Discover the charms of the Tuscan countryside as you explore the stunning medieval towns of Siena and San Gimignano. Take in the breathtaking sunset setting over rolling hills as you settle down to a 3-course dinner and wine in a traditional Chianti winery.

Journey by comfortable minivan through the lush country roads to Siena, the only town that competed with Florence in terms of Renaissance significance. Stroll through the delightful streets and into Piazza del Campo, the main central square, where the famous Palio horse race takes place each year. Venture into the quaint backstreets and listen as your guide explains the history of the contrades, the 17 medieval city districts that compete against each other in the Palio.

Continue to a picture-perfect example of a Tuscan hill town, San Gimignano. Marvel at the remarkably intact medieval “skyscrapers” that have miraculously survived war and natural elements for centuries. Enjoy some free time to wander through the twisting streets and shop for traditional souvenirs in the small boutiques.

Soak up the splendid sunset views and then sit down to enjoy an authentic Tuscan dinner in a beautiful location in the Chianti countryside. Relax in the surroundings with the delicious wine before making your way back to Florence at the end of the evening.