Spend two weeks exploring northern Italy at your own speed with this self-drive itinerary that allows you to choose the stops. You'll start off in the northern lakes, with Lake Como and Lake Garda offering boat tours past villas and amusement parks alike. Then make your way into Tuscany, where you'll ride a horse-drawn wagon through the countryside and explore the medieval walled city of Siena and famous art of Florence. Finish your trip in the Italian Riviera and colorful five villages of Cinque Terre.
Our two recommended routes include family-friendly spots in the Chianti Valley, exploring either the Val D’ Elsa around San Gimignano or the Val D’ Orcia around Pienza and Montepulciano. Regardless of which route your choose, you’ll marvel at the incredible natural scenery, surrounded by olive groves and vineyards that make up the typical hilly landscape. The routes are a combination of main roads and hilltop lanes weaving through the Tuscan countryside.
Read more about family-friendly excursions in Italy.
Suggested Routes and Villages:
#1: Exploring Chianti and Val D’ ElsaIf you decide to explore the picturesque villages to the north of Siena, San Gimignano (a UNESCO World Heritage Site) should be on the top of your list.
- Take the Via Francigena (the ancient pilgrimage road connected with Rome), which leads through the town from Porta San Giovanni to Porta San Matteo (ancient gates). You'll pass through Piazza della Cisterna, a grand square surrounded by the Palace of the Podestà and the Salvucci Towers and Piazza Duomo. Kids love San Gimignano’s famous gelaterias, which have an earned reputation for producing some of the best flavors of gelato in the world. For history, visit the San Gimignano 1300, a family-friendly museum depicting the city as it existed in 1300 CE.
Close to San Gimignano, you can stop at the Archeodromo in Poggibonsi, an excavated archaeological dig spanning three eras. The site includes an excellent park area for picnics and playing. Though you can walk around the park and the digs at any time, the living museum is only active on Sundays.
- Another idea for families and kids is Rocca di Staggia, a fantasyland adventure! Once you're finished with the castle, take a few minutes to walk through the small and sleepy town of Sense Staggia. Shops and restaurants are open every day from 10 AM- 7 PM and don’t close for lunch.
- Along this route is the impressive medieval fortress called Monteriggioni. The intact castle walls surround this town perched on a hillside and are a sight to behold. Take in the views, have a coffee, and enjoy wandering around the porticos and piazzas in the charming historical center before heading toward the Chianti Valley.
#2: Exploring Montepulciano & Villages
If you decide to explore the picturesque villages to the south of Siena, you can start from Montalcino.
After a relaxing morning in Montalcino, we recommend taking the slightly longer route along the S2 road, which is 27 miles (43 km) and features the Sant Antimo Abbey in the Val d’Orcia National Park. This ancient mystical Benedictine abbey is set in a peaceful natural landscape. Unknown and unseen by many travelers, it's one of the main wonders of Tuscany! Very close by, you can visit the Giardino di Daniel Spoerri in Seggiano, an excellent playground substitute.
- Pienza is a cozy town known for making delicious Pecorino cheese. Once you park, take a walk into the village center to see the magnificent Piazza Duomo (the square of the cathedral), overlooked by the beautiful Piccolomini Palace. Stroll along Corso Rossellino, the main street named after the Florentine architect who designed most buildings. Pienza is a great place to relax and enjoy the slower pace of rural life as you sit down for a coffee at a cafe. You can expect to find pecorino and extra virgin olive oil on nearly every menu!
- For a fun, tasty, and educational activity, head to Cugusi, the famous cheese-making area close to Pienza. Stop at the Cugusi Dairy, where adults can stock up on the famous local Pecorino cheese, and kids can learn all about the fascinating cheese-making process, including a little meet and greet with the animals. For a slow-paced afternoon at a local farm with a picnic lunch, spend a few hours relaxing, eating, and watching the animals at Podere Il Casale.
- Another great idea for an afternoon stop is at the gardens of La Foce with a 45-minute tour. Afterward, go for a casual outdoor dinner at Dopolavoro La Foce. There's a full-service restaurant inside and a beer garden with hammocks, ping pong tables, and plenty of open space for an evening outdoors.
- Montepulciano is known for its wine, and you should not miss out on discovering the secrets of the local grapes. Once you’ve wandered through the charming streets, enjoy a late Italian lunch accompanied by Vino Nobile di Montepulciano. The family and kid-friendliest wineries in Montepulciano are Palazzo Vecchio and Il Loggio in Cortona.
Itineraries with Explore Tuscany with Kids
Northern Italy Family Road Trip: Florence, Chianti, Italian Riviera, Lake Como & Lake Garda - 10 Days
Wheel your way through northern Italy on this road trip with stops that school-aged children and parents can enjoy, with timing adjustable to your own preferences. You'll start amid the Renaissance influences of Florence, then set out into the Tuscan countryside and Chianti Valley on winding olive- and vineyard-lined roads. From there, head to the coast to wander the beaches of the Italian Riviera and then up to Lake Como to explore its luxurious shores. Wrap up your Italian sojourn on the playful shores of Lake Garda before you return to Florence.
Families with teens who want to get out and explore (and find the perfect backdrop for their photos) should give this two-week itinerary through the Veneto and Tuscany a try. You'll start in Venice, where you can explore secret passages, craft your own masks, and paddle a gondola. Then head to Verona and Lake Garda, biking through both urban and natural attractions. Wrap up in the Tuscan cities of Siena and Florence with a hot air balloon ride, gelato-making, and more.
Your whole family can fully engage with Italy on this adventurous itinerary, ideally suited for teens with energy to spare. You'll begin in Venice, where you'll craft Carnival masks and explore the secret passages of the city's famous landmarks. After a stop to wander the streets of Verona, you'll head to the park-lined shores of Lake Garda, filled with attractions for all ages. Finish the tour in the Tuscan city of Siena, your base for hot air balloon rides, hikes, and more.