In selecting the best destination for a Tuscany family holiday, I like to suggest that families consider above all location in proximity to the day trips you have in mind. For families visiting the area around Siena, the perfectly intact medieval fortified town of Monteriggioni is one of our favorite destinations.
So many Tuscan towns to visit, so little time. I love discovering hidden hill towns in Tuscany and Umbria, envisioning life as it may have been as we enter a new medieval gate with the anticipation of the treasures that await inside.
Visiting Monteriggioni in Tuscany with Kids
One of my top tips for exploring Tuscany is to map out the famous town you plan to visit, then stop by some lesser known hilltowns nearby, perhaps scheduling your visit during a sagra, a type of local celebration, or at least on market day.
If you are visiting Siena, pencil in a visit to the nearby hilltown of Monteriggioni, a medieval fortress town built to protect Siena from Florence during the wars between the city states. The town stands proudly lost in time along the Via Cassia, looking north toward Florence, and south toward Rome, with its imposing walls and 14 turrets famously mentioned by Dante in the Divine Comedy, looking out along the beautiful Tuscan plains surrounding Siena—the Crete Senesi. Inside you will find every classic feature of medieval towns. Travel back in time by visiting during the first week of July for the Monteriggioni Medieval Festival, or Festa Medievale, when the town transforms into a bustling medieval city with feasting, dancing, and pageantry. You even need to exchange your currency for medieval coinage when you pass through the main gate, with a drawbridge as the town was once surrounded by a moat.
Monteriggioni was a significant stop on the Via Francigena, the ancient pilgmrimage road connecting England to Rome. Visitors can stop in the tourist office for information on the significance of the town in welcoming pilgrims for centuries. It’s possible to ascend onto the fortified wall of the town to view the beautiful countryside around you, and have a birdseye view of the town itself from the vantage point of the crenellated ramparts (Christmas photo material views…).
The areas surrounding Siena are famous for the rolling hills of vineyards and characteristic Tuscany farms where tradition has produced culinary deliciousness generation after generation. When visiting Monteriggioni or staying in Siena, there are lovely options for a family lunch or farm visit nearby. Our amica, culinary expert Heather Jarman of Sapori e Saperi adventures , has a great recommendation for rustic, authentic dining in the area around Monteriggioni, famous for raising the cows for bistecca Chianina. Heather suggests visiting the working farm of Tenuta La Fratta in Sinalunga to experience noble farming life as it has existed in this area for centuries. Heather explains, “As you pass down the long avenue to La Fratta, you enter a time capsule of several centuries ago. A farm frozen in history. Here they rear the famed large white Chianina cow; the last peasant farmer died only five years ago; and the Marchioness can be glimpsed tootling around in her battered station wagon. The tour of the estate includes a tasting of the exceptionally delicious beef.”
For more tips, check out our Italy Travel Tip YouTube video on Where to Stay in Tuscany
Where to stay in Monteriggioni:
Hotel Romantik Monteriggioni
Monteriggioni, IT 53035
The Hotel Romantik Monteriggioni is a lovely historical hotel right in the town center with a pool overlooking the plains surrounding the walls, built into the remnants of the moat! The pool is set in a beautiful garden with olive trees and views of the fortified tower. They offer a 20% discount to registered pilgrims, too. Rollaway beds can be added to double rooms for children under 16 years old for 30 euro/night supplement.
Strade di Strove 33
Monteriggioni, IT 53035
Castel Pietraio is a unique agriturismo built in a medieval fortified castle and hamlet just 10 minutes from Monteriggioni and 30 minutes from Siena, with beautiful views looking out over the Colli Senesi area of Tuscany. The hotel offers double rooms and suites as well as one-, two-, and three-bedroom apartments. The property includes the surrounding land, cultivated with vineyards and olive groves. Amenities include a swimming pool, BBQ area, and children’s playground. Shops and dining are available in the village, walking distance from the rooms and apartments.
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