Hotel Certosa Di Maggiano  

Tucked into Tuscany’s rolling hills just outside Siena, this boutique hotel sits in a restored 14th-century Carthusian monastery. It’s a short drive into Siena’s medieval center—think Piazza del Campo, Porta Romana and Torre del Mangia—and it backs onto a nearby golf course. Family-friendly and pet-friendly, perfect for countryside escapes with city access.

Light-filled rooms and historic interiors were sensitively reworked by a noted architect, with silks, ornamental paintings and a calm, elegant vibe. Rooms are individually decorated and come with Select Comfort beds and Frette-style linens, minibars (and some espresso makers), plus private baths with deep soaking tubs and bidets.

Soak in an outdoor pool, hit the outdoor tennis court, or borrow a bike to roll through olive groves. There’s a spa and massage room, poolside bar and a library plus picnic and barbecue areas. Concierge service, babysitting (surcharge), free self-parking, limo/town-car service and both wired and wireless internet keep things easy; airport shuttle available for a surcharge.

A conference hall and meeting spaces are on-site, and complimentary high-speed wired internet makes remote work straightforward.

An on-site restaurant focuses on regional Tuscan flavors and a sensory-driven dining experience, with a coffee shop/café for snacks and a poolside bar for evening drinks. Room service is available during limited hours and a complimentary buffet breakfast is served each morning (typically around 7–10:30).