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Taking Florence Day Trips in Tuscany

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People often think of Tuscany as the perfect vacation destination for couples and foodies, or wine enthusiasts. While the countryside of Tuscany is romantic and certainly is rich in cooking and wine traditions, Tuscany can also be an ideal vacation with kids with a variety of day trips and things to do. While Florence is a beautiful city with many things to do, especially in the summer, it can get very hot and crowded and taking a day trip from Florence to Tuscany offers an alternative for families that are looking to round out their Tuscan experience.

Three Family Friendly Florence Day Trips

Siena, San Gimignano, and Monteriggioni are all close by  (Monteriggioni is in between the two). Depending on whether or not families have rental cars, are going with organized groups, or are taking a train, these three day trips could be seen in one day or could be split up into more leisurely visits on separate days.


Day trips in Tuscany From Florence - Siena

Enjoying a day in Siena.

Siena is a town not far from Florence (you can take the train or a bus to get there) that offers a smaller feel with a rich history and cultural tradition. Siena is most famous for the Palio in July and August, where each neighborhood competes against the others in a horse race.  The medieval city can be explored on foot easily with the main attractions being the Piazza del Campo (town square) and the Duomo. Children will love running around the Piazza and chasing the pigeons. A not just for tourist place to eat is Osteria Boccon del Prete where everything is homemade and delicious. Children can request a simple plate of pasta while the rest of the family enjoys specialties like bruschette with prosciutto and mozzarella to pici al cavolo nero. 

San Gimignano

Day trips in Tuscany from Florence - San Gimignano

Children will enjoy climbing the multiple towers, posing with statues, and eating gelato at San Gimignano.

San Gimignano is even smaller than Siena and boasts seven towers that rocket into the sky like medieval skyscrapers. Many can be climbed and provide scenic vistas over the Tuscan countryside.  Visitors to San Gimignano will appreciate frequent concerts or performances and smaller crowds than Florence and even Siena. After climbing the many steps to one more of the towers, stopping to sit and have gelato in the main square at Gelateria dell’ Olmo is a perfect way to people watch and get your daily fill of this cold treat.


Monteriggioni is a small town on a hill between Siena and San Gimignano.The town dates back formally to 1213, or even earlier as it is situated on the Via Francigena that winds between Rome and the Alps connecting a network of routes that ran from Northern Italy to what is now Tuscany. Merchants used the road as did pilgrims on their way to Rome. This is a perfect stop and thing to do for families that have a rental car, stopping to walk along the city’s walls for a unique Tuscan experience.

As picturesque as Florence is with many things to do, the best way to experience Tuscany is to add a day trip to a smaller Tuscan towns for a complete Tuscan experience.

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Our Hilton Mom Voyage team members live throughout the U.S. and have traveled by air and car all over the world with their families!

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