Discover the beauty of the region between Florence Siena and the Chianti

Tuscany is one of the better known and fascinating regions of Italy, so would you like to join us in this amazing Cycling Chianti Bike Tour ?


Piazza del Campo in Siena, home of the historical Palio race

The Chianti hillsides, offering an unique landscape

Cantucci and Ricciarelli, typical biscuits of Siena

Brunello di Montalcino, red wine

Bistecca alla Fiorentina, a large grilled beef T-bone steak

Tuscany is one of the better known and fascinating regions of Italy. It was here that Michelangelo and Leonardo da Vinci created their best works of art. The countless palazzos, triumphal arches, mosaics and frescoes now serve as signposts for the cycle route taking you into the breath-taking beauty of Florence, Siena and San Gimignano.

You’ll have the chance to visit the superb medieval town of Siena, as well as to admire Florence, the cradle of Renaissance. Last but not least, in this tour you’ll discover also picturesque villages where you’ll be tempted by the excellent Tuscan cuisine.

Well now you can experience as many of these Italian cycling highlights as you would like in one holiday. Cycling guides, routes, bike rentals, transfers… We will organize everything. All you need to think about is just book this fantastic cycling holiday.

Enjoy a memorable Tour rich in History and Amazing Landscape

Cycling Chianti Bike Tour

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Day by Day Itinerary
1. Siena.

Individual arrival.

2. Siena–Radda in Chianti

(45 km, elevation up 900 m).

From Siena you start to head north towards the beautiful village of Radda in Chianti. The remains of its ancient walls show the historical significance that this town had in the competition between Florence and Siena.

3. Radda in Chianti–Greve

(40 km, elevation up 500 m).

The route brings you to Greve over the rounded hills with beautiful views.

4. Greve–Florence

(40 km, elevation up 600 m).

Florence, capital of the region of Tuscany, spreads on the banks of the Arno, between the Adriatic and the Tyrrhenian seas, almost in the middle of the Italian peninsula. Two of the many artists associated with Florence are Leonardo da Vinci and Michelangelo Buonarroti. The city considered the birthplace of the Italian Renaissance, it was long ruled by the Medici family, has a huge Cultural Heritage. See our list of tours available to discover the treasures of the city !

5. Florence – Tavarnelle

(40 km, elevation up 378 m).

The village of Tavarnelle Val di Pesa has Roman origins; it is named after the ancient taverns offering accommodation and refreshment located along the road which linked Florence to Siena and thence to Rome./p>

6. Tavarnelle – Colle Val d’Elsa

(40 km, elevation up 141 m).

From Tavarnelle you cycle to Colle Val d’Elsa, which lies in the heart of Tuscany, in a strategically favourable position near the towns of Siena and Florence. It is situated on the via Francigena that connects Rome with the North. On the way you pass Certaldo, birthplace of Boccaccio, whose upper part has remained as it was in the Middle Ages. Further on you come across San Gimignano, which rises on a hill dominating the Val d’Elsa with its towers.

7. Colle Val D’Elsa–Siena

(40 km, elevation 322 m).

From Colle Val d’Elsa you will cycle to the beautiful town of Siena, which is not only one of the most fascinating towns in Tuscany but is also in a particularly beautiful position, with lovely surroundings, and traditional sweets.

8. Siena

Departure after breakfast

Due to organisational reasons, weather conditions or provisions issued by local authorities, the itinerary may be subject to some changes before and/or during the holiday.

Along the way you may find temporary deviations (for example road works) which cannot be foreseen; in this case each rider can decide autonomously how to deal with these stretches.

Route Profile
  • Total Length: 250 km
  • Total vertical up: 3,970 m
  • Terrain: 95% tarmac, 5% unpaved
  • Train connection among the overnight stays: NO
  • Possibility to shorten the itinerary by taking the train: NO

Heavy, with sloping landscapes dotted with steeper inclines, but not overwhelmingly so. The daily distance is about 40 kilometres. Though the daily routes are not too long, they can be strenuous, so we do recommend being in reasonably good physical condition for this tour.

