Tuscany and Umbria Family Adventure

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 lush vineyards and traditional farms and enjoy private wine tastings and hearty Italian cuisine. At night, unwind in charming hotels perfectly situated to embrace the area's natural beauty.

Days 1 & 2 — U.S./Florence, Italy

Depart on an overnight flight to Florence. Upon arrival, check into our hotel, which was once part of a sturdy medieval palace. Climb its 13th-century tower to catch a glimpse of the city’s magnificent Duomo and red-tiled roofs. Then begin your family adventure with a walking tour of the historic center and get acquainted with Florence’s architectural treasures and legendary Renaissance artists. This evening, gather for a festive welcome dinner featuring delicious Florentine cuisine.
Hotel Torre Guelfa (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. Later, continue to Castellina in Chianti, our home for the next two nights. Dinner is a special treat as we learn how to make homemade pizza!
Hotel Colle Etrusco Salivolpi (B,D)

Day 4 — Castellina in Chianti

Continue south into the vineyard-laced Chianti region, stopping at Castello di Brolio. Take a tour of this castle and winery owned by the Ricasoli family, who have been credited with blending the first official Chianti. Later, arrive at the renowned Badia a Coltibuono vineyard abbey in time for a picnic lunch and sample the estate’s homemade wines, honey, vinegar and olive oil. After returning to Castellina in Chianti, kids set off on an adventure to explore the town’s medieval passageways, while adults can savor the region’s celebrated wines at a private wine tasting. Tonight, enjoy a family dinner on your own at one of Castellina’s trattorias.
Hotel Colle Etrusco Salivolpi (B,L)

Day 5 — 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 can explore the city on their own. Later, journey south into the evocative clay hills known as the Crete Senesi, and settle into our charming country hotel. Enjoy a hearty Tuscan dinner at a nearby agriturismo.
Albergo Le Terme (B,D)

Day 6 — Val d’Orcia/Pienza

Drive to the hilltop Abbey of Monte Oliveto Maggiore, home to a Benedictine monastic community. Hear the Gregorian chants sung by the monks and explore 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. Here, kids are in for another treat, as they join an artist for a watercolor painting lesson with the lush Tuscan countryside as their inspiration.
Albergo Le Terme (B,L)

Day 7 — Montalcino/Cortona

Begin the day with a scenic walk to Bagno Vignoni, and visit the village’s Etruscan-era thermal baths. Then drive to the hill town of Montalcino, home to the Brunello vineyards that produce the famous wine of the same name. Take a tour of the historic Fattoria dei Barbi winery, where the same family has been making wines since the 18th century, and learn about the region’s rich history of viticulture. Kids enjoy an adventurous scavenger hunt before we gather for lunch at a local osteria. This afternoon, continue to our 17th-century farmhouse hotel just outside Cortona, a lovely hill town made famous by Frances Mayes’s book Under the Tuscan Sun.
Hotel San Michele (B,L,D)

Day 8 — Assisi/Deruta

Travel through the Umbrian countryside to Assisi, dramatically perched on the slopes of a mountain. This medieval town is the birthplace of St. Francis, patron saint of animals and founder of the Franciscan order of monks. Visit the Basilica of St. Francis, home to some of Italy’s finest 13th- and 14th-century frescoes, and soak up the serenity of this UNESCO World Heritage site. Then explore the nearby town of Deruta, known for its exquisite hand-painted ceramics. Adults can tour a local pottery studio, while kids learn how to paint their own ceramics with a local artist. 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 San Michele (B,D)

Day 9 — 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.
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