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Road Cycling: Florence to Siena

5 Days & 4 Nights 5 Read 9 reviews
  • Ride the Chianti Classico wine routes of Tuscany
  • Ponte Vecchio Bridge & the Duomo of Florence
  • Cycle stages of the Giro d’Italia
  • Rustic Tuscan breads and local pomodori
  • Enjoy a Chianti in the buzz of Siena’s Piazzo del Campo
Ride from Florence to Siena through the heart of Tuscany’s Chianti postcard perfect wine region. Steeped in road cycling heritage, ride stages of the Giro d’Italia through the café filled piazza’s of Strada and Greve in Chianti. Stay at the charming Radda in Chianti, home to Tuscany’s largest collection of wine at ‘Casa del Chianti Classico’. Cycle to the towers of San Gimignano with its world class gelato. Ride Cypress tree lined roads to Siena's Piazza del Campo, perfect for people watching and a post-ride dish of local parpadelle pasta.
Graded moderate to challenging, the rolling roads of Tuscany are not to be underestimated! Each day includes several short hill climbs between 5-8km with gradients of up to 12%. Punctuated by hill top towns famed for Chianti wines and rustic regional dishes, soak up Italian life at the end of each day, staying in historic family run accommodation in the heart of Tuscany.

Tour Type:

Classic Routes | If you’re the active, outdoorsy type, who’s interested in taking on the great routes of the world or looking for a challenge, then our Classic Routes are for you. We’re talking the West Highland Way, Tour Du Mont Blanc and the Passau to Vienna Danube Cycle Path, to name but a few!


Road Biking | Road Biking

Ideal if you have an interest in:

Foodie, Wine


The cycling in this region follows well surfaced roads through towns, villages and minor country routes and is truly picture postcard Tuscany. Although the riding is not technical you must feel comfortable with rapid and sometimes narrow hairpin descents and be equipped to deal with a change in weather and road condition. Roads are often narrow and shared with cars, as such this trip is suitable only for experienced road cyclists.

Although we can supply GPX tracks along with our tried and tested detailed routes notes and maps, the roads are well signposted and are generally cycle friendly.

Should you require assistance, 24/7 telephone support will also be available throughout your trip.


Each Tuscan accommodation is different and full of character. Typical hotels and B&aB's are listed below, though on occasion we may have to book you alternative accommodation especially during the busier periods of the year. The price of your tour is based on a standard room at each of the listed accommodations.


Included are 4 breakfasts, which usually consists of fresh pastries, bread, fruits, yogurts, cheeses, meats and granola. If you have special dietary requirements do let us know at the time of booking.

Lunches and dinners are not included. Never too far from a piazza, your route notes suggest a number of local places to dine and of course, being in the heart of Chianti, there is fine red wine in abundance.

Single Rooms

If you're travelling with friends or family but prefer your own room, single rooms are subject to availability and a supplementary payment. This trip is not available to solo cyclists.

  • 2 Nights in a 4* hotel, 1 night in a 3* Hotel, and 1 night in a boutique B&B
  • 4 Breakfasts
  • Baggage transfers
  • Information pack and route notes
  • Access to detailed maps, and GPS tracks in the Macs Adventure smartphone navigation app
  • 24/7 Emergency telephone support from our office
  • Travel to Florence / from Siena
  • Bike hire
  • Lunches, dinners, drinks & snacks
  • Personal equipment
  • Travel insurance (required)
  • Additional nights along the route
  • Hire of a high quality road bike
  • Arrival / departure transfers

When To Go

This trip is available to start on any day from May to October and we suggest that you contact us as soon as possible if you are considering a departure during the peak season of May-June and September.

Please bear in mind that July and August can be hot for cycling. It is advised to always carry plenty of water (to stay hydrated), wear sunscreen and protective clothing such as a sunhat. It is also recommended to avoid cycling at noon on very hot days, this can be avoided by starting early!

Getting to the Start

Florence Airport is served by a limited number of scheduled and low-cost airlines and is approximately a 20 minute bus or taxi journey to Florence Central Station. 

Alternatively Pisa Airport is just over a 60 minute train journey from Florence. From the airport a ten-minute connecting bus service will take you from the airport to Pisa Central station. From here hourly services run through to Florence.

Rome Fiumicino airport train station also connects with Florence via an approximate 2.5hr journey time.

Information on train journey times and booking, tickets can be accessed at  The Trainline Europe.

Getting from the End

Siena does not have an airport but is on a main train line and has a number of daily services to the following cities:

Pisa, 1hr 45min journey time. Daily services, up to 2 per hour.

Florence, 1-2 hours journey time. Daily services, up to 2 per hour.

Rome, 3.5 hours journey time. Daily services up to 5-6 per hour.

For more information on train times and tickets The Trainline Europe.

Luggage Transfer

Baggage transfers are included in the price of your trip. We ask you to keep your baggage to a maximum of 1 bag per person (maximum weight 20 kg). If you require excess baggage allowance do contact us prior to travel.

General Information

All bike tours are unescorted. The distances listed are approximations of the recommended routes. Please be prepared by packing all necessary items, for example, cycle clothing and personal medications etc.


We recognise the importance of being at one with your bike, which is why we have partnered with a preferred road bike supplier in Tuscany.

Focus Cayo 5.0 carbon bikes are available to hire in a number of sizes. All bikes come with a spare tube, pump, levers and a cycle computer. Your hire bike will be delivered to your hotel in Florence and can be set up with flat, Look or Shimano spd pedals. If you’d like to hire a bike, please let us know your height and frame size you currently ride, along with any other specific requests you may have. We’re always happy to answer any questions regarding hire bikes.

If you would like to bring your own road bike please ensure it is thoroughly serviced and is an appropriate road bike for this trip.

Travel Insurance

It is a requirement of booking this tour with Macs Bike that you have suitable Travel Insurance which covers you for the activity, emergency evacuation and hospital care.

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Day 1 Arrive Florence Day 2 Cycle to Radda in Chianti 35 miles / 55 km Day 3 Chianti Winelands Loop Ride 35 miles / 55 km Day 4 Cycle to Siena 48 miles / 76 km Day 5 Onward Travel

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