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Essential Tuscany: From Florence to Siena

Admire the towns you cycle by 5
Cycle from town to town on quiet roads Admire the towns you cycle by Bike through the countryside vineyards Take a picture of the tilted tower of Pisa The itinerary lets you see the magnificent Tuscan countryside
Admire the towns you cycle by

Essential Tuscany: From Florence to Siena

  • Level
  • PriceFrom 610 euros
  • DAY4 nights / 5 days

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

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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.


D1Saturday: Arrival 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.

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.

D2Sunday: Florence – Greve in Chianti 44 km/27 miles, 800 meters/2,625 ft of climbing


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.

D3Monday: Greve – Radda in Chianti 31 km/19 miles, 792 meters/2,598 ft of climbing


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.

D4Tuesday: Radda in Chianti - Siena 41 km/25 miles, 756 meters/2,480 ft of climbing


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.

D5Wednesday: Departure from Siena


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 & Pricing

  • Option A
  • 4 nights in 3-star properties

  • 610 euros per person in April and October. Single supplement is 150 euros
  • 630 euros per person in May, June and September. Single supplement is 155 euros
  • 660 euros per person in July and August. Single supplement is 160 euros
  • Option A+
  • 1 night in a restored medieval castle and 3 nights in 4-star properties

  • 820 euros per person in April and October. Single supplement is 150 euros
  • 840 euros per person in May, June and September. Single supplement is 355 euros
  • 865 euros per person in July and August. Single supplement is 360 euros

These prices include:

  • 4 nights’ accommodation (as described above)
  • Daily breakfast
  • Meeting with our local representative
  • Luggage transfers
  • Marked maps and/or cue sheets and route notes
  • Smartphone app. (Android and iPhone) with downloadable directions/roadbook (no data necessary) - A cellphone holder is provided
  • Tourist information
  • Assistance if necessary (you will be provided with our local rep’s mobile number)
  • All tax and service charges

These prices do not include:

  • Nominal city taxes, to be paid in cash directly at each hotel (total of approx. 10-13 euros).
  • Expenses of a personal nature
  • Travel insurance
  • Bicycle rentals. Hybrid bikes are available at the rate of 90 euros per bike. E-bikes are available at the rate of 190 euros per bike (this price includes the drop-off fee for the bike's return to Florence).

Suggested Cycling Trips