Home > Chianti Explorer via Florence and Siena
Cycling in Tuscany is a bit like being transported through a time machine. At every turn in Florence and Siena, you might expect to encounter innovative thinkers, wealthy wine drinkers, or anyone dressed in Renaissance garb.
Out in the countryside, you’ll wonder at the immaculate landscape that appears to have been passed by altogether by the modern world. The gentle green slopes of the countryside are covered by a patchwork of vineyards and olive groves, stitched up by strings of cypress trees and topped by pristine, golden-hued villages. The sun-drenched vineyards provide an inviting place to sip and savor the local Chianti wines!
Although this is not a challenging itinerary (it’s easy-to-moderate), cyclists should be accustomed to a regular fitness routine to fully enjoy their rides up and down Tuscany’s rolling hills.
Special departure dates may be possible for groups of 5 or more (on request).
For travel and cycling tips to Tuscany, visit our "travel and cycling tips" section.
By Tuscan standards, Siena is a fairly big city and easily accessed by train from Florence and Pisa, whose airports are serviced by low-cost airlines. Experience a “time warp” as you cross from the modern city to the historic center, where university students and stylish citizens gather as always. Here, amid the winding medieval streets and in the oval Piazza del Campo, you may stumble upon a festival or the famous Palio horse race. Don’t skip the Duomo, which, despite its mind-boggling marble exterior, is technically unfinished.
From Siena, you’ll ride north — and uphill — to Radda-in-Chianti. This beautiful walled town overlooks the vineyards that produce remarkable wine. Within its walls, in the pedestrian quarters, you’ll find small shops selling local produce: cheese, wine, and salami. What else could you need for a late afternoon picnic?
Your detailed directions will take you through typical Tuscan postcard scenery. As you ride past the occasional home of creamy stone and red tile roof, pause to enjoy the view — yes, this really is someone’s everyday view! If that’s not enough to make you want to quit your job and buy a small vineyard in Tuscany, maybe you’ll make that decision over a glass or five of wine. Greve-in-Chianti, a major wine center, and Chianti’s unofficial capital will be your home for the night. Make room in your luggage for a few bottles and we’ll transfer them for you each day!
What goes up must come down, and so your up-and-downhill route over Tuscany’s finest features brings you down into Florence on the Arno River. Florence, where the Renaissance flourished and artists of great renown studied (and still study!), is home to works by Michelangelo and Leonardo da Vinci, among others. Masterpieces can be viewed in a number of places, including the Accademia dell'Arte del Disegno, the Palazzo Vecchio, or the Uffizi Gallery. There’s no need to rush to see them all as you’ll stay in Florence for two nights.
Today, you will trade in the city bustle for the quieter life of the Tuscan countryside and its tiny villages. Feel the calm settle over you as you pedal past wooded areas and olive groves galore, stretching over the rolling hills. Along the way, the hilltop village of Lucignano is quite a sight, the design of the medieval town based on a series of concentric circles.
Not far from here, a different hilltop village is your destination for the night. Known as the western gateway to the Chianti region, Tavernelle gets its name from the ancient taverns that provided food and accommodation in Roman times, as travelers made the journey from Florence to Siena, and on to Rome. As you ride, you continue the tradition!
This ride will first take you to Certaldo which we suggest you explore a bit, whether you cycle up the old town or take the cable car from nearby the train station. Look out over the hills and in the distance, your destination awaits! Pedal to San Gimignano, another immaculate Tuscan town (and UNESCO World Heritage Site) known for its distinctive tower-filled skyline. Continue on to Colle Val d'Elsa, a center famed for its crystal glassware production.
Enjoy your time in Colle Val d’Elsa exploring the fantastic medieval center and/or visiting one of the graceful 16th and 17th-century palazzos (home to the local nobility). An epic day of cycling will conclude your extraordinary weeklong holiday through history. You can take your time soaking in the Tuscan sun or rush back to Siena for an afternoon at your leisure.
After breakfast, depart at the time of your choice.
7 nights' accommodation in 3-star properties and guesthouses
Note: Special departure dates may be possible for groups of 5 or more (on request)