Il Borgo

In Montalcino, relax by the pool at Castello Banfi’s 14-room hotel in a 19th-century building restored to gorgeous effect by American Cristina Mariani-May, a co-CEO of the family winery. Enjoy the view from this hilltop hamlet nestled in Tuscany's winery-filled Brunello region. The hotel offers weekend culinary classes taught by chef Heinz Beck, from Rome's Michelin three-starred La Pergola restaurant. Book the Federico Forquet-designed Double and Classic rooms - they're a generous 432 and 540 square feet, respectively.