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Essential Tuscany: From Siena to Florence

Admirez l\'architecture impressionante depuis votre selle en suivant cet itinéraire 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 l'architecture impressionante depuis votre selle en suivant cet itinéraire à vélo

Essential Tuscany: From Siena to Florence

  • Level
  • PriceFrom 480 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 Siena to Florence lets you explore the charms of both cities and enjoy a cycling adventure whilst riding between the two! From Siena, 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", passing through the pastoral hills of Chianti where you can have an authentic Italian countryside dining experience, before arriving into the magnificent capital of Tuscany, Florence. There will be rivers, villages, churches, castles, and forts along the way, as you navigate your way from town to town, and plenty of picture opportunities to take home with you when your tour ends.

For our avid riders, we recommend our challenging 6-night/7-day Giro of Tuscany, starting in Pisa and finishing in Florence.


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


D1Tuesday: Arrival in Siena


The first stop on your adventure: Siena. Enjoy strolling around this beautiful city. Visit its Cathedral and marvel at the elaborate architecture, walk through its historic center, which is classed as a UNESCO World Heritage Site and take in its numerous museums and parks. Be sure to enjoy some of the local cuisine as well – Siena is famed for its gastronomy! After today’s adventures, it's time to relax and unwind in your hotel, as you prepare for tomorrow’s journey.

D2Wednesday: Siena – Radda in Chianti Long Option; Mileage: 45 km / 28 miles Total Climb: 880 m / 2,887 ft Total Descent: 700 m / 2,297 ft; Short Option; Mileage: 37 km / 23 miles Total Climb: 680 m / 2,231 ft Total Descent: 500 m / 1,640 ft


In the morning, start your adventure by getting equipped with your bike! From Siena you will head north towards the beautiful village of Radda in Chianti. Along the way you might like to make a few stops at local wineries and enjoy some snacks. Topping off the list of today's itineraries is Meleto Castle; it’ll be easy to find—it’s the beautiful Tuscan villa perched at the top of a hill! Wend your way on to Radda in Chianti, a beautiful hilltop village and your home for the night.

D3Thursday: Radda in Chianti – Greve Long Option; Mileage: 40 km / 25 miles Total Climb: 540 m / 1,772 ft Total Descent: 830 m / 2,723 ft; Short Option; Mileage: 18 km / 11 miles Total Climb: 200 m / 656 ft Total Descent: 490 m / 1,607 ft


Today you will discover Tuscany’s “Road of Wines” where the famous Chianti Classico wine is produced. 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 Panzano and Montefioralle. Breathe in the fresh air and enjoy a picnic with your friends during one of your stops; or experience the local cuisine at a trattoria for a little feast. The route leads you through this beautiful Tuscan countryside into Greve where you will overnight.


D4Friday: Greve - Florence Mileage: 37 km / 23 miles Total Climb: 650 m / 2,133 ft Total Descent: 830 m / 2,723 ft


Your final destination on this tour is Florence, capital of Tuscany and famed for its wealth of culture, architecture, and art. Along the way, explore the Palagio Castle and visit its cellars for a unique drinking treat before reaching Mercatale, a small town offering a peek into the Chianti countryside and a taste of the local wine varieties. Ride through Impruneta and on to Florence. Depending on when you arrive you may like to fit in a visit to the giant Duomo, drop by the Uffizi Gallery or discover hole-in-the-wall bars and cafes for a gastronomic treat. Alternatively, you may want to walk across the bridge over the Arno river and see the sun illuminating the city in different moods or choose to do some shopping in high-end boutiques or bustling pop-out markets. At the end of the day make your way to your hotel and let your legs rest from days of leisurely pedaling!

D5Saturday: Departure


After breakfast, you can spend your last moments in Florence as you wish, perhaps visiting some of Florence’s landmarks that you did not manage to fit in the day before. Then pack up your luggage and move on to the next stage of your journey. Perhaps you wish to travel back to Siena - a mere one-and-a-half-hour train ride from Florence; or move on towards another Italian metropolis, such as Milan or Rome - both cities are also well-connected 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

  • Price Details
  • 4 nights in 3- and 4- star properties

  • 480 euros per person in March, April and October. Single supplement is 150 euros
  • 560 euros per person in May, June and September. Single supplement is 155 euros
  • 590 euros per person in July and August. Single supplement is 160 euros

These prices include:

  • 4 nights’ accommodation (4 nights in 3- and 4- star properties)
  • Daily breakfast
  • Meeting with our local representative
  • Luggage transfers
  • Marked maps and/or cue sheets and route notes
  • 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 75 euros per bike. E-bikes are available at the rate of 160 euros per bike.

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