Tuscany cycling tour from Florence to Siena

Name: Tuscany cycling tour from Florence to Siena
Brand: Cyclando
Price: 801 EUR
Availability: InStock

Toscana

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Tour

Bike Tours, Road cycling holidays, E-bike tours, Gravel bike tour, MTB cycling holidays

Duration

5 days

Distance

174Km

Self-guided

The beauty of this package is in the freedom it offers: without a guide, you are free to decide the timing, pace, and stops of your journey. Travel freely, travel your way!

4/5 Medium-Easy

Moderate-Difficult, between 50 and 100 kilometers per day with an elevation gain between 700 and 1300 meters.

Linear

The starting point is different from the ending point, with overnight stays in different hotels and daily stages.

Description

Day 1: Florence
Individual arrival, free dinner and overnight stay in a 3-star hotel, located a few steps from the old center of Florence.

Day 2: San Gimignano (56 km, +/-1010 m)
Breakfast and meeting with our staff, who will give you detailed maps and all the information on the best approach for each single stage. The tour from Florence to Siena by bike will start with a slight climb up to Piazzale Michelangelo, one of the most panoramic and fascinating places in Florence. You will then visit Montespertoli, a pretty town located on a gentle hill in Chianti, whose surrounding countryside offers postcard landscapes. You will continue on to Certaldo alto, a splendid medieval village that was the birthplace of Boccaccio, a famous medieval writer and author of the Decameron. Finally, uphill along the Via Francigena, you will reach San Gimignano, the famous medieval village with beautiful towers. Free dinner and overnight stay in a 3-star hotel in the city center. 4-star hotel available upon request.

Day 3: Monteriggioni and Chianti (49 km, +/-800 m)
There are various places of interest in this stage. Stop at Abbadia Isola, an abbey on the edge of the Via Francigena and in Monteriggioni, one of the best preserved medieval villages, with the walls surrounding the town. Climb towards Chianti, surrounded by fine vineyards and catapult yourself into the historic struggle between Siena and Florence in Castellina in Chianti, an ancient medieval village. Dinner and overnight in a 4-star hotel located in Radda in Chianti.

Day 4: Brolio Castle and Siena (52 km, +/-820 m)
Take a tour through the alleys and walls of Radda in Chianti, with an unmissable view of the vineyards. Visit Castelnuovo Berardenga and the landscape museum and pass Gaiole in Chianti, the town where L’Eroica was born in 1997. You will then reach the Castello di Brolio, a symbol of Chianti and its excellent wines. Other small Chianti jewels are Villa a Sesta and San Gusmè. To conclude with a flourish, enter the historic center of Siena from Porta Romana and finish the tour in the wonderful Piazza del Campo. Dinner in a typical restaurant in the center of Siena and overnight in a 3-star hotel, located a few steps from the center of Siena. 4-star hotel available on request.

Day 5: Siena
After breakfast end of the tour and individual departure.

By choosing to travel by bike with us, you help us make the world a better place: we plant a tree for every trip sold

Why book online on Cyclando?

Because we guarantee you the lowest price and if your tour is not available or confirmed, you can always opt for the refund of the amount paid, or choose another tripfrom the over 800 on the platform.

Our cancellation insurance is the most advantageous you will find around!

Cancel for any reason

Trip cancellation for any documentable reason: pregnancy, illness, work and more, guaranteed.

Coverage of all costs

Full insurance covers all travel costs and penalties from companies, without worries.

Refund in 7 days

With Smart Claims, we guarantee fast refunds in just 7 days for complete peace of mind.

✅ What is included in the trip?

Travel/Medical Insurance 24/24
Overnight stay and breakfast
GPS or navigation APP
Luggage transfer
Local telephone assistance 7/7
Detailed description and maps of the itinerary

❌ What is not included?

Transfers not listed as "Included"
City tax
Tips
Journey to/from the starting point of the tour
Meals and drinks not listed as "Included"
Bike rental
Extras
Entrance fees, ferries and anything not listed as "Included"
Welcome briefing

💸 Cancellation fees

Time Range
Full refund
More 31 days of departure
75%
From 31 to 30 days before departure
50%
Up to 7 days before departure
Not refundable

Tuscany cycling tour from Florence to Siena

To treat yourself to an unforgettable cycling holiday in Tuscany from Florence to Siena, immersed in rolling hills and small medieval villages
To start the tour overlooking the beautiful city of Florence from the panoramic Piazzale Michelangelo
To visit Montespertoli, a pretty town located on a gentle hill in Chianti, whose surrounding countryside offers postcard landscapes
To cross Certaldo Alto, a splendid medieval village and birthplace to Boccaccio, famous medieval writer and author of the collection Decameron
To visit the enchanting Tuscan villages such as San Gimignano
To end your holiday in beauty in the splendid Piazza del Campo di Siena, considered one of the world´s greatest medieval squares and renowned worldwide for its beauty and architectural integrity
To explore Tuscany by bike and make a stop in Gaiole in Chianti, the town where the historical competition L’Eroica was born in 1997

Package only on request.

Some of our tours are not available or bookable at the moment. If you are interested in this tour, then ask our team for more information on upcoming availability, or on a similar tour available or bookable immediately!

🙋 Frequently asked questions

Can I bring my own bike?
Of course! You can participate in any tour with your own bicycle or rent one. However, we recommend renting because not all spare parts are the same, and only with our bikes can we guarantee the best mechanical assistance.
What kind of assistance will I have during the trip?
You will always have an emergency phone number to refer to. In self-guided trips, you should be able to perform minor repairs, like replacing a tube in case of a puncture, or fixing a dropped chain, but you can always count on local assistance for more serious breakdowns.
How do I know if a tour is within my capabilities?
We classify tours on a scale from 1 to 5 based on length, elevation, and complexity of the itinerary, but if you have doubts, contact us and we will help you find the most suitable journey for you.
What is the cost of renting bicycles?
The rental cost varies depending on the bicycle model and the duration of the tour. For some tours, we offer the possibility to rent different types of bicycles. During the purchase process for each route, you will be asked to indicate your preferred bike type and the corresponding price will be shown, so you can choose freely and without surprises.
Are rented bikes equipped with accessories like lights or bags?
Yes, rented bicycles are equipped with all necessary accessories to comply with road traffic regulations (lights, bell, etc.). A lock, repair kit, and a bag to carry everything you need for a day in the saddle are always included in the rental. Additionally, we offer the option to request extra accessories based on your needs.