Secrets of San Gimignano Self-Guided Cycling

9 days
Suitable for:
Age 8+
Activity level:
Activity Rating - Moderate
Trip code: 
Way to Travel:
Self-Guided Holidays
Self-Guided Cycling
Min age:

This 8-night cycling holiday combines fabulously unspoilt Chianti countryside with the chance to visit the world-famous cities of Florence and Siena. 

This holiday is, quite simply, outstanding in every way - think rich scenery, fantastically contrasting hotels, superb local cuisine and exceptional wines. 



  • Exhilarating cycling through open and totally unspoilt countryside
  • San Gimignano's soaring towers; Volterra's Etruscan treasures; great art cities of Florence, Pisa and Siena
  • Fabulous hotels all with stunning pools; superb cuisine and fine wines
  • Cypress-studded hills, sun-drenched olives, row upon row of sunflowers and world-famous vineyards
  • Pretty hamlets, hidden chapels, timeless vermilion villas

Key information

  • 8 Nights, hotel-to-hotel
  • 4 Days cycling
  • All continental breakfasts and 6 evening meals included
  • GPS route navigation provided 
  • RideWithGPS navigation app
  • High quality bikes provided
  • Luggage transfers between hotels
  • Countries visited: Italy

What's included

  • All accommodation
  • All continental breakfasts and 6 evening meals included
  • Route notes and maps provided 
  • High quality bikes provided
  • Luggage transfers between hotels

What's not included

  • Travel insurance
  • Single accommodation (available on request -compulsory supplement)
  • Visas or vaccinations
Call for general departures:
056 631 8671
Call for private group trips:
056 631 8671
Trip Notes

Click on the button below for detailed Trip Notes containing all the particulars about this trip, including kit lists and practical information.

Note: these can vary by departure; you can check out the specific Trip Notes for your chosen adventure on the dates & prices page.


Days of Cycling

The suggested cycling mainly follows quiet country lanes.

Day by day breakdown
Day 2 41.0km/26.0miles
Day 4 32.0km/20.0miles
Day 6 40.0km/25.0miles
Day 8 38.0km/24.0miles

At Exodus we believe in the power of Responsible Travel.

Every time we travel, we are part of a global movement that creates jobs, builds more sustainable societies, encourages cultural understanding and safeguards common natural and cultural heritage. To learn more about what Responsible Travel means to Exodus click here… 


  • Day 1

    Arrive in Volterra

    Arrive in Volterra where you've time for a dip in the pool and a wander round its myriad of cobbled alleys and hidden squares before dinner. (Staying at Park Hotel Le Fonti)

    Meals included: Dinner
  • Day 2

    Volterra to Pancole

    Today it's a downhill whizz out of hilltop Volterra and into the pretty Era Valley where spectacular views of the surrounding timeless Tuscan countryside open up as you pedal. After climbing out of the valley, you'll soon pass through the pretty hamlet of Castagno where we suggest a well-deserved coffee stop in the local bar. Your route continues on to Gambassi Terme, a well-preserved spa town with cobbled streets, 12th century church and lovely shaded gardens. Lunch here perhaps in one of the many trattorie then, soon after leaving the town, you'll pick up the famous Via Francigena for the gentle, mainly downhill stretch to mediaeval Certaldo where you can stop for a gelato before your final climb through olive groves and vineyards to the hamlet of Pancole. (Staying at Hotel Certaldo)


    Meals included: Breakfast
  • Day 3

    At Pancole

    If you fancy a day off from cycling, the pool here is simply gorgeous and nice lunches are served on the geranium-scented terrace. There's also a small shop where you can buy olive oils, produced by the owners, and Tuscan wines. The more energetic might want to cycle past orchards and vines to visit Boccaccio's birthplace, stunning Certaldo. Take the funicular to its medieval centre for spectacular views across the Val d'Elsa. (Staying at Hotel Certaldo)

    Meals included: Breakfast
  • Day 4

    Pancole to Colle Di Val D'Elsa

    Today's route explores the panoramic wine country between Pancole and Colle di Val d'Elsa. You'll first retrace your route to Certaldo and then follow the official, mainly off-road, Chianti Wine Route where you'll find lots of tasting opportunities - don't forget, we can collect any purchases for you! It's then on to the old town of Poggibonsi, a perfect stop for lunch and to visit the ruins of its unfinished 15th century fortress. The day ends with gentle pedalling through tree-lined meadows and a valley of poppy and sunflower fields to Colle di Val d'Elsa. (Staying at Relais Della Rovere)


    Meals included: Breakfast Dinner
  • Day 5

    At Colle Di Val D'Elsa

    There's masses of choice today: explore the mediaeval old town which dates back to Etruscan times; take the bus to Siena (30 mins) or to Florence (60 mins); take in the mediaeval town of Monteriggioni, an easy cycle or short bus ride away; or simply laze by your hotel's sparkling swimming pool, surrounded by lovely gardens. (Staying at Relais Della Rovere)

