Accommodations in Gaiole in Chianti near Castello di Brolio (Gaiole in Chianti, Italy)

Gourmet dining with 500+ wine selection, Luxurious Frette Italian bed linens

Michelin-starred Tuscan dining, Infinity pool with panoramic Chianti views

Authentic medieval castle stay, Pool in former castle moat

Historic 11th-century castle stay, Charming on-site regional restaurant

Memorable Dining at On-Site Restaurant, Cycling adventures in Chianti

Relaxing spa and wellness offerings, Authentic Tuscan culinary journey

Multiple pools with scenic backdrops, Michelin-starred fine dining

Vineyard-view outdoor swimming pool, Proximity to Siena and historic towns

On-site restaurant with local Tuscan cuisine, Peaceful countryside location near Siena

Panoramic pool with vineyard views, Traditional Tuscan dining experience

Private villa accommodations, Estate-produced wines and olive oil

Historic 13th-century castle setting, Outdoor pool with hydromassage

Traditional Tuscan dining, Green park views

Indoor/outdoor heated pool, Authentic Tuscan dining experience

Outdoor pool with scenic views, Michelin Guide recognized restaurant

Heated outdoor pool in floral garden, Individually designed elegant rooms

Central Radda in Chianti location, Tuscan dining at La Perla del Palazzo

Outdoor pool with countryside vistas, Authentic Tuscan dining experience

Terrace with city panorama, Elegant reading and music rooms

Terrace with scenic views, Pet-friendly accommodations

Charming Tuscan-style farm stay, Relaxing outdoor pool

Traditional Tuscan dining with garden views, Arranged cultural and culinary activities

Authentic Sienese and Tuscan dining, Elegant lobby with contemporary design

Infinity pool overlooking vineyards, Authentic Tuscan farm-to-table dining

Terrace with city street views, Historic 16th-century building

On-site traditional Tuscan restaurant, Panoramic vineyard pools

Historic residence with art nouveau frescoes, Charming garden and wine bar

Historic 13th-century building, Sweet Italian breakfast

Proximity to Chianti's attractions, Charming, character-filled accommodations

Refined dining with local Tuscan flavors, Multiple thermal pools with unique properties

Panoramic countryside and city views, Historic 14th-century convent setting

Panoramic Tuscan countryside views, Spectacular panoramic swimming pool

On-site Italian restaurant, Restored granary apartments

Rustic charm with traditional design, Expansive garden with panoramic views