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. Walk down the bridge over Arno and see the sun illuminating the city with different moods or choose to shop in high-end boutiques or bustling pop-out markets. After today’s adventures, 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 towards Impruneta. You’re on your own now, but you can always call our local contacts if you happen to have an issue that 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. Get ready to cycle the panoramic Wine Route (Strada del Vino) in the heart of "Chianti Classico" area. 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 products. 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 the list of today's itineraries is Meleto's Castle; it’ll be easy to find—it’s the beautiful Tuscan villa perched upon the hilltops. Take 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. Visit the elaborate architecture of its Cathedral, walk through its historic center or through 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.