    Meals included: Breakfast Dinner
  • Day 6

    Colle Di Val D'Elsa to Pescille

     It's easy pedalling this morning as you head south past the old town of Colle di Val d'Elsa, gradually climbing up to Casole d'Elsa, a beautiful village characterised by ancient vermilion-hued buildings and blessed with stunning views from its hilltop position. Take time to explore its 12th century church (frescoes by Gano da Siena) and impressive fortress before an early lunch perhaps, in the lovely piazza. You then wind north, gently uphill, through wonderfully scenic countryside against the backdrop of the impressive mediaeval towers of San Gimignano as you pedal on to Pescille. (Staying at Hotel Pescille, Breakfast at the hotel)


    Meals included: Breakfast Dinner
  • Day 7

    At Pescille

    San Gimignano is just a short cycle away; explore its myriad of narrow streets and many hidden cobbled squares before returning to your tranquil hotel for a refreshing dip in the sparkling swimming pool. (Staying at Hotel Pescille)

    Meals included: Breakfast Dinner
  • Day 8

    Pescille to Volterra

    It's a short ride to San Gimignano today before a climb up through classic Tuscan landscapes of vines, olive groves and fields ablaze with sunflowers. Enjoy the 16km, mainly downhill run into the Era Valley. There's a real sense of achievement on your final climb through open countryside and you'll enjoy spectacular views before heading back to the ancient cobbled streets of Volterra. (Staying at Park Hotel Le Fonti)


    Meals included: Breakfast Dinner
  • Day 9

    Leave Volterra

    Meals included: Breakfast
Trip Notes

Click on the button below for detailed Trip Notes containing all the particulars about this trip, including kit lists and practical information.

Note: these can vary by departure; you can check out the specific Trip Notes for your chosen adventure on the dates & prices page.

Essential Info




There are no specific health risks.

Eating and Drinking

All continental breakfasts and 6 evening meals included

Italy’s most famous export is probably its cuisine and the traditional dishes of Tuscany are the most influential and revered. The region’s food is based on cucina povera, ‘poor/peasant cookery’, a rural cuisine based on available natural ingredients: olive oil, unsalted bread, pulses and vegetables, wild mushroom or porcini, and salt-cured meats such as salame and prosciutto. In particular, Tuscan olive oil is renowned for its quality and is the most important ingredient in the region’s cookery. You will find it in almost every dish - as a salad dressing, poured over vegetables and into soups and even as a replacement for butter on bread (very nice with a sprinkling of salt!).

Of course the Chianti region is best known for its regional wine (the very best ones are Chianti Classico and have a black cockerel stamped on the label). Chianti is produced in the vineyards dotted around the Tuscan hills; we actually visit the hills to the north of Siena, where the Chianti Colli Senesi wine is produced. Made from the Sangiovese grape, this is an excellent light, fruity red. Although best known for its red wine, a good white wine is also produced in the Chianti region. Made from the Vernaccia grape, the Vernaccia di San Gimignano is a crisp dry white which has greatly improved over recent years. It is best drunk young.


April and May departures can expect warm days and although rain is possible, it seldom lasts long. Nights may still be rather cool. We strongly recommend a fleece-lined jacket or warm sweater in these months. June sees the start of summer and July and August can become quite hot by mid afternoon, so this time is kept free for lunch. Although rain is unusual, torrential cloudbursts are not unknown. September and October are cooler and wetter, yet visibility is often better. Swimming is usually still possible at this time.

Is this trip for you?

You'll start off in Volterra, a beautifully preserved hilltop gem whose eclectic mix of Etruscan, Roman and Renaissance art and architecture has inspired artists and writers for centuries. From here, you pedal north east along quiet, rolling country lanes as you coast towards honey-coloured Pancole, nestled in the Tuscan hills. The cycling is truly glorious as you continue, via fortified towns and hill villages, to mediaeval Colle, from where you can also head to Florence and Siena for day trips. Then it's on to Pescille, which is perfectly positioned overlooking San Gimignano. Your final stretch takes you through a timeless and kaleidoscopic landscape of ochre-coloured hills and verdant vineyards, giving you a real sense of achievement as you loop back to Volterra for your final night. 

This is a self-guided cycling trip for those who like to cycle independently, but with back up to take out the hard work and planning. We arrange your accommodations, provide you with a map and route notes so that you can cycle at your own pace, while your bags are transported from one hotel to the next.
Activity Level: 2 (Leisurely/Moderate)
Please see the introductory pages of the cycling holidays brochure or our website for more important information on classification and grading.
Av. daily ride: 38km (24miles).
No. of days cycling: 4
Terrain & route: The suggested cycling is along quiet, tarmac roads (mainly traffic-free). There are a few ascents and descents along the way.

It is important that you are happy reading maps and following route notes, we make these as accurate as possible and they are regularly checked. Where possible we stick to cycle tracks and quiet roads to make the journeys as pleasant as possible, however, on occasion we have to use busier routes.

