Tuscany: La Dolce Vita

Your journey kicks off in Florence, where the group gathers to embark on a scenic drive through Tuscany's gentle hills. Along the way, we pass through charming hilltop villages and verdant landscapes en route to our private villa near Asciano, located just 30 kilometers from Siena.

We’ll pause for lunch at Osteria Delle Crete, nestled in the truffle-rich village of San Giovanni d’Asso. Upon arriving at the villa, guests can unwind with a swim in the pool, take time to journal amid the olive groves, or relax while soaking up the sweeping countryside views. The evening will feature a welcome dinner under the stars, paired with regional wines, setting the tone for a restful first night in Tuscany.

After an optional morning yoga session and breakfast, we travel to the storied town of Montepulciano. Perched along a limestone ridge, Montepulciano offers spectacular views over the Val d’Orcia and is famed for its Vino Nobile wines. Our private guide will introduce us to the town’s hidden pathways, offering insight into both its culinary heritage and historic landmarks.

We’ll explore De’Ricci’s renowned wine cellar—often called the “Cathedral of Vino”—with one of its owners, enjoying a private wine tasting. Lunch and a tasting at the vineyard’s secluded estate follow, giving us time to appreciate the full flavors of the region. The day winds down back at the villa with optional sunset yoga and a relaxed dinner prepared by our personal chef.

The morning begins with yoga and a wholesome breakfast before heading to Bagno Vignoni, a tranquil village known for its ancient thermal baths. Nestled in the heart of the Val d’Orcia, this quiet gem has long drawn visitors seeking rejuvenation.

Enjoy a leisurely lunch at a local trattoria, and afterward, explore the village’s stone-paved streets built around a central hot spring. You may choose to hike the scenic trails nearby, indulge in a spa experience, or simply unwind with a glass of wine before returning to the villa for a restful evening.

Following optional yoga and breakfast featuring fresh local produce, we make our way to the hilltop town of Montalcino, world-famous for producing Brunello di Montalcino, one of Italy’s finest wines.

With a knowledgeable local guide, we’ll uncover Montalcino’s lesser-known corners, followed by lunch at an authentic local eatery. The day concludes back at the villa with an exclusive tasting experience. Our friend Gianluca, a passionate restaurateur, will lead the group through a curated selection of Montalcino wines, sharing personal stories that reveal the artistry behind the region’s winemaking traditions.

After yoga and breakfast, we venture to Chiusure, a small town known for its breathtaking views of the Crete Senesi’s distinct clay hills. Here, we’ll enjoy a casual picnic lunch before descending into a serene cypress forest to explore Monte Oliveto Maggiore, a 15th-century Benedictine abbey.

On a private tour, guests will wander through the peaceful cloisters and marvel at the frescoes that depict scenes from the life of Saint Benedict. Upon returning to the villa, the evening culminates in a hands-on cooking class with a Michelin-starred chef, where guests will create a memorable Tuscan meal to share for our final dinner together.

Our final morning offers one more chance to participate in yoga or enjoy the villa’s tranquil setting. Breakfast will feature local specialties, thoughtfully prepared by our chef, offering a delightful farewell to Tuscany. The group will then transfer back to Florence, where we’ll say our goodbyes and head home, enriched by the beauty, food, and culture we’ve experienced.