Explore the heart of beautiful Tuscany on a full-day tour of the towns of San Gimignano and Siena, then discover the bucolic wine region of Chianti. Depart from Florence by an air-conditioned bus to your first stop, the UNESCO World Heritage Site of San Gimignano. Discover one of the most splendid examples of an Italian medieval town. Distinguished by its famous towering skyline, San Gimignano stands along the Via Francigena on the hills of the Upper Val D’Elsa. Get acquainted with the Tuscan environment with the town’s Vernaccia di San Gimignano wine, saffron, and Santa Fina pottery. Enjoy some free time to stroll through the town on your own and see its beautiful squares, architecture, churches, and side streets. Afterward, head out to a unique location in the Chianti countryside to enjoy a wine tasting. Once you hop off the bus, be guided around a splendid winery. Get introduced to the estate's fascinating history and background. Head inside the cellars to learn the secrets of Chianti winemaking together with the local host. Then enjoy a delicious wine tasting of Chianti Classico. Continue to Siena for a guided tour of its enchanting architectural styles, including the Cathedral (exterior only) and Palazzo Comunale (Municipal Building, exterior only) in Piazza del Campo. The famous shell-shaped square provides the stage for the thrilling Palio horse race, run twice every summer.

Spend a day exploring the Tuscan countryside on a chauffeur-driven tour. Immerse yourself in Tuscan culture as you visit Siena's main attractions, explore an ancient hilltop town and discover one of Italy's most beloved wine regions. Your day begins with a hotel pickup to take you to the first stop on your sightseeing excursion, Siena. This historical city is a UNESCO World Heritage Site and famous for its Palio, the bareback horse race that takes around its main piazza. Visit the three must-see attractions in Siena, the Piazza del Campo, Palazzo Pubblico, and the iconic Cathedral, one of the few examples of Italian Gothic architecture. Head back to your car and continue your tour of Tuscany with a drive to the walled hilltop town of San Gimignano. Dubbed the Town of Fine Towers, San is renowned for preserving more than a dozen medieval towers. Wander through this ancient city, explore the alleys and see the Piazza del Duomo and the seven towers that surround this town square. End your day of sightseeing with a visit to the Chianti wine region. Marvel at the unforgettable landscapes with its rolling hills, vineyards, and olive groves.

Explore three of the most ancient and emblematic castles in the heart of Chianti Classico, which also serve as wineries. Visit beautiful estates erected centuries ago and taste a wide variety of prestigious wines. Feast on a gourmet lunch fit for a king as part of this tasting adventure. Enjoy an experience of traveling back in time to three Tuscan castles. Visit one of the best-known and most admired wineries in the region and worldwide. You'll also experience a winery which operates inside the walls of a medieval fortified village, as well as a third picturesque vineyard and castle.