As this is a self-guided holiday there is no group and no leader. There maybe others on the same departure date as you, but you will not be organised together. The route notes contain an emergency assistance telephone number should you need it and in emergencies.

Call for general departures:
056 631 8671
Call for private group trips:
056 631 8671
Trip Notes

Click on the button below for detailed Trip Notes containing all the particulars about this trip, including kit lists and practical information.

Note: these can vary by departure; you can check out the specific Trip Notes for your chosen adventure on the dates & prices page.



Superb 3-star and 4-star contrasting hotels, all with sparkling swimming pools, are an added highlight of this holiday. In Colle di Val d'Elsa, you stay in a fabulously restored 12th century Benedictine abbey, complete with original frescoes, whilst in Volterra, your 4-star hotel has a panoramic infinity pool, with stunning, sweeping views over the Tuscan countryside. 

Call for general departures:
056 631 8671
Call for private group trips:
056 631 8671
Trip Notes

Click on the button below for detailed Trip Notes containing all the particulars about this trip, including kit lists and practical information.

Note: these can vary by departure; you can check out the specific Trip Notes for your chosen adventure on the dates & prices page.

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Dates & Prices

An overview of flight options

Exodus is committed to making joining our tours as easy as possible, wherever you live. We generally only block book seats from London, but this certainly does not mean that you need to fly from there. Depending on the route and airlines available, there will usually be various options available for those who want to fly from their local airport.

This page aims to provide a useful overview of the options available to our clients. However, the best flight arrangements should be tailored to your personal requirements, so please contact our Sales team for expert advice.


What kind of options do I have ?

1. We can book for you: Flights from anywhere in the world - not via London  

Depending on the route, this may be direct or via an overseas hub like Amsterdam, the Middle East or elsewhere. On short haul routes there may be direct flights with low cost airlines, charter flights or scheduled airlines. Exodus can book most, but not all, of these for you. The most appropriate airline may be different to that which we use for the group flight from London, but many people now travel on different airlines and meet up with their fellow passengers at the destination.

Pros  Cons
  • May be the most direct route
  • Often the extra fare compared to the London flight is minimal.
  • As you will be in the hands a single airline for your entire journey, the airline will be responsible for your bags and your connections.
  • You may not be able to join the group transfers. However, we can usually arrange private transfers, or book your flights to try and coincide with the group transfers. See notes on transfer arrangements below.


2. We can book for you: Connecting flights from your local airport to London

Exodus can book connecting flights to London so you can join the group flight there. Connecting times will be followed according to airline advice, or as requested by clients. There are two types of fares we can use for this option: a 'through-fare' or a 'published fare'.
a) A 'through-fare' is where you will be in the main airline's care throughout. You change planes, but your bags are checked all the way through to your final destination. 

b) A 'published fare' ticket is completely seperate from your onward ticket from London. It is usually cheaper than a through-fare but will need to be paid for and issued as soon as it is booked. This can be a problem if your tour has not yet reached minimum numbers. On 'published fares' neither airline is aware that you have connecting flights, so Exodus is responsible for timing your connection, not the airlines involved. The tickets are also usually non changeable and non refundable.

Pros  Cons
  • Depending on the fare type, Exodus or the airline is responsible for flight connections.
  • Through fare tickets can be expensive.
  • On a published fare, tickets must be issued immediately; tickets on published fares can be very difficult to change if onward flight times change; bags are not checked though to your final destination.
  • Published fares are non-refundable.


3. Booking some or all of the flights yourself

You can also book connecting air travel yourself, either to London, or all the way to the start point. There may be certain airlines or routes we don't have access to, so this is always an option. However, if you make your own travel arrangements you become liable for any delays, cancellations or missed connections, and Exodus is not required to offer refunds if you have trouble reaching the start of your trip.

Pros  Cons
  • You might find cheaper fares, or routes not available to Exodus.
  • You are responsible for any delays or missed connections, and the cost of the tour is not protected should you miss your flight be cancelled.


 Notes on transfer arrangements

Sometimes it is possible to travel on a different airline to the group flight from London. Where this is the case, we need to think about ensuring you meet up with the group with minimum extra cost and hassle.

  • On certain trips, it is easy to arrive on a different flight and still meet the group at the hotel with time in hand. We can usually arrange private transfers (at extra cost) or offer advice on taking a taxi to the start hotel.
  • On other trips (especially in Europe), the transfer meets the group flight and then travels some distance to the first night's accommodation. Where this is the case, our Sales team will try to arrange flights that arrive before (and depart after) the group. However, we do have to make it clear in your final documentation that if your flights are delayed, the transfer cannot wait for you. While Exodus or our local operators will do what we can to help you reach the start point of the tour, any additional costs must be paid by the client. 


Next steps? 

Call our Sales team on: 0203 733 0698

Email your query: [email protected]