Travel Guides: Italy Travel Guide: Overview
In Southern Europe—right in the heart of the Mediterranean—lies a boot-shaped country stuffed to the brim with culture, history and fine cuisine.
Tuscany scores top marks for family fun. Enjoy miles of smiles on kid-approved routes. Discover ancient hill towns and climb a medieval tower (fueled by gelato, of course!). Chianti tasting for the adults. Hands-on pizza making for the youngsters. Your perfect family adventure... in Toscana!
THIS ITINERARY: 6 days, 5 nights
ACCOMMODATIONS: Casual Hotels
Special Kids Prices
Start Arezzo / End Florence
Start/End locations may vary. Do not book flights until your trip details are confirmed.
Bike through the picturesque countryside of the Val di Chiana past cypress trees, vineyards, grazing sheep and stone farmhouses | Savor farm-fresh products over a family lunch | Ride to the hilltop town of Montepulciano while kids take to a high ropes course | In the evenings, have your fill of pasta, kid-friendly contorni and—for the adults—wines | Our hotel, a former medieval villa, is an ideal place for rest and play.
Originally a 12th-century residence, this hotel is depicted in a Leonardo da Vinci painting. (pool)
Follow cycling routes through the Umbrian valleys to the town of Castiglione del Lago, with views of an iconic Tuscan landscape and Lake Trasimeno | Kids sail across the lake while the grown-ups bike rolling terrain to Etruscan ruins | Step back in time as you stroll the historic streets of Cortona | Lounge poolside at our welcoming 17th-century retreat.
Once a country villa, this hotel offers spectacular views of Cortona's medieval skyline. (pool)
Ride along the Strada dei Castelli (Road of the Castles) to Radda in Chianti, known today as a major center for Chianti Classico wine production | Young artists try their hands at painting their own ceramic souvenirs in a fun art class | A memorable family dinner experience awaits as budding kid-chefs put together a well-rounded meal—pizza! | Ride scenic routes through Chianti's inviting hills | Shop for hand-painted souvenirs and admire Renaissance-style designs at Ceramiche Rampini | Visit Badia a Coltibuono (Abbey of the Good Harvest) and taste the honey produced on-site | Wonderful vistas abound during a ride through the heart of Chianti | Pause to enjoy delicious gelato in ancient towns | Celebrate a Tuscan family vacation with a meal amid the olive groves at our charming hotel.
Travel back in time at this country hotel, housed in an antique mill dating from the 15th century. (pool)
The earlier you book, the more choice you'll have and the lower your price. And you can always change your mind — you won't be charged to transfer to a different trip before your final payment is due. View cancellation policy
Click on dates for pricing, itinerary variations and to book your trip. Price is per person, double occupancy.
Every Backroads trip is designed to appeal to a wide variety of interests and fitness levels. We know your pace may vary from one day to the next—and your traveling companion's may differ somewhat from yours. So we present a range of mileage options, and each day you decide exactly what and how much you want to do. LEARN MORE.
Note: This region is known for its rolling terrain and hilltop towns. We'll flatten some of the hills by incorporting liberal van shuttling into the itinerary, and the mileage is moderate to enable you to spend more time exploring on your own.