After a 90-minute drive from the port of Livorno, about half of it spent winding through the Tuscan countryside, we’ll arrive in San Gimignano. Its nickname “The Manhattan of Tuscany” paints an immediate picture, but in this case, we have Medieval towers instead of modern skyscrapers. When you walk through San Gimignano, you might very well feel you are in a fairy tale. You will surely feel you have stepped back in time. Its towers were constructed by nobles between the 11th and 13th Centuries, and the village yet feels of that era. San Gimignano is also historically significant because of its position on the Via Francigena, the pilgrimage route between Canterbury, England and Rome that was so important during Medieval times. Today, San Gimignano is a bustling tourist destination, loaded with chic boutiques and award-winning gelaterias. If you prefer nature to eating and shopping, you can walk up to the fortress to get jaw-dropping views (and photos) of the rolling Tuscan terrain.

Like so many hilltop towns in central Italy that were once Etruscan settlements, Volterra exudes a magical kind of energy. Brought to the world's attention thanks to the "Twilight" books and movies, Volterra possesses a particular Medieval beauty. Palazzo dei Priori, Volterra's city hall, is a masterful edifice with a clock tower from the 13th Century, so handsome that the city of Florence purportedly copied its design for Palazzo Vecchio. Stone houses line the curving streets, where curated boutiques invite you to deplete your life savings with their gorgeous food items, leather goods, unique clothing and jewelry, and incredible alabaster products. The alabaster is local, and there is no shortage of workshops in town where you can see dust-covered artisans working their craft. If you are a fan of ancient history, you'll want to visit the Roman theatre, the ancient Etruscan wall and gates, and the Etruscan Museum. The views from Volterra are amazing, as is its iconic Medicean fortress.