Current as of: July 24, 2024 - 00:42

Secrets of San Gimignano Cycling

Secrets of San Gimignano Cycling Trip Notes

  • Ways to Travel: Self-Guided Holidays
  • Destination: Italy
  • Programmes: Cycling
  • Activity Level:

    3 out of 7 - Moderate

  • 9 Days: Flight Inclusive
  • 9 Days: Land Only
  • Ages: 18+
  • Trip Code: C08TY

Trip Overview

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

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’ll pedal through the archetypal Tuscan countryside, cypress dotted rolling hills, olives, vines, sunflowers, and on, via postcard-pretty Certaldo. The cycling is truly glorious as you continue, via fortified towns and hill villages, to medieval Colle di Val d’Elsa, 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.


At a Glance

  • 8 Nights, hotel-to-hotel
  • 4 Days cycling
  • E-bike hire available on request (supplement applies)
  • Management by your Headwater appointed agent


  • 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

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.


As this is a self-guided holiday there is no group and no leader. Your luggage is transferred and route notes and maps are provided. Please note: the walking and luggage transfers included in this tour are subject to a minimum of 2 people (in total) booked on the departure. A supplement (payable in advance) to cover these transfers and sole occupancy of a room will apply if only 1 person travelling on a departure date.

Adult min age: 18


Secrets of San Gimignano Cycling

Land Only

  • Start City: Volterra
  • End City: Volterra

Flight Inclusive

  • Start City: London
  • End City: London

Land Only Itinerary

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.
You stay at Hotel San Lino (breakfast included)

Meals included: Dinner

Day 2
Volterra to Certaldo

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 medieval Certaldo where you stay for the next two nights.
You stay at Hotel Certaldo (breakfast included)


Distance covered: 25mi (41km)

Meals included: Breakfast

Day 3
At Certaldo

Explore stunning Certaldo, Boccaccio’s birthplace. Split into two distinct halves, the medieval centre of Certaldo Alto with its fabulous ancient buildings, is accessed by funicular and offers spectacular views across the Val d’Elsa. On the other hand, Certaldo Basso is the more modern part of the town with shops, bars and restaurants. You could also spend time today, relaxing by the hotel pool.
You stay at the Hotel Certaldo (breakfast included)

Meals included: Breakfast

Day 4
Certaldo to Colle di Val D'Elsa

Today’s route explores the panoramic wine country between Certaldo 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! 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.
You stay at Palazzo San Lorenzo (breakfast and evening meal)


Distance covered: 20mi (32km)

Meals included: Breakfast, Dinner

Day 5
At Colle di Val D'Elsa

There’s masses of choice today: explore the medieval old town which dates back to Etruscan times; take the bus to Siena (30 mins) or to Florence (60 mins); take in the medieval town of Monteriggioni, an easy cycle or short bus ride away; or simply enjoy the spa facilities of your **** hotel.
You stay at Palazzo San Lorenzo (breakfast and evening meal)

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 medieval towers of San Gimignano as you pedal on to Pescille.
You stay at Hotel Pescille (breakfast at the hotel, evening meal at a local restaurant)


Distance covered: 25mi (40km)

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.
You stay at Hotel Pescille (breakfast at the hotel, evening meal at a local restaurant)

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.
You stay at Hotel San Lino (breakfast included)


Distance covered: 24mi (38km)

Meals included: Breakfast

Day 9
Leave Volterra

The tour ends in Volterra.

Meals included: Breakfast

Ascents, descents and distances: All ascents, descents and distances listed in the daily itinerary have been measured by our local partners or tour leaders, in many cases with satellite-based mapping software. However, different GPS measuring devices can give differing results, particularly on winding paths or in mountainous terrain. Measurements stated throughout these Trips Notes are given to help you understand the types of terrain and distances you will encounter. Timings stated will vary depending on the pace of your group.



Secrets of San Gimignano Cycling

Superb 3-star and 4-star contrasting hotels. 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.

Single supplement from £ 558

Food & Drink

All continental breakfasts and 4 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.

Weather & Seasonality

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.

Weather Charts

Secrets of San Gimignano Cycling

Joining Instructions

The tour itself normally begins at the start hotel in Volterra on the afternoon of Day 1 of the itinerary.

