Settle into a medieval castle to explore the history, culture, and cuisine of traditional Tuscany. In the company of a kids coordinator and our expert, immerse your family in the lively towns of Siena and Pienza, discover charming hilltop villages, make your own frescos, and play bocce and soccer with locals. Then experience the pageantry and exhilaration of the Palio, a bareback horse race that has been held in Siena since medieval times.
Stay in an 800-year-old castle set on 600 acres of parklands in the Tuscan hills.
Watch the thrilling Palio, a medieval bareback horse race in the heart of Siena.
Learn to play bocce, create your own fresco with an artist, and suit up for a game of soccer with local kids.
Make pizza and pasta with our own castle chef.
Sample homemade gelato in Florence and local vintages in Montepulciano.
Itinerary - 10 Days
Days 1 & 2 — U.S./Florence, Italy/Gargonza
Depart on an overnight flight to Florence. Upon arrival, travel to the hamlet of Gargonza and settle into a private 13th-century castle—your home for the next seven nights. Superbly situated in the Tuscan hills, Gargonza is an ideal starting point for our excursions. Meet new friends at a welcome dinner tonight. Castello di Gargonza (D)
Day 3 — Siena
Spend today discovering historic Siena. The winding lanes of this beautiful Tuscan city shelter Gothic churches, stunning palaces, and distinctive red-brick homes. Explore the Piazza del Campo, a shell-shaped plaza that has been the center of life in the city for centuries. See fascinating frescoes at the Palazzo Pubblico and venture into the massive, unfinished cathedral. Enjoy lunch on your own before returning to Gargonza for an afternoon swim at the pool. Castello di Gargonza (B,D)
Day 4 — Pienza/Montepulciano
Take a morning walking tour of Pienza, a 15th-century hill town built to exemplify the ideal Renaissance city. After lunch, drive past fields of sunflowers to charming Montepulciano. Adults may sample vino nobile at a wine tasting while the kids go on a scavenger hunt. Castello di Gargonza (B,D)
Day 5 — Arezzo
Enjoy a morning to explore the castle and its grounds before lunch. Then wander through the lively town of Arezzo, a medieval and Renaissance town known for its native son, the poet Francesco Petrarch. Later, suit up for a soccer scrimmage with local kids, followed by a picnic dinner with our soccer hosts. Castello di Gargonza (B,L,D)
Day 6 — Gargonza
This morning, join the locals for a lesson in the ball game bocce. Learn to make pasta and pizza from our own Chef Andrea. Later, enjoy a poolside game of family Palio or take a stroll in the gardens. Castello di Gargonza (B,L,D)
Day 7 — The Palio
Witness one of the world's most spectacular pageants: Siena's Palio. Divided into contrade, or neighborhoods, since medieval times, Siena brims with color and spirit during the Palio. Arrive this afternoon in time to meander through the feverishly busy courtyards, piazzas, and streets as competing contrade make their final preparations. In the late afternoon, take a seat in the stands high above the 60,000-spectator throng to see the fanfare of each contrada as it parades around the track. Then experience the exhilarating finale: a wild, bareback horse race around the Piazza del Campo. Castello di Gargonza (B,L,D)
Day 8 — Gargonza
Explore the lovely rolling hills of Tuscany on foot today. A walking tour takes us through the scenic landscape around Gargonza and introduces us to country life in a way—and at a pace—few tourists ever experience. Later, kids join a local artist to make their own frescoes. This afternoon, swim, play bocce, or go on a photo shoot with our expert. Castello di Gargonza (B,L,D)
Day 9 — Florence
Travel to Florence today. On a walking tour, visit the Accademia to view Michelangelo's masterpiece "David," and enjoy a gelato tasting. Celebrate our Tuscan adventure at a farewell dinner tonight. Hotel Brunelleschi (B,D)
Day 10 — Florence/U.S.
After breakfast, transfer to the airport for your return flight. (B)