Castel Monastero RESORT

Tucked away in restored 8th-century buildings, this luxe Tuscan hotel boasts inviting rooms, two stellar restaurants, a serene spa, and a picturesque pool amid vineyards.

Polished quarters on a venerable estate with a high-end restaurant, a chic spa & 2 outdoor pools. Overlooking vineyards and olive groves on a rural estate, this elegant hotel is 15 km from both Duomo di Siena, an imposing 13th-century cathedral, and Piazza del Campo, home of the legendary Palio di Siena horse race. Refined rooms come with minibars, flat-screen TVs and free Wi-Fi; some have country or garden views. Suites add living rooms with pull-out sofas, while a separate stone-built villa offers a private garden. The hotel features an upscale restaurant with exposed-brick hints, and a spa with an indoor pool and grape-based treatments. There are also 2 outdoor pools, along with an 18th-century garden, tennis courts and a fitness room.

Refined hotel in a 13th-century hilltop property with upscale dining & 2 pools, plus a gym. Set in the Chianti region, surrounded by vineyards, this upscale, hilltop hotel in a restored 13th-century building is 21 km from Siena and Piazza del Campo square. Featuring terracotta floors and beamed ceilings, the rustic rooms and suites have free Wi-Fi, flat-screen TVs and desks. Upgraded rooms and suites add separate living areas, terraces and/or private gardens. Room service is available. Freebies consist of a breakfast buffet, an area shuttle, parking and bike rentals. There's also an elegant restaurant with panoramic terrace views, plus a bar, a snack bar, and indoor and outdoor pools. Other amenities include a gym and a sauna.

Nestled in the stunning Val d’Orcia hills, this luxurious seasonal hotel boasts lavish suites, a serene infinity pool, and impeccable service—your dream Tuscan getaway.

Nestled in stunning Tuscany, this restaurant serves up unforgettable views alongside a menu featuring unique twists on traditional dishes, all underscored by friendly, attentive service.

In the heart of Montepulciano, this elegant family-run hotel in a former seminary offers stunning views, cozy rooms, and a delightful breakfast experience.

Tucked away in the Tuscan hills, this chic adults-only B&B boasts stunning vineyard views, an idyllic pool, and a Michelin-starred restaurant for a perfect getaway.

Nestled within ancient walls, this upscale hotel offers cozy rooms, a lovely Tuscan restaurant, and a charming terrace with views of the countryside, all just a short stroll from Siena's highlights.

A cozy family-run spot serving up hearty Tuscan favorites like pici pasta and white bean soup, with a lively deli counter vibe.

Nestled near Piazza del Campo, Gallo Nero serves upscale Italian fare in a stunning vaulted brick space, pairing exquisite dishes with a stellar wine selection.