San Gimignano & Volterra Short Break
San Gimignano & Volterra Short Break
San Gimignano & Volterra Short Break
5 Days Starting in San Gimignano, Italy and ending in Volterra, Italy
Visiting: San Gimignano, Certaldo, Volterra
Tour operator:
Tour code:
507
Group Type:
Independent
Guide Type:
Self Guided
Trip Styles:
Interests:
Activities:
Tour Overview
Embark on a captivating cycling adventure through the heart of Tuscany with the San Gimignano & Volterra Short Break. Begin your journey in the picturesque town of San Gimignano, where you'll be enchanted by the rolling hills and lush vineyards. Pedal your way to the historic village of Certaldo, the birthplace of Boccaccio, and explore its charming streets. Continue your ride to the ancient Etruscan town of Volterra, perched atop a hill with breathtaking views. Experience the thrill of cycling through the scenic Val d’Era and along the iconic Tuscan white roads. Choose from various cycling routes, ranging from 35 to 60 km per day, and enjoy stays in delightful accommodations, including a former convent in Volterra's old city center. This tour offers a perfect blend of culture, history, and stunning landscapes, making it an unforgettable Tuscan escape.
Highlights
Itinerary
Day 1 : Arrive In San Gimignano
Location: San Gimignano
Accommodation Name: Accommodation: in San Gimignano
Arrive at your hotel in San Gimignano and unwind, as this will be your base for the next few days. Breathe in the wonderful country air and take a stroll along the classic green rolling paths, marvelling at the breath-taking views of the surrounding countryside. Immerse yourself in the Tuscan tranquillity.
Day 2 : Vineyards Of Ulignano, Certaldo Alto & Barberino
Location: Certaldo
Accommodation Name: Accommodation: in San Gimignano
Today you will cycle through many vineyards towards Ulignano and the charming hilltop village of Certaldo, the hometown of the renowned Italian writer Boccaccio. You can get to Certaldo, either by a funicular train or by cycling on a steep section. After visiting its ceramic-decorated main square and stunning churches, you can choose an extended ride to Barberino and Tavernelle in the Chianti Classico area, offering magnificent views.
Day 3 : San Gimignano To Volterra
Location: Volterra
Accommodation Name: Accommodation: in Volterra
Today, you will leave San Gimignano behind and cycle to the ancient Etruscan town of Volterra. Through a patchwork-like landscape dotted with wheat fields, olive groves and villas, you reach the base of the imposing hill on which the town is located. It takes one more solid climb before you arrive at your marvellous hotel, a former convent set inside in the gates of the old city centre.
Day 4 : Volterra Loop Rides
Location: Volterra
Accommodation Name: Accommodation: in Volterra
Today you can choose between two options:
Option 1: Volterra to Montecatini Val di Cecina
After an exhilarating downhill ride into the valley, you cycle through the lovely Val d’Era and over stretches of ‘strade bianche’, typical Tuscan white roads. The itinerary winds through the landscape filled with remote farmsteads and villas, and hills covered with vines and olive groves. Grand views on the vast undulating terrain will accompany you throughout the entire day.
Option 2: Loop ride via Ulignano
An easy and very scenic ride in the surroundings of Volterra. Erosion caused by rainwater has artistically sculpted the landscape, creating cracks and gullies of majestic beauty. After descending from Volterra, you will venture off the beaten track on unpaved tracks, returning on the very panoramic Strada del Cornocchio.
Day 5 : Departure
Meals Included: Breakfast
The trip and our services end after breakfast unless you have booked a transfer to the airport or other supplementary extensions.
What's Included
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Accommodation in San Gimignano
Accommodation is provided in San Gimignano for the duration of your stay there.
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Accommodation in Volterra
Accommodation is provided in Volterra during your stay in the ancient Etruscan town.
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Cycling Routes
Cycling routes are included, offering options for different distances and scenic views.
What's Not Included
Airport transfer is not included unless booked as a supplementary extension.
Mode of Transport
Enjoy scenic cycling routes through Tuscany, with options ranging from 35 to 60 km per day, exploring vineyards, hilltop villages, and ancient towns.
Accommodation
Stay in charming accommodations in San Gimignano and Volterra, including a marvellous hotel set in a former convent within the gates of Volterra's old city centre.
Check out our Q&As
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What type of accommodation can I expect during the tour?
