Itinerary :

Day 1: Arrive in Siena.
You can easily reach Siena by train from Florence and Pisa. We suggest an arrival that gives you some time to explore this fascinating city, perhaps during the sunny afternoon. Siena’s Duomo was intended to be the largest cathedral ever, but funds ran out – you can see the wall to where it would have been extended. Your mouth will drop when you consider the enormity! Nearby, you’ll find the Piazza del Campo, a public square where the Palio horse race occurs, pitting Siena’s districts (wards) against each other. Spend a pleasant evening sampling Tuscan delicacies and gearing up for tomorrow’s ride.

Day 2: Siena – Radda-in-Chianti – 43 km (or 27 miles)
Onwards and upwards to Radda-in-Chianti, a beautiful walled town surrounded by vineyards. Guess which famous Italian wine is produced here! Within this perfect medieval village you’ll find a welcoming pedestrian quarter. The family-run shops sell local produce like salami, cheese, and – no surprises – wine. What else do you need for a late afternoon picnic? You’ll be in Radda-in-Chianti for the night, so you can always enjoy a glass of Chianti with dinner!

Day 3: Radda-in-Chianti – Greve – 40 km (or 25 miles)
Follow your detailed directions through picture-perfect Tuscan scenery. Tuscany, or Toscana, is Italy’s most-photographed region; you’re likely to follow suit with your own camera! At the end of the day, you’ll be in Greve, Chianti’s unofficial capital and major wine center (again, no surprises!). The antique city center, a triangular piazza, is home to an ages-old marketplace surrounded by medieval buildings. On the outskirts, you’ll find the manor homes of explorers Verrazzano and, it is claimed, Amerigo Vespucci.

Day 4: Greve – Firenze (Florence) - 38 km (or 24 miles)
Taking the hilly route through the Tuscan countryside has its rewards: after a few ups and downs, you’ll be in Firenze (known as Florence in other areas of the world). Needless to say, this world-renowned city offers visitors plenty to see and to do! In the birthplace of the Italian Renaissance, you can wander amongst grand buildings like the Duomo, and visit works of art in nearby galleries and churches. Don’t worry about rushing through Florence – you’ll have a rest day in the city tomorrow.

Day 5: Rest-day in Florence (Firenze)
After a few days of tranquil travels through Tuscany, the excitement of city life will keep you on your feet. That, and you’ll probably be visiting all the famous masterpieces scattered throughout the city. Don’t be fooled – the David outside the towering town hall (Palazzo Vecchio) is just a copy. The Accademia dell’Arte del Disegno is home to Michelangelo’s true David while the celebrated Uffizi Gallery is where you’ll find Botticelli’s The Birth of Venus, among other famous paintings! You can enjoy gelato while you stroll past the artisan shops on the Ponte Vecchio, or if you’d prefer, we can recommend a great guided tour of Florence.

Day 6: Florence (Firenze) to Colle Val d'Elsa - 40 km (or 25 miles) by train + 27 km (or 17 miles)by bike
Wake up in one UNESCO World Heritage Site, only to ride to another; you’ll be visiting San Gimignano, a city no less amazing than your starting point. First you need to take a short train ride to Certaldo, which by itself is a lovely medieval town. From there, let the skyline be your guide to San Gimignano, a perfectly-preserved town with multiple medieval skyscrapers. You can climb the Torre Grossa for out-of-this-world views. Down on terra firma, you can find a number of unbelievable restaurants set in historic buildings that your taste buds are sure to remember for years to come.

Day 7: Colle Val d'Elsa – Siena – 37 km (or 23 miles)
There’s nothing like an epic day of cycling through pristine, postcard-worthy scenery to conclude an extraordinary week-long holiday. You don’t have to rush through the day – just enjoy it at an Italian pace. Depending on the time you arrive back to Siena, you may have time to check out things you missed or pick up some souvenirs. Your last tour night will be spent in Siena.

Day 8: Departure
After breakfast, depart at the time of your choice.