Moderate: hilly areas, numerous climbs and downhill stretches. Suitable for regular cyclists with a good level of fitness.

How to Get There
By Plane

Siena is connected with the following airports: Florence (FLR) 85 Km, Pisa (PSA) 150 Km.


For further information on timetables and prices you can consult the following website:
Accommodation and Meals

We personally choose all the hotels mindful of your comfort as well as the proximity to cycling paths and any relevant local sites. The hotels of this tour are:

Category A: 3* hotels (in Colle val d’Elsa sometimes a cosy BB).

All rooms have en suite facilities; some accommodation facilities may be without air conditioning.

Price includes 7 nights hotel accommodation with breakfast buffet.

When you book the tour please specify the type of room requested:

  • double room is a room with one double bed
  • twin room is a room with two single beds
  • triple room is usually a room with one double bed and a single bed or a rollaway.
Bikes & Accessories

At the moment of booking, you can choose among the following bikes:

  • City bike 27-gear Shimano Deore
  • Electro-bike 8-gear Shimano Nexus


  • aluminium frame
  • mudguard
  • rear rack
  • comfort gel saddle
  • anti-puncture Schwalbe tyres
  • ergonomic bicycle grips
  • Speed Lifter system (only for City bikes)


  • 1 cycle computer
  • 1 Ortlieb one-sided saddlebag
  • 1 front bar bag or 1 map holder
  • 1 water bottle (0.75 l)
  • 1 repair kit per room (which includes 1 spare inner tube, glue, patch, a pump, 2 allen keys and tyre levers)
  • 1 combination bike lock

At the moment of booking you can also rent helmets, suitable for head circumferences from 54 to 61. All helmets have a certification mark according to the DIN EN 1078 (CE) European norm.

Accompanying Material

The Information Pack (one per room) includes:

  • roadbook describing the cycling route stage by stage
  • bike maps
  • Our Greens Cycling Guide
  • final hotel list: due to overbooking or organisational needs your hotel list may be changed just before your arrival
  • luggage labels to be fixed at each piece of baggage, which has to be carried
  • hotel vouchers to be given to the reception of each hotel on your arrival.
By Your Side

In case of an emergency and also in case of a technical problem with your rented bike you can contact our cell phone number (everyday 8:00-20:00).

The number will be specified in the Final Tour Details.

How to Book the Tour

Send us your booking: within this time and a copy of the deposit (25% of the total amount of the tour price). You can pay per credit card or per bank transfer on our account.

We will send you the booking confirmation : after receiving the deposit.

Send us the balance 30 days before the departure.

Receive the travel documents: after the payment we will send you the hotel list and the general travel information per e-mail. The travel documents will be sent by post (EU countries) or delivered on site.

Other Tours to combine with

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Bikes & Accessories

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Cycling Chianti Bike Tour

8D/7N – 3* Hotels & B/B
  • TOUR TYPE: Self-Guided
  • DEPARTURES 2017: 
  • SA from 8.04 to 7.10.2017
    Special departure dates for at least 5 pax
  • Season 1: 8.04 – 5.05 and 24.09 – 7.10.2017
    Season 2: 6.05 – 23.09.2017
  • 590 € in double room, 3* Hotels, B&B
  • + 7-nights Hotel accommodation
  • + Breakfast Buffet
  • + Luggage transportation
  • + Route descriptions & Maps
  • + 7-days Hotline service
  • – Local taxes: (approx. 10-15 €)
  • – Everything not mentioned in the section “Included”
  • 200 € Single room
    60 € Season 2
    170 € Half board, 6 dinners included (3 course-meals, beverages not included)
    70 € Bike Rental
    170 € E-Bike Rental
    15 € Helmet
Extra nights in double/single room with breakfast:
60/90 € in Siena
from 75/130 € in Florence
    100 € 3rd person in room
Tour Code TH0057

from 590 € – Book Now

Cycling Chianti Bike Tour

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Cycling Chianti Bike Tour - Map of the Itinerary

