Home > Essential Tuscany: From Florence to Siena
If you desire to explore the best places in Tuscany but are short on time, this 5-day independent cycling tour is for you.
This shorter, condensed trip from Florence to Siena will not deny you the charms of either city or the adventure you will experience between the two. From Florence, you can soak in the Renaissance air by stopping at some of the well-known museums and galleries. You will be traversing the "Road of Wines" eventually arriving in the pastoral hills of Chianti where you can have a legitimate Italian countryside dining experience. There will be rivers, villages, churches, castles, and forts as you navigate your way from town to town and plenty of picture-perfect opportunities to take home when your tour ends.
For avid riders, we recommend our challenging Expresso Tuscany tour from Florence to Siena, or our 6-night/7-day Giro of Tuscany which also starts from Florence.
For travel and cycling tips to Tuscany, visit our "travel and cycling tips" section.
The first stop on your adventure: Florence. Drop off your luggage at your hotel and take a stroll in the old-world, artistic beauty of one of Tuscany's best gems. With a convenient and organized transportation system, you can travel with ease. Visit the giant Duomo, drop by the Uffizi Gallery or discover hole-in-the-wall bars and cafes for a gastronomic treat.
Stroll down the bridge over the Arno River and watch the sun cast its spell over the city or shop in high-end boutiques or bustling pop-out markets. After today’s adventure, it's time to relax and unwind in your hotel, as you prepare for tomorrow’s journey.
In the morning, start your adventure by getting equipped with your bike! Pass by Florence's main streets and say goodbye to the busy, sentimental city as you head your way towards Impruneta. You're on your own now, but you can always call our local contacts if an issue arises.
You will reach Mercatale after 10 kilometers (6 miles) of biking; this little town offers a peek into the Chianti countryside and a taste of the local wine varieties. Explore the Palagio Castle and visit its cellars for a unique drinking treat.
Depending on your hotel options, you’ll overnight in Greve or its countryside.
Take the road from Greve and head on towards your next destination: Radda in Chianti. The rustic charm of this hilly village is like a scene that popped out of a postcard. Glide along the road and discover well-preserved villages with fine shops, filled with the best wine and other local produce.
Pass by the baroque villages of Montefioralle and Panzano. Breathe in the fresh air, and enjoy a picnic with your friends during one of your stops; otherwise, experience the local cuisine at a trattoria for a little feast. Press onward to Radda, your home for the night.
Topping off today's itineraries is Meleto's Castle; it'll be easy to find--it's the beautiful villa perched on the hilltop. Make a few stops at the local wineries and enjoy some snacks along the way! If you manage your time well, you can reach Piazza del Campo by noon--just in time for lunch--so dig in and enjoy a sumptuous meal in the town's famous eateries.
From here, stroll around Siena to your liking. Admire the elaborate architecture of its Cathedral, or walk through its historic center and its links of museums and parks.
Make your way to your hotel and let your legs rest from days of leisurely pedaling.
After breakfast, you can spend your last moments as you wish.
Then pack up your luggage and move on to the next stage of your journey. Perhaps you wish to travel back to Florence--a mere one-and-a-half-hour train ride from Siena; or move further towards another Italian metropolis, such as Milan or Rome--both cities are also well-serviced by train.
Make sure to bring a souvenir with you; small shops offer quality commodities at great prices—just the thing to mark the end of your independent Tuscan cycling trip.
4 nights in 3-star properties
1 night in a restored medieval castle and 3 nights in 4-star properties