to visit their shop and take home a few bottles as gifts (or for yourself!)

Under the Tuscan Sun