We can also book flights for you. The standard flights we usually use are with British Airways Heathrow to Pisa 08:25/11:35 transfer to hotel 75 minutes. Return: Transfer to airport 75 minutes British Airways Pisa to Heathrow 12:35/14:00 Business/club/first class seats are available on request.Please note that the standard flights/trains may occasionally change throughout the season so please enquire for up-to-date details.

Full joining instructions including local emergency numbers will be sent to you as part of our Final Joining Instructions. If you do not receive these at least a week before departure, or require them earlier please contact our office or your travel agent.

Location start: Volterra
Location end: Volterra

Transfer Details

Standard transfers
For flight inclusive bookings transfers included from Pisa airport at 11:35, and back to Pisa airport at 09:00.  For land only bookings transfers are available at a supplement.

Alternative transfers
If you require alternative transfers (because you will be arriving at a different time to our standard flights), then we can usually arrange these for you (there may be an additional charge).

What To Take

Essential Equipment


Warm jumper/fleece


Water bottle (1 litre) you will be able to refill each day at the accommodation.

Optional Equipment

Torch (useful for walking to the village in the evening)


GPS Route Navigation

Ride with GPS logo

We’ve teamed up with RideWithGPS to provide our carefully researched and checked itineraries in a convenient format, similar to a car satnav, with turn-by-turn instructions all along your route.

Before you travel we’ll send you everything you need to download your route notes and the free RideWithGPS app. It’s available for iPhone and Android and the routes can also be used on any regular GPS device such as the Garmin Edge bike computers or Forerunner fitness devices.

For more details and to watch the demonstration video, please visit our GPS Route Navigation page.

If you prefer the familiarity of your own bike, you may, of course, bring it along. Please advise us at the time of booking and you will receive a discount on the price of the holiday, as specified above. You will be responsible for any extra baggage charges, please speak to your sales representative for individual airline fees. Please note, this does not apply to trips within the UK, for which local bike hire is not included.

You will also be responsible for assembling and disassembling your bike as well as bringing along spare parts and any tools specific to it. It is also your responsibility to ensure your bike is roadworthy and suitable for the type of cycling undertaken. If in doubt, the model of local bike hire available should act as a guide and details of terrain, ascent and descent are available both in the itinerary and in the ‘Is this trip for you?’ sections. Our cycling team only carry the relevant spares for the hire fleet. Any clients bringing their own bike should ensure they have adequate cover for loss, damage or theft under their travel, home contents or a specialist insurance policy. If Exodus is confident we have taken all reasonable care to ensure the safety of your bike, in the rare event of loss, damage or theft, you will need to claim under your own insurance policy.

Extra bike accessories

You may like to bring your own pedals and saddle (excluding the seat post) or gel saddle cover to fit to the hire bikes. We encourage this, if it is your preference. However, please note that you are responsible for your own equipment, and removing your saddle/pedals at the end of the trip. We cannot guarantee the return of any bike parts left behind.

Recommended Cycling Clothing

Padded cycling shorts (with loose ‘over-shorts’ where recommended), breathable clothing, and a lightweight waterproof/windproof top. Shoes with relatively stiff soles are better for biking, but are not essential unless you are cycling long distances. Most people want to carry certain items with them during the day while cycling, for this we recommend a large bum bag (fanny pack) or small close-fitting daysack.

Exodus Policy on Cycling Helmets

Wearing a helmet is mandatory for anyone taking part in any guided Exodus cycling holiday. Group members must bring their own helmets, as they are not available for hire, even if they are hiring a bike from Exodus.

For self-guided cycling holidays wearing a helmet is highly recommended. Customers who choose to ignore our advice do so entirely at their own risk and on the understanding that it may affect the validity of their travel insurance. It should also be noted that in some countries, wearing a helmet is a legal requirement.

Cycling of all kinds has its dangers and accidents can happen from time to time. Please ensure that you are properly prepared for the riding you are going to undertake.

Local Bike Details

A quality local hire bike is included in the overall price of our cycling holidays. At the time of booking we will take your height in order to reserve equipment. There may on occasions be insufficient bikes available in the correct size; we will endeavour to find suitable alternative equipment but this cannot be guaranteed. We will tell you before you book whether suitably sized bikes are available.


1. The equipment remains the property of the supplier and you may not sell, hire out or part possession with the equipment.
2. You must not misuse the equipment and must return it in the same condition as when received (ordinary wear and tear excepted). The supplier is entitled to charge for any damage caused to the equipment during the period of hire.
3. You must ensure that the equipment is adequately secured when not in use. In the event of the equipment being lost or stolen, you may be liable for the replacement value of the equipment
4. You must not use the equipment whilst under the influence of drink or drugs and should immediately notify the Supplier in the event of breakdown or loss.

