Tour of Tuscany: Florence to Montepulciano

8 Days & 7 Nights 5 Read 4 reviews
  • Cycle Tuscany’s classic hills of Chianti & Montepulciano
  • Visit the Ponte Vecchio Bridge of Florence
  • Ride historic stages of Giro d’Italia
  • Relax with a Chianti in Siena’s Piazza del Campo
  • Cycle the UNESCO Val d'Orica region
Take on our Tour of Tuscany cycling from Florence, through the world-class winelands of Chianti and Montepulciano. Ride the rolling Chiantigiana to Radda in Chianti and Tuscany’s largest collection of wine, ‘Casa del Chianti’. Follow stages of Giro d’Italia to the towers of San Gimignano and the buzz of Siena’s Piazza del Campo (perfect for a post-ride vino rosso!). Ride the exquisite Val d’Orica and round off your tour with a glass of the reputed Vino di Nobile in medieval Montepulciano.
This road cycling tour is graded moderate to challenging. Tuscany is well known for its rolling roads and is a firm favourite with the pro's. Each day ride includes hill climbs between 5-8km with gradients of up to 12% in places. At the end of each ride soak up Italian life in the buzz of a piazza with rustic regional dishes and a large glass of Chianti or Montepulciano!

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!


Leisure Cycling | Leisure Cycling

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. Make sure to always be mindful of other road users, especially on roads shared with traffic. 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 conditions.

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 B&B's and hotels are listed below, though on occasion we may have to book you alternative accommodation especially during the busier periods of the year. We always book an equal or better alternative hotel or bed and breakfast.


Included are 4 breakfasts, which usually consist of fresh pastries, breads, 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 and Montepulciano, 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.

  • 3 Nights in B&B's and guesthouses and 4 nights in 3* Hotel
  • 7 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 Siena / from Montepulciano
  • Road bike hire
  • Lunches, dinners, drinks & snacks
  • Personal equipment
  • Travel insurance (required)
  • Additional nights along the route
  • Road bike hire

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.

July and August are the hottest months with little to no rainfall. The temperatures rise into the 30-degree celsius during the day. The months before and after the high season will be sunny but a little cooler, which could be preferable when cycling. Always make sure to stay hydrated, take plenty of water and wear sunscreen and a sunhat.

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

Montepulciano does not have an airport but is only a 20 minute drive from Chiusi Train Sation which has connections to the following cities. We can easily arrange a short transfer to Chiusi train station if required.

Pisa, 3hrs journey time. Daily services, up to 1 per hour.

Florence, 1.5-2 hours journey time. Daily services, up to 1 per hour.

Rome, 1.5-2 hours journey time. Daily services up to 1 per hour.

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

Luggage Transfer

Your bags will be transferred between your accommodation as per your itinerary. We ask you to limit your luggage to one bag of up to 20kg per person.

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 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 Siena and The Montagnola Region 36 miles / 57 km Day 6 Siena to Montepulciano 38 miles / 60 km Day 7 Montepulciano 50 miles / 80 km Day 8 Onward Travel

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