Tuscany

Tuscany, Italy's heartland of art, history, and gastronomy, seduces with its rolling hills, vineyard-covered landscapes, and timeless Renaissance cities. Celebrities and connoisseurs are drawn to its world-class wines, exquisite cuisine, and picturesque countryside dotted with medieval towns. Tuscany offers a sublime blend of natural beauty and cultural richness, inviting travelers to immerse themselves in the essence of Italian dolce vita amidst its serene and inspiring settings.

Villa San Valentino

Celebrities that have stayed here
Average price per night

$125

USD

A garden sets the tone at Villa San Valentino, an unfussy retreat in Tuscany. From here, the wider experience of Tuscany remains close at hand.

Castiglion del Bosco, A Rosewood Hotel

Celebrities that have stayed here

Italy

Tuscany

★★★★★ Rating 9.7

Rosewood Castiglion del Bosco turns a centuries-old Tuscan estate into a polished country retreat, pairing medieval stone, cypress-lined hills and Brunello country with suites, villas and a serene pool. Its celebrity story is celebratory rather than speculative: Kate Upton and Justin Verlander held their November 2017 wedding weekend here. Vogue's first-person account quotes Upton naming the resort and describes events across the property; El País independently reported the couple's post-ceremony celebration at the same Rosewood estate.

Il Pellicano

Celebrities that have stayed here

Italy

Tuscany

★★★★★

Il Pellicano cascades through Tuscan gardens to a private rocky cove, preserving the effortless glamour of la dolce vita. Jessica Alba and Danny Ramirez stayed here during their July 2026 Italian escape, pairing boat days and long seaside meals with the beautifully secluded rhythm that made this hotel an icon.