Tuscany: 3-Day San Gimignano & Chianti Wine Tour｜Italy

Day 1 - Welcome to Tuscany
Make your way to San Gimignano, one of Tuscany’s most enchanting hilltop towns. Famous for its striking medieval towers, cobblestone lanes, artisan shops, and sweeping countryside views, this UNESCO-listed destination feels like a journey back in time.

Settle into your accommodation, conveniently located within the historic walls, and begin exploring at your own pace. Wander through picturesque squares, discover quiet corners, and admire the warm colors of the Tuscan landscape. In the evening, choose a traditional trattoria and enjoy the welcoming atmosphere of this remarkable medieval town.

Day 2 - Chianti Wine & San Gimignano
Embark on a scenic journey through the rolling hills of Chianti, where vineyards, olive groves, cypress-lined roads, and ancient villages create the quintessential Tuscan landscape. Along the way, your local guide will introduce you to the region’s history, winemaking traditions, and lesser-known treasures.

Visit three carefully selected wineries, each offering its own character and approach to Tuscan wine. At the first estate, meet passionate local producers and enjoy a curated tasting featuring celebrated wines such as Chianti Classico, Vernaccia, and bold Super Tuscans. Complete the experience with samples of aged balsamic vinegar and aromatic truffle-infused extra virgin olive oil.

Continue to a second winery for an immersive visit through the vineyards and cellars. Learn how the landscape, climate, and generations of expertise shape every bottle while discovering the key stages of the winemaking process.

At the final estate, relax in the peaceful Tuscan countryside during an intimate tasting. Compare different vintages, discover distinctive blends, and raise a glass to a memorable day among the vines.

Return to San Gimignano and enjoy the rest of the afternoon and evening at your leisure. Browse local boutiques, taste traditional specialties, take a sunset walk along the medieval walls, or enjoy dinner in a cozy trattoria. For an additional adventure, you may also take a short bus ride to Siena and experience another of Tuscany’s most beautiful historic cities.

Day 3 - Relax & Check Out
Wake up to a final peaceful morning in the heart of Tuscany. Enjoy breakfast and soak up the relaxed atmosphere before checking out of your accommodation.

If you would like to extend your experience, choose from a selection of optional activities. Learn the secrets of regional cuisine during a hands-on cooking class at a local farmhouse, ride through the vineyards on horseback, or unwind with a rejuvenating spa experience featuring heated pools, a sauna, a Turkish bath, and an herbal tea lounge.

Whether you prefer food, adventure, or complete relaxation, these optional experiences offer the perfect conclusion to an unforgettable Tuscan escape.