Ah, Tuscany. With its medieval towns and hilltop fortresses, rolling vine-planted hillsides and olive groves, art-rich cities and fashion powerhouses, Tuscany truly is Italy’s most magical province.

And you are headed there! Your home for the week is at the Jackson Family’s glorious Tenuta di Arceno estate. Located in the province of Siena, known as the medieval Gothic jewel of Tuscany, the estate is bordered by the ancient walled town of San Gusmè and traces its history all the way back to pre-Roman times. You will spend the week enjoying a curated collection of winery experiences, lunches, and dinners.

The main attraction will be Il Palio di Siena, the famed (and spectacularly thrilling) horse race that has been attracting visitors to Siena since the 1500s. You’ll have a first-class view from a private apartment overlooking the Piazza del Campo, one of Europe’s great medieval squares. Accompanied by an Italian feast, you can cheer on your adopted Contrada’s horse and jockey from your private perch. Your insider access to this exhilarating spectacle also includes what many consider the ultimate prize: attending a traditional Contrada dinner the night before the big race.

Designed for 2 couples. Travel dates are August 10 – 17, 2022.