Map of the Itinerary


Some notes on the Chianti Region


A Glass of Chianti

The Chianti region is one of the most beautiful and famous areas in Tuscany. Chianti is strongly tied to its wine and its wine culture. Chianti’s gentle hills are alluringly sketched by miles and miles of vineyards that each season color the landscape in different hues. Hills in shades of green, purple, red and yellow attract thousands of visitors every year.

Chianti (pronounced [ˈkjanti]) is a red Italian wine produced in Tuscany. It was historically associated with a squat bottle enclosed in a straw basket, called a fiasco (“flask”; pl. fiaschi); however, the fiasco is only used by a few makers of the wine now; most Chianti is now bottled in more standard shaped wine bottles. Baron Bettino Ricasoli (later Prime Minister in the Kingdom of Italy) created the Chianti recipe of 70% Sangiovese, 15% Canaiolo and 15% Malvasia bianca in the middle of the nineteenth century.


Map of Chianti

The first definition of a wine-area called Chianti was made in 1716. It described the area near the villages of Gaiole, Castellina and Radda; the so-called Lega del Chianti and later Provincia del Chianti (Chianti province). In 1932 the Chianti area was completely re-drawn and divided in seven sub-areas: Classico, Colli Aretini, Colli Fiorentini, Colline Pisane, Colli Senesi, Montalbano and Rùfina. Most of the villages that in 1932 were suddenly included in the new Chianti Classico area added in Chianti to their name-such as Greve in Chianti which amended its name in 1972. Wines labeled Chianti Classico come from the biggest sub-area of Chianti, that sub-area that includes the old Chianti area. 

Chianti Classico

In 1716 Cosimo III de’ Medici, Grand Duke of Tuscany issued an edict legislating that the three villages of the Lega del Chianti (Castellina in Chianti, Gaiole in Chianti, and Radda in Chianti) as well as the village of Greve and a 2-mile (3-km) stretch of hillside north of Greve near Spedaluzza as the only officially recognized producers of Chianti. This delineation existed until July 1932, when the Italian government expanded the Chianti zone to include the outlying areas of Castellina in ChiantiGaiole in ChiantiGreve in ChiantiRadda in Chianti,  and part of territories of Barberino Val d’ElsaSan Casciano in Val di Pesa and Tavarnelle Val di Pesa, in the province of Florence, and Castelnuovo Berardenga, Poggibonsi in the province of Siena.

Black Rooster

I Love Bike Holidays

I Love Bike Holidays

The black rooster (gallo nero in Italian) that appears on the neck labels of many Chianti Classico is the symbol of the Consorzio Chianti Classico, the foundation of producers in the Chianti Classico region. The foundation was founded with the aim of promoting the wines of the region, improving quality and preventing wine fraud. Since the 1980s, the foundation has sponsored extensive research into the viticultural and winemaking practice of the Chianti Classic area, particularly in the area of clonal research. In the last quarter of a century more than 50% of the vineyards in the Chianti Classic region have been replanted with improved Sangiovese clones and to modern vineyard schematics as part of the Consorzio Chianti Classico’s project “Chianti 2000”.

To Combine with



Bike & Hotel



Following the River Arno Between Pisa and Florence

8D/7N – 2/3/4* hotels

from 640 €

Click on the image to see full details

Our Bikes

Our bikes

Tough, stable and reliable, specially designed for you to saddle up for several days on the trot. Our bikes are citybikes with an aluminium frame and kitted with responsive brakes and gears. Plus: mudguards, trip computers, comfort gel saddles, flat-palmed grips, Schwalbe Marathon anti-puncture tyres. Where we don’t transport our own bikes, they are supplied by our trusted local partners.

