italy
Tuscany
Rolling Hills & Wine
Cypress-lined roads wind through golden hills dotted with medieval villages. This is the Italy of your imagination—where wine cellars hold centuries of tradition, Renaissance art hangs in parish churches, and every meal becomes a celebration of simple perfection.
Best Time
April to October, with harvest season (September-October) particularly magical
Duration
5-7 nights recommended
Ideal For
Wine Enthusiasts, Couples, Culinary Travelers, Art Lovers
The Stay
Historic estates transformed into intimate retreats where vineyards meet luxury.
Rosewood Castiglion del Bosco
A 5,000-acre Brunello estate with restored suites in an 800-year-old borgo.
- Private cooking school
- Estate winery
- Championship golf
Castello di Casole
A 10th-century castle surrounded by 4,200 acres of pastoral perfection.
- Villa accommodations
- Working farm
- Spa in ancient cellars
Borgo San Felice
A medieval hamlet reborn as a Relais & Châteaux property.
- Chianti vineyards
- Michelin dining
- Village atmosphere
The Palate
From Brunello to bistecca, Tuscany is where Italian gastronomy reaches its purest expression.
- Truffle hunting with trained dogs in the San Giovanni d'Asso forests
- Private Brunello vertical tastings in historic Montalcino cellars
- Pasta-making with a nonna in her farmhouse kitchen
- Olive harvest participation with mill pressing
The Stillness
Moments when the beauty of the land renders you speechless.
- Watching sunrise paint the Val d'Orcia gold from a hilltop chapel
- Evening passeggiata through San Gimignano's medieval towers
- Floating in a heated infinity pool overlooking endless vineyards
Begin Your Journey
Ready to explore Tuscany?
Let us craft a bespoke journey tailored to your interests.