Natalie with guests and glasses in hand

Retreat · ran 15-22 August 2026

Tuscany Retreat August 2026

A week of slow living in Tuscany, discovering family-run wineries, lingering over long lunches, and soaking up the charm of its beautiful hilltop towns.

The week

A week well spent in Tuscany

August 15-22

Day by day

Day one

Arrival and a first table

Arrive at our private, family-owned hilltop retreat overlooking Lake Trasimeno. Unwind, take in the breathtaking views, and settle into the Tuscan countryside before gathering for a beautiful farm-to-table dinner at the property.

Day two

Cortona & Olive Oil Tasting

Discover the art of olive oil making at a family-owned mill, followed by a peaceful walk through a historic Franciscan forest. Explore Cortona’s charming streets before enjoying a traditional three-course lunch with truffle pasta and local wine.

Day three

Siena and Chianti

Discover Siena’s rich history with a visit to one of its historic districts and the magnificent Siena Cathedral, followed by a stroll through its medieval streets. Journey into Chianti to visit a pioneering natural wine vineyard, learn about its winemaking philosophy, and enjoy a guided tasting paired with lunch.

Day Four

Relaxed Tuscan Living

Enjoy a relaxed day by the pool, soaking up the Tuscan sun. In the evening, savour a lakeside sunset aperitivo before heading to Perugia for dinner and an evening exploring its charming historic streets.

Day five

Val d’Orcia: Cheese, Wine & Tuscan Charm

Discover the rolling hills of Val d’Orcia, explore the Renaissance town of Pienza, and savour local pecorino at an artisan cheese producer. Enjoy a wine tasting in a historic family-run cellar overlooking the valley before wandering through Montepulciano’s charming streets and boutiques.

Day six

Wine, Pool & Indulgence

Enjoy a relaxed final day with a wine tasting and lunch at the relais, time by the pool overlooking Lake Trasimeno, or an indulgent massage at a nearby vineyard. Unwind and savour Tuscany at your own pace.

Tuscany Retreat August 2026 | Roam with Red