E-bikes are also available for most of our tours, while kids’ bikes and accessories are at hand for all family-friendly holidays.

27-gear unisex City Sports Bike

27-gear unisex City Sports Bike

27-gear unisex City Sports Bike

A low entry unisex frame, ideal for an upright but relaxed riding position. The number of gears varies by destination.

In Italy, for instance, standard bikes have 21/24 gears, while in northern Europe they are generally fitted with 7 gears and a pedal brake (although bikes with more gears and conventional breaks can sometimes be requested).


27-gear Men’s City Sports Bike

27-gear Men’s City Sports Bike

Citybike with men’s frame. The design and number of gears varies from country to country.

As with unisex bikes, for example, bikes for our Italian tours have 21/24 gears, while in northern Europe they are usually fitted with 7 gears and a pedal brake (although bikes with more gears and conventional breaks can sometimes be requested).



Electro bike

Comfortable and easy to get to grips with, ideal for anyone who thinks they might need that extra push or just wants to take it in their stride.

Our e-bikes are fitted with a BionX kit and the motor at the rear.

Where we don’t transport our own bikes, they are supplied by our local partners.




With carbon fork and 27-gear Shimano Tiagra

TYRES: Vittoria

GEAR: Shimano Tiagra 27 gears

FORK: carbon

DESTINATION: Veneto, Trentino-Alto Adige, Lombardy



Standard Tandem

The standard tandem comes with 8 gears

26” wheels

Shimano V-brakes and weighs 18kg.

Tandem Hasebike

Tandem Hasebike

Tandem Hasebike

One recumbent seat at the front, one saddle at the back

The front seat would suit a range of cyclists with disabilities or balance problems.


Fully Equipped 

These vary by destination and local supplier. The trip dossier you receive before your holiday will list all relevant accessories, and you can simply request them locally (rather than ahead of the tour).

Repair Kit

Repair Kit

Repair Kit

For every booking you receive a reparation Kit (1 every two bicycles) with the necessary equipment to adjust the handlebar and to replace the tube in case of puncture.

The kit includes:

  • 1 Pump
  • 1 Tube
  • 2 Allen keys
  • Tyre levers
  • patches and mastic sealant

Klickfix Handlebag

Klickfix Handlebag

Klickfix Handlebag

Waterproof rigid handlebar bag with a readily-accessible main compartment:

  • with CLIC-fix handlebar adapter
  • Norco Tarpulin waterproof fabric 3D-welded
  • Waterproof double-sided maps envelope
  • Large top lid for easy access
  • Reflective logo and shoulder strap
  • Dimensionally stable internal plastic frame
  • Inside pocket with key ring
  • Volume: 7,0 Liter
  • weight: 770 g

Comfortable Saddle

Comfortable Saddle

Comfortable Saddle

The producing company Selle Royal, world leader in the bike saddle sector, supplies all the saddles for the bikes on our tours.

Bike Helmet

Bike Helmet

Bike Helmet

In-mould, lightweight, strong and versatile model for everyday riding.

The new adjustable size system and the cool pads for an excellent fit and comfort.

  • 10 vents with bug net for a great airflow
  • Removable visor
  • Certified CE (TÜV) and CPSC-USA.

Bike Basket

Bike Basket

Bike Basket

Large volume, meshed, oval-shaped basket. Comfortable integrated handle with a catch at 90°.

  • Material: alluminum
  • Dimensions: 36×27×25 cm (HxWxD)
  • Weight: 1.250 g
  • Capacity: 18 l, 7 kg


Bike Map Holder

Bike Map Holder

Bike Map Holder

Lightweight, full-size map holder for every common map format. Its horizontal position minimizes the impact of wind. The removable, transparent hood protects the map from dirt and rain. Sunny automatically locks into the handlebar adapter.

Material: plastic – Dimensions: 27×27 cm (HxW)

Weight: 260 g