Castel Monastero RESORT

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.

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.

Nestled by Monticchiello's gate, Osteria La Porta charms with a cozy rustic vibe, delicious traditional cuisine, and stunning views from its terrace.

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

If you've found us you've been digging deep, searching for something different; something unique, hip, exclusive, chic. A place that buzzes via genuine old fashioned word of mouth. A place visited by groovy, choosy people... like you. 200 year old Leopoldina stone villa in tuscany An historic, square, brick and stone villa on a bluff, with long, long views. Dating from around 1750, abandoned since the 1940's, a beautiful plundered ruin transformed into a blissful hideaway by it's English owners. Restored to forever-house specifications, with a sculptor's eye and a design-loving purse, the spirit and layout of the property stay true to it's Tuscan country house heart. Only 4 luxurious bedrooms. So much space. Large open retreat and socializing zones within on both floors. Outside: Walled Tuscan country garden. Nature. Soft lawns to pad about on. Large salt water pool with breezes and views. Comfort and escape whatever the weather. Located well for sight seeing we are recommended for Tuscany explorers, designer shoppers, wine tasters, hill town climbers, chic city window-shoppers, Florence day trippers, romantic weekend away stay-at-homers, and easy connections for Rome. If you can't decide which gorgeous Tuscan hill town or valley to base yourselves in then this might also be the spot for you. WORD OF MOUTH: From the Experts. MONOCLE: 'The couple's deep knowledge of the area teamed with their fine cooking skills make for the perfect rural Italian holiday' ~ Daniel fisher.

La Prosciutteria is a cozy gem in Siena, where you can savor Tuscan meats and fine wines, all while enjoying the charming ambiance and friendly vibe.

Villa Pianigiani is a beautifully restored 18th-century gem in Chianti, merging historical charm with exquisite Tuscan cuisine and fine wines.

Nestled in the heart of Tuscany, Fonterutoli is a charming village near Castellina in Chianti, offering a quaint escape with only 80 residents.

Nestled in a luxurious 10th-century castle, this enchanting Tuscan hotel boasts exquisite dining, a lush pool, and attentive service amid stunning vineyards.