Tuscany is a world-renowned region in central Italy steeped with history and culture. Stretching from the Apennine Mountains to the Tyrrhenian Sea and encompassing the enchanting towns of Siena, Arezzo, Pisa, Montepulciano and of course Florence (the region’s capital), Tuscany is celebrated for its abundance of Renaissance art and architecture, medieval villages, stunning countryside, sprawling vineyards and olive groves.

During a recent scouting trip, KKTWW had the opportunity to experience Tuscany’s old-world charm and visit some of its top destinations and luxury properties.

Belmond Castello di Casole

• Vibe: Luxurious, old-world Italian
• Accommodations: 39 rooms and suites
• Amenities: 3 restaurants, bar, outdoor pool, wildlife safaris, truffle hunting, vineyards, olive groves, cooking classes, pizza-making classes, biking, fitness center, personal training, yoga, Pilates, spa with multiple treatment rooms, pools and steam rooms
• Good For: Couples and families

Borgo Pignano

• Vibe: Charming, historic country estate
• Accommodations: 14 rooms and suites in the main 18th-century villa, 2 historic suites located in the Priest’s House, 8 maisonettes, 2 cottages and a large country farmhouse that sleeps up to 20 people
• Amenities: 2 restaurants, 3 swimming pools (including 1 children’s pool), hiking, biking, and horseback riding on the extensive path network, farm tours, wine tasting, cooking classes, art classes, herbal laboratory, yoga, spa, fitness room
• Good For: Families and couples

Borgo San Felice

• Vibe: Classic, rustic, authentic luxury
• Accommodations: 60 rooms and suites located throughout various structures within the ancient Tuscan village and 2 villas
• Amenities: 2 restaurants, bar, outdoor pool, gym with sauna and Turkish bath, tennis courts, spa, bio-sauna, vineyards, wine cellar, olive groves, bocce court, cooking classes, wine tasting, e-bike tours, yoga, Pilates, personal trainer
• Good For: Couples and families

COMO Castello del Nero

• Vibe: Serene, 12th-century castle with contemporary design
• Accommodations: 50 rooms and suites
• Amenities: 3 restaurants including a Michelin-starred option and al fresco dining throughout the summer, bar, wine cellar, outdoor pool (open during summer), 740-acre estate with vineyards and olive groves, truffle hunting, wine tasting, olive oil tasting, honey tasting, stargazing, cooking classes, gelato classes, cocktail-making classes, COMO Shambhala Retreat (wellness sanctuary offering a range of therapeutic experiences including sauna, aromatic steam room, ice fountain, heated vitality pool, meditation sessions, gym, yoga and Pilates classes), tennis courts, complimentary shuttle service to Florence and Siena
• Good For: Couples, families, wellness seekers

Il Borro Estate

• Vibe: Rustic, historic, luxurious
• Accommodations: 38 rooms and suites spread throughout the medieval village, 18 rooms and suites in Aie del Borro’s verdant countryside setting, 5 charming farmhouses and 3 luxurious villas ranging in size from 2 to 10 bedrooms
• Amenities: 2 restaurants, bar, Wines & Art Gallery, wine cellar, golf, horseback riding, yoga, tennis courts, trekking paths, football pitch, mountain biking, truffle hunting, cooking classes, wine tasting, local artisan workshops
• Good For: Couples and families who don’t mind walking through the property’s curving cobblestone streets or using the shuttle service

Relais Borgo Santo Pietro

• Vibe: Romantic, luxurious, intimate
• Accommodations: 20 individually styled rooms and suites
• Amenities: 3 restaurants, bar, wine cellar, spa featuring indoor and outdoor treatment suites, 13 acres of beautifully manicured gardens, 270-acre organically cultivated farm, vineyards, cooking school, cheesemaking, wine tasting, art lessons, floristry, estate and garden tours, beekeeping, falconry, archery, bocce court, tennis courts
• Good For: Adults and honeymooners

Rosewood Castiglion del Bosco

• Vibe: Palatial, chic, historic estate, amenity-rich
• Accommodations: 23 suites within the historical buildings of the Borgo and 11 expansive 3- to 6-bedroom villas, which feature heated pools, terraces and gardens overlooking the countryside
• Amenities: 2 restaurants, 2 bars, outdoor pool, spa with sauna and steam bath, fitness center, yoga, Pilates, personal trainer, private winery, cooking school, wine tasting, golf, tennis, truffle hunting, nature walks, hiking, mountain biking, bocce ball, archery, photography courses, painting courses, astronomy courses, falconry, kid’s club
• Good For: Couples and families