Tuscany and Umbria Family Adventure

  • 8-day family adventure designed for travelers of all ages
  • Explore the medieval cities and hill towns of Tuscany and Umbria with scavenger hunts, cooking and art lessons, and vineyard tours

Expedition Details


Introduce your family to Italian history, art, and culture as you venture from the Renaissance city of Florence to the cypress-dotted landscapes of Tuscany and Umbria. Choose from a variety of family-friendly activities while exploring picturesque hill towns, beautiful abbeys, and fresco-adorned churches. Climb the medieval towers of San Gimignano, discover the treasures of Siena and Assisi, and get a hands-on watercolor lesson in Pienza. Along the way, visit rolling vineyards and centuries-old farmhouses to enjoy private wine tastings and hearty Italian cuisine. At night, unwind in charming hotels perfectly situated to embrace the area's natural beauty.

Trip Highlights

  • Explore medieval hilltop towns and traditional farms in Tuscany and Umbria and sample gelato, pecorino cheese, and other local delicacies.
  • Set off on a scavenger hunt in San Gimignano, learn to make Italian pizza, paint ceramics in Deruta, and enjoy cooking lessons with a local chef.
  • Try your hand at flag throwing, part of the pageantry of the Palio, Siena’s centuries-old horse race.
  • Discover the winding passageways of Castellina in Chianti and the ancient Etruscan ruins at Cortona.

Itinerary - 8 Days

Days 1 & 2 — U.S./Florence, Italy

Depart on an overnight flight to Florence. Upon arrival, check into our hotel, a 19th-century palazzo located in Florence’s historic district. Take a short stroll to the city’s magnificent Duomo, where our adventure begins with a walking tour of historic Florence, its palaces, churches, and cobbled squares. Learn about the city’s Renaissance treasures and the artists that created them—from Brunelleschi’s Dome to Michelangelo’s “David.” This evening, we’ll gather for a fun welcome dinner featuring delicious Florentine cuisine.
Hotel Orto de'Medici (D)

Day 3 — San Gimignano/Castellina in Chianti

Travel through a landscape of cypress-dotted hills to San Gimignano, a UNESCO World Heritage site and one of Tuscany’s most beautiful hill towns. Of the 72 medieval towers that once graced the town, the 14 that remain are still an impressive sight. Sample some of Italy’s famous gelato at a local gelateria. Then kids head off with the kids’ coordinator on a scavenger hunt through the city’s winding streets while adults enjoy lunch on their own and time to explore. See the dazzling frescoes inside the Duomo, or climb one of the towers for spectacular views. Settle into our home for the next two nights, a traditional country house set amid olive orchards near the medieval town of Castellina in Chianti. Dinner is a special treat as we learn how to make pizza the Italian way!
Hotel Colle Etrusco Salivolpi (B,D)

Day 4 — Siena

Spend the day in Siena, where the winding lanes shelter Gothic churches, stunning palaces, and distinctive red-brick homes. Visit one of the contrada museums with Dario Castagno, a local expert and the author of Too Much Tuscan Sun. Dario will share stories of the legendary Palio, a bareback horse race with traditions dating from medieval times. Kids get to try their hands at traditional flag-throwing, which is part of the Palio pageantry, while adults explore the city on their own. Take advantage of an unscheduled evening in Castellina to wander through medieval alleyways and enjoy dinner on your own at one of the town’s trattorias.
Hotel Colle Etrusco Salivolpi (B,L)

Day 5 — Val d’Orcia/Pienza

Head south this morning to the hilltop Abbey of Monte Oliveto Maggiore, home to a Benedictine monastic community. Hear the Gregorian chants sung by the monks and venture into the 15th-century abbey and cloisters, which are adorned with magnificent frescoes. Then visit a traditional cheese producer to see how pecorino cheese is made. Kids enjoy a honey and cheese tasting before we gather for a picnic lunch. Continue to Pienza, a 15th-century hill town built to exemplify the ideal Renaissance city. This afternoon, arrive at our 17th-century farmhouse hotel just outside Cortona, a lovely hill town made famous by Frances Mayes’s book Under the Tuscan Sun.
Hotel Borgo San Pietro (B,L)

Day 6 — Cortona

Begin the day with a short, scenic walk to Cortona. Here, set off on a guided tour of the town to learn about its ancient Etruscan history and modern fame. After lunch, meander through Cortona on your own or head back to the hotel for a swim. Later this afternoon, we are welcomed at a nearby agriturismo set amongst rolling vineyards and olive groves, a perfect Tuscan backdrop. While the adults prepare dinner under the guidance of the chef, kids can join a local artist for a watercolor painting lesson on the terrace overlooking the endless landscape.
Hotel Borgo San Pietro (B,L,D)

Day 7 — Assisi/Deruta

Travel through the Umbrian countryside to the hillside town of Assisi. This medieval gem is the birthplace of St. Francis, patron saint of animals and founder of the Franciscan order of monks. See some of Italy’s finest 13th- and 14th-century frescoes at the Basilica of San Francesco, and soak up the serenity of this World Heritage site. Then head to the nearby town of Deruta, known for its exquisite hand-painted ceramics. Adults can tour a pottery studio, while kids learn how to paint their own ceramics. Tonight, uncover the secrets of Tuscan cuisine during a cooking lesson with a local chef. It’s the perfect way to celebrate our family adventure!
Hotel Borgo San Pietro (B,D)

Day 8 — Cortona/Florence/U.S.

Enjoy a final cappuccino at breakfast, then explore the ancient Etruscan tombs on the outskirts of Cortona. Later, journey back to Florence, and bid farewell to Tuscany as you board your return flight home.


This expedition is not currently being offered.

Activity Level

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