You will stay in charming accommodations in San Gimignano and Volterra, including a marvellous hotel set in a former convent within the gates of Volterra's old city centre.
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Are airport transfers included in the tour package?
Airport transfers are not included in the tour package unless booked as a supplementary extension.
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What are the cycling route options available during the tour?
The tour offers scenic cycling routes through Tuscany, with options ranging from 35 to 60 km per day, exploring vineyards, hilltop villages, and ancient towns.
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What can I expect on the first day of the tour?
On the first day, you will arrive at your hotel in San Gimignano, unwind, and take a stroll along the classic green rolling paths, enjoying the breathtaking views of the surrounding countryside.
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What activities are planned for the second day of the tour?
On the second day, you will cycle through vineyards towards Ulignano and Certaldo, the hometown of Boccaccio. You can visit its ceramic-decorated main square and stunning churches, with an option to extend the ride to Barberino and Tavernelle in the Chianti Classico area.
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What is the highlight of the third day of the tour?
The highlight of the third day is cycling from San Gimignano to the ancient Etruscan town of Volterra, through a landscape of wheat fields, olive groves, and villas, culminating in a climb to your hotel, a former convent in the old city centre.
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What are the cycling options on the fourth day?
On the fourth day, you can choose between two cycling options: a ride to Montecatini Val di Cecina through the Val d’Era and typical Tuscan white roads, or a loop ride via Ulignano, featuring scenic views and unpaved tracks.
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What happens on the last day of the tour?
On the last day, the trip and services end after breakfast unless you have booked a transfer to the airport or other supplementary extensions.
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What Ethical Travel credentials does the tour company have?
The Natural Adventure was founded by people who love hiking and cycling in wild and wonderful places. Places that we want to keep that way. Responsible tourism has, therefore, been at the heart of what we do since the get go.
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Am I contributing to any charity by booking the tour?
In April 2020 as a response to the COVID-19 crisis, we launched the Support Local Communities Initiative. We have enabled an option when booking a tour for customers to make a donation to support our local partners. 100% of the donations go directly to our local suppliers.
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Who will be my travelling companions on the tour?
Whether you’re travelling on your own, as a couple, a group of friends, or a family, our self-guided holidays allow you the freedom to choose your own holiday companions.
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What documents will I receive before I travel?
Our self guided walking and cycling holidays typically include: Accommodation, Breakfasts, Luggage transfers, Detailed holiday information pack including GPS-checked and regularly updated route descriptions, road notes and maps, 24/7 phone assistance by our local representative and/or our central office
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What policies are in place for Covid-19?
We are part of the 'Safe Travels' initiative.
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Can I join the tour once it has departed?
Yes, as long as you can reach the next location.
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Do you operate a “single share” option and how does it work?
Accommodations in double or twin rooms (solo travellers are usually accommodated in single rooms at an extra cost; we never mix and match)
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What happens if I need to change my holiday date once I’ve booked?
If possible, and entirely at the discretion of the Tour Operator, a change of the dates may be possible without charging an amendment fee, provided that it is requested at least 30 days before the departure date. In some cases, we will still have to pass to you any non-refundable charges imposed by our suppliers. In all other cases, change of dates will normally be treated as a cancellation.
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Will the accommodation included meet local health and safety regulations?
All places have been carefully checked by us and their quality is regularly monitored. We have selected accommodations that offer friendly service, clean and comfortable rooms and local flavour.
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How long has the tour company been trading?
The Natural Adventure was founded in the UK in 2009, by Peter Duncan, former UK Chief Scout and BBC Blue Peter presenter, and Alex Pazderski, an avid hiker and acclaimed expedition kayaker. Both natural adventurers and keen explorers of wild places and trails, remote communities and responsible tourism partners, Peter and Alex founded our company inspired by the responsible travel values t
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Oct 31, 2025 - Nov 04, 2025Book with Confidence
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Low Deposit
The Natural Adventure requires a minimum deposit of 20% or the full booking value, whichever is less, with the final balance not due until 42 days before departure.
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Cancellation Policy
We don't charge a cancellation fee, here is a summary of the natural adventure charges.
Up to 42 days before tour starts: Forfeit 100% of deposit.
At 30 days before tour starts: Forfeit 50% of booking price.
At 14 days before tour starts: Forfeit 100% of booking price.