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Essential Tuscany: From Florence to Siena

Admirez les villes que vous traversez à vélo 4
Cycle from town to town on quiet roads Admire the towns you cycle by Bike through the countryside vineyards The itinerary lets you see the magnificent Tuscan countryside
Admirez les villes que vous traversez à vélo

Essential Tuscany: From Florence to Siena

  • Level
  • PriceFrom 910 euros
  • DAY4 nights / 5 days

More info: Receive detailed hotel list, bike specs, and route description

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If you want 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 traveling 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 with you when your tour ends.

For travel and cycling tips to Tuscany, visit our "travel and cycling tips" section.


D1Arrival in Florence


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.

D2Florence – Greve in Chianti Mileage: 37 km / 23 miles; Total Climb: 650 m / 2,130 ft


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.


D3Greve – Radda in Chianti Mileage: 40 km / 25 miles; Total Climb: 540 m / 1,770 ft


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.


D4Radda in Chianti - Siena Mileage: 37 km / 23 miles; Total Climb: 680 m / 2,230 ft


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.


Booking & Prices

  • Option A
  • 4 nights in 3-star properties

  • 910 euros per person in April and October. Single supplement is 240 euros
  • 925 euros per person in May, June and September. Single supplement is 250 euros
  • 960 euros per person in July and August. Single supplement is 270 euros
  • Option A+
  • 4 nights in 3- and 4- star properties

  • 1,045 euros per person in April and October. Single supplement is 295 euros
  • 1,065 euros per person in May, June and September. Single supplement is 315 euros
  • 1,145 euros per person in July and August. Single supplement is 340 euros

These prices include:

  • 4 nights’ accommodation (in 3- and 4-star properties)
  • Daily breakfast
  • Luggage transfers
  • Roadbook provided as an app (when used as a GPS, no data plan is necessary)
  • Tourist information (provided as part of the app)
  • Assistance if necessary (you will be provided with our local rep’s mobile number)
  • Service charges and most taxes

These prices do not include:

  • Visitor/tourist taxes, to be paid directly at each hotel
  • Expenses of a personal nature
  • Travel insurance
  • Bicycle rentals. Hybrid bikes are available at the rate of 120 euros per bike. E-bikes are available at the rate of 195 euros per bike. Gravel bikes are available upon request

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