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Cycling Tuscany: Chianti & Siena

8 Days & 7 Nights 4.5 Read 13 reviews
  • Cycle the rolling Cypress tree lined Tuscan hills
  • Dine in the buzz of Piazza di Campo, Siena
  • Ride amongst the vineyards of Montepulciano
  • Poolside relaxtion 'Under a Tuscan Sun'
  • Sample the gelato of San Gimignano
Experience the very best of classic Tuscany on a self-guided cycle tour. Take to two wheels and cycle bella Italia, discovering picture-postcard Medieval and Renaissance hill-top villages, accompanied by sumptuous cuisine and the famed Chianti, Brunello and Nobile wines. Each day you will be cycling at your leisure through impossibly pretty scenery, characterised at first by vineyards and verdant farmland which lead to contrasting cypress-lined country roads, the UNESCO World Heritage Landscape-listed Val d’Orcadia and the grey hues of the ‘Crete’ region. Your Tuscan adventure starts with an incredible first day’s cycling; visit the fortified town of Monteriggioni, before heading to one of Italy’s most spell-binding locations—San Gimignano with its many towers. Each day you’ll reach traditional villages perched atop rolling hills filled with stunning red brick and earthen-coloured buildings, with roofs baked by the Tuscan sun. Highlights include magical Siena, the thermal-spa town of Bagno Vignoni and Pienza, as well as photogenic Montichiello and Montepulciano. Cool churches, abbeys and monasteries await you, where Gregorian chants drift through the air and create a special ambience. Take time to reflect at the Monte Oliveto monastery and peaceful abbey of Sant’ Antimo. You’ll also pass through towns located on the route of the ancient Via Francigena pilgrimage. And the end to each perfect day’s cycling? You’ll certainly have earned a glass or two of full-bodied Italian red accompanied by a dish garnished with local pecorino cheese and truffles! Tuscany is well known for its steep hills and therefore this trip will appeal to those with a good level of fitness, with daily distances ranging from 35 to 46 kilometres.
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What To Expect

Indulge in the very best of classic Tuscany on two wheels, enjoying fantastic wine and authentic cuisine. This trip requires a good level of fitness and offers cyclists a taste of the delights of Tuscany, with its fascinating abbeys, Renaissance towns and delicious food, whilst burning off any extra holiday calories!

Trip Style:

Self Guided | Go at your own pace on an independent holiday.


Inn to Inn Cycling | A classic point to point cycling holiday, staying in a different location each night

This trip is suitable for:

Solo Travellers

Ideal if you have an interest in:

  • Foodie Adventures
  • Wine, Whisky & More...
  • Historical Journeys


  • Most Popular
  • Classic

Grade & Terrain

This cycling tour is graded easy to moderate depending on the choice of route. Each day you can choose the difficulty, with the longer/steeper routes requiring a reasonable level of fitness. The routes follow surfaced country roads and secondary roads. Near larger towns there are some sections on busier.


Our tried and tested route notes together with easy to follow maps are supplied, meaning you should have no problems finding the way.

Accommodation Information

Overnight in charming hotels, one countryside agriturisimo and a B&B. All properties are chosen for their excellent location, charm, warm welcome to cyclists and spectacular views. Some hotels also have swimming pools.

We always try and accommodate you at the locations detailed below, but on occassion, we may have use an alternate accommodation of equal or higher standard.

Single Rooms & Solo Cyclists

If you're travelling with family or friends but prefer your own room, it's possible to request a single room. This trip is suitable for solo travellers although there is a solo supplement payable.


The delicious Tuscan food and wine is undoubtedly a highlight of this holiday. The holiday includes two dinners (one at Villa San Lucchese and one at Pieve a Salti), and breakfast each morning.  Lunches and dinners (excluding aforementioned) are not included so you are free to choose and will be available at your hotel or nearby restaurants.

  • 7 Nights in hand-picked accommodations
  • 7 Breakfasts
  • 2 Dinners (at Villa San Lucchese and Pieve a Salti)
  • Baggage transfers
  • Transfer on day 8 from Montepulciano to Chiusi
  • Welcome briefing and bike hire fitting (if hiring a bike)
  • Information pack and route notes with maps
  • 24/7 Emergency telephone support from our office
  • Travel to Poggibonsi / from Chiusi
  • Bike hire (standard hybrid or upgrade to a road bike)
  • 5 Dinners
  • Lunches, drinks & snacks
  • Entrance fees for attractions
  • Travel insurance (required)
  • Additional nights along the route
  • Bike hire (standard 27 gear hybrid)
  • Upgrade to a road bike

When To Go

You can begin on any day of the week from March to early November. Spring, early summer and autumn days are the perfect temperature for cycling and capturing the essence of Tuscany's colourful landscapes. During the hotter summer months it's worth hitting the road earlier in the day, or reconsidering dates if you don't enjoy the heat.

Getting to the Start

By Air:  We recommend flying to Florence or Pisa airport.

By train:  You can take a train from Florence or Pisa to the start of the - Poggibonsi (1hr and 1h16 respectively). For train timetables visit Tren Italia

Getting from the End

At the end of your holiday we include a transfer to Chiusi train station.

By Air:  From Chuisi you can take a train to Florence (1h 26) and then either a bus or a taxi to Florence Airport. If flying out of Pisa then take a train from Chiusi (2h 40, changing in Florence).

Baggage Transfer

Your bags will be collected from your accommodation each day and moved onto your overnight accommodation. We ask you to limit your luggage to one bag of up to 20kg per person.


Your information pack has a detailed equipment list with essential kit and handy suggestions.  

Bike Hire

Bike hire is available as an optional extra. Choose from a Hybrid bike (Shimano Alivio 27-gear with 13 kg aluminium frame), or a road bike (Bianchi Via Nirone with Shimano Sora 27-gears). Bikes are equipped with rear rack, 1 rear pannier, odometer, pump, repair kit, water bottle and map folder. If you opt for bike hire we will ask for your height to make sure your bike is the perfect fit. A welcome meeting and a bike fitting will be on your first evening.

Travel Insurance

It is a requirement of booking this tour with Macs Adventure that you have suitable travel insurance which covers you for the activity and emergency evacuation and hospital care.

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Day 1 Arrive Poggibonsi and overnight Day 2 Loop cycle to Monteriggioni, Colle Val d’Elsa and San Gimignano 22 miles / 35 km Day 3 Poggibonsi to Siena 25 miles / 40 km Day 4 Siena to ‘Crete’ to Buonconvento 25 miles / 39 km Day 5 Cycle to Monte Oliveto Monastery and Montalcino 29 miles / 46 km Day 6 Loop cycle to Sant’ Antimo Abbey 20 miles / 32 km Day 7 Cycle to Pienza, Montichiello and Montepulciano 28 miles / 45 km Day 8 Onward travel

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