Reading List

  • The Rough Guide to Tuscany and Umbria
  • Lonely Planet Tuscany and Umbria
  • DK Eyewitness Travel Guide: Florence and Tuscany
  • Time Out Florence: And the Best of Tuscany


Practical Information



Travellers from the UK, US and EU normally do not need a visa to enter Italy. Please note, visa requirements often change and it is your responsibility to obtain any required visas for this trip. Therefore, we recommend that you check with the nearest embassy or consulate of your chosen destination(s), including any countries you may be transiting or transferring through.

Some local governments provide guidance on what visas their citizens need. To help, we’ve gathered a selection of useful links below.

• Australia:
• Canada:
• United Kingdom:
• USA:

Please note: it is compulsory to carry ID with you at all times in Italy.

Vaccinations and Health


There are no required vaccinations. However, you may want to consider vaccinations for tetanus, rabies and tick-borne encephalitis. Please confirm with your doctor or travel clinic.

Local Time

Italy's time zone: Europe/Rome (UTC +02:00)


Italy's electricity: Plug types C (two round pins, European standard), F (two round pins), and L (three round pins in a row) – 230V, 50Hz

Secrets of San Gimignano Cycling


Italy's currency: Euros (EUR)

ATM Availability

ATMs are widely available and usually the most convenient way of obtaining Euros. Travellers cheques are accepted in banks. Credit cards are widely used.

Extra Expenses & Spending Money

Lunch is not included in the itinerary and some dinners are left open where there are good restaurant choices, please allow some spending money for this. We recommend approximately €5-15 (US$4.50-13) per lunch and €20-30 (US$18-27) for dinner.

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

Important Information

Your safe participation 

When booking this trip, you should be confident in your ability to participate in all activities described in these Trip Notes. If you have any doubt about your suitability, please call the Exodus office and ask to speak to one of the experts on this itinerary. 

Although our leaders are well trained to deal with different capabilities, if they have any concerns about someone’s ability to safely take part in an activity, or their impact on other people’s enjoyment, we authorise them to take necessary action which, in some circumstances, may involve asking someone to miss that activity. 

By booking this trip you agree to our Booking Conditions which clearly state that our leaders have the authority to do this. In these rare instances we will ensure anyone sitting out is safely provided for and offered alternative options where possible. Refunds will not be provided for activities missed and customers may be liable for additional costs incurred. 

How to Book

  1. Check availability: Go online to check availability, or contact us by phone or email.
  2. Secure your place: You can provisionally hold a place on this trip, usually for between three and seven days.
  3. Complete your booking and payment

When you’re ready to book, go to our website for online bookings, book over the phone or you can complete a booking form (available online or on request by calling us). We accept all major credit and debit cards, or you can pay be cheque.

After booking

You will receive your booking confirmation letter and invoice, which includes extra information and guidance about your travel arrangements.

Full joining instructions, including local emergency numbers and details of how to reach the start point, will be sent to you approximately two to three weeks prior to departure. If you do not receive these at least a week before departure, or require them earlier, please contact our office or your travel agent.

Trip Note validity

These Trip Notes are valid from the “Current as” date on page one. They will occasionally be updated after booking and before departure; if there are any updates that significantly impact the inclusions or itinerary, customers will be written to separately. They will also receive a link to the most up-to-date Trip Notes with their Final Joining Instructions before travelling.

The information in these Trip Notes is given in good faith. Where differences exist between the Trip Notes and our current brochure or website, the Trip Notes supersede the brochure and website. All holidays can be subject to unexpected changes; to enjoy them you should be prepared to be flexible where necessary. Occasionally, it may not be possible to follow the itinerary as planned. This may be for a variety of reasons – climatic, political, physical or other. In these circumstances we will make the best-possible alternative arrangements that maintain the integrity of the original itinerary.


Exodus is fully licensed and bonded as a tour operator. We hold Air Traffic Organisers Licence (ATOL) number 2582, issued and bonded with the Civil Aviation Authority (CAA). We are also bonded to the International Air Transport Association (IATA) and we are members of the Federation of Tour Operators (FTO) and ABTA – The Travel Association. This means you can book your Exodus holiday with confidence, as all money paid to us for your trip is fully protected.