There is something eminently peaceful in riding through hilltop towns that have stood watch here since the Middle Ages. On this exciting family adventure, keep being a family that plays together with fun rides through the Val di Chiana, private lunches with amazing local famiglias, and bowing cypresses everywhere. You’ll also be treated to gelato tastings, medieval flag throwing, and Italian market wandering. The kids will crash early, which is fine by you… you still have a prize-winning Brunello to polish off. From idyllic Florence to lordly Montepulciano, Tuscany truly is La Dolce Vita.
Trip designed by Travel Expert Courtney MundyView Courtney’s Profile
Accompany your local guide through Florence's historic centre. She'll share tales of the Medici family, then bring you for a visit to Florence’s most famous resident, David.
Meet your guide and let her teach you about the delicious traditions of Florentine cuisine as you stroll past the markets and pastry shops. Stop at a first-rate gelateria for a glimpse at (and taste of) their perfected production techniques.
Set off on a ride through the Val di Chiana toward Tre Rose Estate, producers of vino nobile, Chianti and Brunello (all of which we’ll taste). Tonight, enjoy a feast of delicacies prepared by Amorosa’s chef.
Pedal sunflower-lined country roads to a homemade lunch at the Lungarella family’s country house (save room for Mamma Sara's tiramisú!). Tonight, explore the boutiques, art galleries, and restaurants in the hilltop town of Cortona.
Arrive in Montepulciano and sample its fine vino nobile. Your guide will introduce you to the local artisans and point you toward our favourite specialty food shops as you meander through town.
Visit the magnificent 13thC cathedral in Siena, as well as the Piazza del Campo (the location of the famed Palio horse race). Tonight, a troupe of medieval flag-throwers join us to demonstrate their ancient art form (and give the kids a hands-on lesson!).
After breakfast at the hotel, we’ll drive you to Florence train station or airport for your onward travels.Show All Days VIEW MAP CLOSE Want to see a full
In a word: everything. In ninety words? Signature B&R guides; local experts; unique, unforgettable biking and walking routes; private tours; authentic local cuisine; lessons and demonstrations; local artisanal wines; wine tastings; all victuals and libations; all the endorphins you can handle; new insight; interesting, fun and like-minded travel companions; a feeling of total freedom. In short: an extraordinary, hassle-free journey of discovery.