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.

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.

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.

Step into this former hospital turned museum, where 1400s frescoes mingle with Renaissance art and a trove of history waits to be uncovered.

Dating back to 1563, this charming brick fort boasts lush trails, dazzling city views, and an amphitheater, perfect for tranquil escapes or photo ops.

Nestled in a stunning 14th-century palace, this charming inn boasts breathtaking views, elegantly decorated rooms, and a vibrant wine bar with live jazz.

Nestled in Tuscany, Monteriggioni enchants with its medieval charm, picturesque fortifications, and stunning views over the lush Chianti countryside.

Nestled near Piazza del Campo, TeKeVoi serves up delicious street food like burgers, focaccias, and pastas in a cozy spot perfect for a quick bite.

An extraordinary culinary gem just outside Siena's city walls, where exceptional service meets a unique dining experience with delicious, thoughtfully crafted dishes.

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.