Siena sits on the horizon, but this 14th-century Carthusian monastery on the city's edge is hard to leave. The boutique hotel has 22 very individual rooms: former monks' quarters reimagined with bold headboards, jewel tones, and tiled bathrooms. The gardens are the heart of the place, soundtracked by birdsong. Wisteria for breakfast, wine under the magnolias, afternoons by the pool or on the tennis court.

Once a beautiful boarding school, now one of Florence’s sharpest new stays – this hilltop villa has had a serious takeover. It’s the first Italian outpost from Californian brand Auberge, and it’s a stunner: soft, neutral interiors, curated antiques, and some of the best bathtub views we’ve seen in a while. Despite having 83 rooms, it feels private, peaceful – just birdsong and Renaissance-scenes over Firenze’s terracotta skyline. The city’s buzz is a quick shuttle away, but we’d hang poolside under the olive trees with a spritz in hand. The food scene’s strong (buffet breakfasts, olive oil sommeliers, a glass-walled garden room), and the spa taps into local Tuscan traditions. They’re also big on insider access: private gallery visits, perfumery tours, and butchery classes with local experts.