Home > Tuscany’s Jewels and Treasures
For leisurely riders, Jewels and Treasures is perhaps the best way to enjoy Tuscany on an independent cycling tour. You will travel on a variety of routes, experiencing all the wonders Tuscany has to offer; from fine panoramas to culture and of course, their delicious cuisine! This unique route starts in Florence, and passes through Siena via the road of wines. The end to this spectacular adventure is none other than the famous Leaning Tower of Pisa! During your adventure, you will enter bustling, medieval cities, preserved Tuscan towns, and rich hillsides filled with wineries. This 8-day adventure is perfect for small groups and individuals looking for pleasurable, less rigorous routes within Tuscany's borders.
For travel and cycling tips to Tuscany, visit our "travel and cycling tips" section.
Land in the historic city of Florence, Tuscany's capital known for its wealth in culture, architecture, and art. This bustling metropolis is considered the birthplace of the Renaissance and from the moment you arrive, you will immediately see hints of artisan decor embellished upon buildings and plazas. You will be spending the night here, so you may want to visit some of its more prominent sites, such as Santa Maria del Fiore, Giotto's Campanile, Piazza della Signora, and the shops at Ponte Vecchio.
It's time to start your journey! After ensuring that your biking essentials are all in place, take a stroll around Florence, and then set off on your journey! Your first stop is Impruneta, a neighboring district filled with terracotta art. Here, you'll discover Gothic-inspired buildings and the town's gem, the Sanctuary of Santa Maria. After ten kilometers (6 miles), you'll reach a small town by the hills called Mercatale, where you will have wine-tasting opportunities from its local wine cellars. Wander around Palagio castle and then head onward to your hotel in Greve.
Today you will discover Tuscany’s “road of wines” (Strada del vino)! Pedal off from the Greve public square where the famous Chianti Classico Wine Festival is held every year in September. As you go on, you'll get a glimpse of the Montefioralle village, a medieval town, and Panzano, a lush green district with a countryside charm. Radda in Chianti is up next; this classic Chianti village is nestled inside the verdant hill regions and cradles remnants of the Etruscan age. From here, you can view the Pretorio Palace, discover wine tours, and enjoy a leisurely stay at a nearby hotel.
After a restful night in the pastoral hills of Chianti, you will now move on to your next destination: Siena. The first stop is Meleto's Castle, a stern-looking architecture tucked in the elevated, tree-covered lands. At Castagnoli, you will view yet another fortress, the Castle of Brolio, home of the Ricasoli family and a well-managed wine cellar. A sip of the local wine will fire up your senses, inspiring you as you go along your route. Siena is just ahead; easily distinguish by old brick buildings and the crown of Torre del Mangia. Slow down and enjoy the views, as you will spend the night here.
By taking the olden paths of Via Francigena, you'll be welcomed by the views of Mount Maggio and the castle of Monteriggioni, Dante's subject in his famous literary pieces. Abbadia a Isola is your next stop, famous for its nostalgic architecture. Proceed towards Colle Val d'Elsa, Italy's Bohemia, an industrial village known for its artisan glassware. Walk around the workshops and indulge in the local culinary offerings.
Launch today's ride with a visit to San Gimignano-—a hilltop village offering medieval landscapes. This UNESCO-awarded walled village is known for its many towers. Follow the Via Francigena and arrive at Volterra, a Tuscan industrial city famous for its alabaster works. The rather imposing setting offers a legitimate, medieval air, but don't be intimidated by its large walls and architecture. Instead, take some time and enjoy the local sights, such as the Roman theatre and the Museo Etrusco Guarnacci. Admire the sunset as you lodge in your hotel and enjoy the rest of the day as you wish.
On the last part of your independent cycling tour, you'll be departing from Volterra and heading towards the famous city of Pisa. Your ride will take you through olive groves and vineyards, perfect for an immersion with nature. After a two-hour ride, you'll arrive in Calcinaia, a quiet municipality by the banks of the Arno River. Pontedera is just a few kilometers away. This rather modernized district is home to the wine company Castellani and a sweets factory called Amedei. You may take a break from pedaling; here, you'll have a train transfer to Pisa, where you'll be spending your night.
On the last day of your tour, you can wander around the city after breakfast. Make sure you drop by some of Pisa's most famous highlights, such as the Leaning Tower, the Piazza del Miracoli, and Regatta of St. Ranieri—famous for its boat race. Dive into the city's wealth of art and gastronomy before you leave.
2 night in 4-star hotels and 5 nights in 3-star hotels
6 nights in 4-star hotels and 1 night in a 3-star hotel