Day 1: Welcome to Tuscany

Make your way to the hilltop gem of San Gimignano, famous for its medieval towers, winding cobblestone streets, and breathtaking countryside views, where your accommodation is set right within the historic walls.

Day 2: Chianti Wine Country & San Gimignano

Set out on a scenic adventure through the rolling Chianti hills, where storybook vineyards, cypress-lined roads, and medieval hamlets capture the essence of Tuscany. Your local guide will share insights into the region’s wine traditions and hidden gems as you visit three exceptional wineries.

At the first estate, meet passionate vintners and taste a curated selection of wines like Chianti Classico, Vernaccia, and robust Super Tuscans, paired with aged balsamic vinegar and truffle-infused olive oil.

Continue to a second winery for an immersive vineyard and cellar tour, where you’ll uncover the art of winemaking passed down through generations.

At the final stop, enjoy an intimate tasting experience surrounded by the Tuscan countryside. Compare vintages, discover new blends, and toast to an unforgettable day among the vines.

Spend the rest of the afternoon at your leisure. Enjoy dinner at a cozy trattoria, take a sunset walk through San Gimignano, or hop on a quick bus to Siena for a spontaneous evening visit.

Day 3: Relax & Check Out

Wake up to another serene morning in Chianti, feeling refreshed and fully immersed in the Tuscan rhythm. After breakfast, check out of your accommodation, but the experience doesn’t have to end just yet.

Choose from a variety of relaxing or active add-ons to make your weekend last a little longer, perhaps a cooking class on a local farm, a horseback ride through the vineyards, or a rejuvenating spa morning complete with heated pools, sauna, Turkish bath, and herbal tea lounge.