Introduce your family to the magic of Tuscany as we explore walled villages, old fortresses, and breathtaking landscapes. From our base at a lovely villa in Chianti, set out on daily adventures, discovering medieval alleyways and castle keeps, peering at famous frescoes with an art historian, and hiking through the beautiful Tuscan countryside. Learn how olive oil, cheese, and gelato are made—and enjoy a taste too!
Take in the view from the top of Siena’s Duomo, and explore the many towers of San Gimignano.
Search for truffles with a local truffle hunter in the wild landscapes of the Crete Senesi and learn how gelato is made at a gelateria in Volterra.
Venture into the crypt of a medieval castle on a special tour for kids and explore a working monastery built in the 14th century.
Go horseback riding in the Chianti hills and hike in the gorgeous Val d’Orcia with a naturalist.
Itinerary - 9 Days
Days 1 & 2 — U.S./Florence, Italy/Chianti
Depart on an overnight flight to Florence, and meet up to travel to the vine-covered region of Chianti in Tuscany. Our home here is a beautiful villa surrounded by fairytale scenery. Enjoy time to explore the grounds before our welcome dinner. Villa Campomaggio (D)
Day 3 — San Gimignano/Volterra
Venture into the magical village of San Gimignano and learn the story behind its 14 medieval towers. Wander through a maze of historic streets and discover hidden masterpieces of art and architecture. Take a walk through fragrant orchards and olive groves to a private country home, where we’re invited to a rustic feast. Continue to Volterra, where we delve into the mysteries of the ancient Etruscans, and take in sweeping views of the countryside out to the Tyrrhenian Sea. Learn about the great Italian tradition of gelato-making on a visit to a local gelateria before heading back to our villa for dinner. (B,L,D)
Day 4 — Crete Senesi/Pienza
Head into the rippling landscape of the Crete Senesi, where eroded clay deposits have left deep gullies and cliffs. Cross a drawbridge to explore the 14th-century abbey of Monte Oliveto Maggiore, filled with vivid frescoes and still inhabited by monks, and then follow a tartufaio (truffle hunter) and his dog through the nearby hills in search of coveted truffles. This afternoon, choose between two options: Join a naturalist for a hike in the beautiful Val d’Orcia, a UNESCO World Heritage landscape of fortified hilltop hamlets and villas set atop agricultural fields designed during the Renaissance. Or hit the streets of Renaissance Pienza with a guide and walk the town’s old walls to take in the views. (B, D) (B,D)
Day 5 — Siena
Spend a full day immersed in enchanting Siena with a longtime resident and art historian. Learn about the vibrant traditions of the Palio, a medieval bareback horse race that still captivates Siena every summer. See the world’s oldest bank and decipher the hidden meanings of the frescoes in the Palazzo Pubblico. Climb to the top of the unfinished Duomo, whose construction was stopped during the Black Death in 1348. In the afternoon, enjoy time to continue exploring the city at your leisure. Challenge your kids to find the multiple statues of the She-wolf suckling the twins, Romulus and Remus—the symbol of Siena. Shop for handcrafted medieval souvenirs in the alleyway shops, or visit the intriguing Museum of Torture. A chef meets us back at the villa for a fun evening of cooking followed by a feast. (B,D)
Day 6 — Exploring Chianti
This morning, strike out into the lovely countryside on a horseback ride with local equestrians. Or pay a visit to the private estate where Kenneth Branagh’s Much Ado About Nothing was filmed, to learn how olives are cultivated, harvested, and pressed into oil. Enjoy a tasting of olive oil and cheese before rest of the group arrives for lunch. Take advantage of a free afternoon at Villa Dievole to play tennis, take a walk, or relax by the pool. (B,L,D)
Day 7 — Organic Farm/Montepulciano
Travel into southern Tuscany to a family-run organic farm, where we’ll be welcomed by the whole family. Learn the art of food production in Italy as we explore the dairy, bee farm, vegetable garden, orchard, granary, vineyard, and animal stockades that house pigs, goats, and sheep. Our pen pals meet us here for a delicious picnic of fresh cheese and produce from the farm. This afternoon, walk the cobbled streets of the historic walled city of Montepulciano, discovering its palaces and fortifications. Take in a panoramic view from atop city hall before returning to our villa for a wine tasting for adults. (B,L,D)
Day 8 — Chianti Countryside/Radda in Chianti
Spend the morning exploring a nearby medieval castle. On a special tour for kids, climb down into the crypt, up into the nearly one-thousand-year-old tower, and around the ramparts. Go for a walk in a labyrinth of geometric gardens and peer at suits of armor and weaponry used many centuries ago. You may instead tour the surrounding vineyards and enjoy a tasting at the property’s wine cellars—once owned by the baron who established Chianti’s wine industry. After lunch at a private home, pay a visit to the charming village of Radda in Chianti, whose narrow medieval lanes are draped with hanging flowers. Or return to the villa for time to relax. Tonight, gather at a stunning villa near Siena for a wonderful meal with our hosts and a final salute to our Tuscan adventure. (B,L,D)
Day 9 — Florence/U.S.
Travel back to Florence Airport early this morning for your flight home.
Click here for a description of all activity levels.
About this Expedition
We tap into National Geographic’s vast network to design unique travel experiences for the whole family, filled with hands-on activities and memorable moments. A special aspect of this expedition is the Kid-to-Kid Connection, which links every young traveler with a pen pal of similar age in Italy. Meet up with your pen pals at a family farm in southern Tuscany and explore the barns, dairy, and orchards together before a delicious picnic of food produced at the farm.
Our dynamic Expedition Leaders enrich each experience with their insights, knowledge, and energy, and a Young Explorer Leader joins every group to facilitate fun activities that help kids get the most out of the places we go. As we travel, we’ll also meet up with fascinating people doing meaningful work in the field.