San Gimignano & Volterra Short Break

San Gimignano & Volterra Short Break

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5 Days From

$658

San Gimignano & Volterra Short Break

5 Days Starting in San Gimignano, Italy and ending in Volterra, Italy

Visiting: San Gimignano, Certaldo, Volterra

Tour operator:

The Natural Adventure

Tour code:

507

Group Type:

Independent

Guide Type:

Self Guided

Physical rating:

Fit

Trip Styles:

Active

Activities:

Cycling, Sightseeing, Walking

From: $658

NB: Prices correct on 22-Dec-2024 but subject to change.

This tour is no longer available, please see similar tours below or send an enquiry

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

  • Arrive in San Gimignano and enjoy the breathtaking views of the Tuscan countryside.

  • Cycle through vineyards to the charming hilltop village of Certaldo, the hometown of Boccaccio.

  • Explore the ancient Etruscan town of Volterra, set on an imposing hill with stunning landscapes.

  • Experience the scenic ride through the Val d’Era and typical Tuscan white roads.

  • Discover the majestic beauty of the landscape sculpted by erosion near Volterra.

  • Enjoy panoramic views on the Strada del Cornocchio during a loop ride around Volterra.

Itinerary

Expand All

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

  • Accommodation in San Gimignano

    Accommodation is provided in San Gimignano for the duration of your stay there.

  • Accommodation in Volterra

    Accommodation is provided in Volterra during your stay in the ancient Etruscan town.

  • 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

  • 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.

  • Are airport transfers included in the tour package?

    Airport transfers are not included in the tour package unless booked as a supplementary extension.

  • 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.

  • 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.

  • 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.

  • 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.

  • 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.

  • 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.

  • 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.

  • 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.

  • 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.

  • 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

  • What policies are in place for Covid-19?

    We are part of the 'Safe Travels' initiative.

  • Can I join the tour once it has departed?

    Yes, as long as you can reach the next location.

  • 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)

  • 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.

  • 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.

  • 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

Reviews of this operator

Kicki Neely  

Walking Fishermens trail in western…

19-Sep-2022

Walking Fishermens trail in western Portugal will be a memory for life. We loved every minute of our week. All arrangements worked perfectly, from accommodation to luggage transport to questions we had before setting off. Our local agent met with us before we started the walk and we felt very reassured by his local knowledge and support. All accommodation was different, local, clean, friendly and easy to find. Very good value for money. I can really recommend Natural Adventure company and we will be back for more adventures. Many thanks Kicki Neely and friends

Marian Wilkins (Google Reviewer)  

A friend and I did...

25-Jan-2024

A friend and I did the Alps to the Riviera walk in France at the end of 2021 and it was the best holiday experience either of us has ever had. It’s an amazing way of immersing oneself in the countryside and getting the full flavour of the country away from the tourist attractions. The Natural Adventure Company made perfect arrangements for us, gave us clear directions and was just a call away, to sort out any issues. The walk gave us incredible memories that will enrich us for a lifetime. I am in the process of booking my next wonderful adventure and I can’t wait to get started!

Cathy O'Connor (Google Reviewer)  

I recently hiked, with a...

26-Jul-2024

I recently hiked, with a friend in the Italian Alps (the Val D'Aosta) and can highly recommend the region, and the Natural Adventure company. We were very pleased with the accommodation and the food was excellent most of the time- generous portions of excellent local dishes. The resources we were sent were excellent and very thorough. It was very easy to follow the routes as we were given so much detail- which we printed out and took each day's instructions with us, and the App helped to keep us on track. Sadly, we couldn't stay at the last location because there was a storm one night and the village we were due to stay in was flooded and cut off. The Natural Adventure did all they could to support us immediately, and help us find an alternative and we ended up staying where we were, as we were so pleased with that hotel and knew we could continue our hikes from there. We were very pleased with the holiday, the walks, the info and all our dealings with them. I would highly recommend them

Amanda Daly (Google Reviewer)  

We booked our self-guided Kumano...

15-Jul-2024

We booked our self-guided Kumano Kodo pilgrimage trip in Japan with The Natural Adventure (known locally as Oku Japan). The experience was top notch from beginning to end. The information packet was thorough and helpful, and details regarding trains and local buses (timetables, pricing, etc) were consistently accurate. Each and every accommodation was unique, charming, and welcoming. When there was an issue checking into our final hotel, the local office was quick to respond and the problem was solved within the hour (it was also a Sunday, so extra points). We weren’t expecting this to be a gourmet food tour of the region, but it was that as well! On top of it all, we found the price very reasonable for everything that is included. We had a wonderful experience thanks to The Natural Adventure, and would certainly travel with them again.

Cynthia Shinn (Google Reviewer)  

I have been working with...

26-Feb-2024

I have been working with The Natural Adventure for a few years now and it's been a flawless experience. I have now booked 4 different trips (4th to happen in April 2023). Accomodations have been great and local operators (bikes, hiking guides and boats) have all been great. The rates are very fair and trip selections are great. Hoping to see some boat bike options in Greece and Turkey!

Ellen Taylor-Powell  

Great communications, customized trip

20-Aug-2022

This is our first time using Natural Adventure to plan a hiking trip in Europe. I wanted an 8-day hike to start on a certain date to explore a northern region of Portugal. They were so accommodating - customized our trip to meet our needs with responsive communications and full itinerary; everything has been taken care of. We look forward to the trip!!

Linda Giovine (Google Reviewer)  

We hiked the Kerry Way...

02-Jun-2022

We hiked the Kerry Way with Natural Adventure and it was terrific. Outstanding views and good Irish weather. Some days were longer than expected due to placement of Bed and Breakfasts. Hosts were warm and helpful even dried our gear and shared local secrets. Irish hospitality in high gear.

Tim Fuhs (Google Reviewer)  

My wife and I booked...

14-Sep-2023

My wife and I booked the Lechweg short break hike with the natural adventure company this Fall and we’re very happy with our experience. I noticed one of the reviews questioning what they (natural adventure co) provide. That’s a fair question and from my perspective as a USA citizen, they provided a very important liaison/conduit role into the EU that would be prohibitive or downright impossible for a non EU citizen hiking/biking in Europe. In addition, I have found that in dealing directly with a few European companies directly, information does not always flow as smoothly as we like. The natural adventure company’s communication style fit our liking perfectly in that we receive a fast and thorough response with every question. They are prompt and helpful. They did subcontract with another company for boots on the ground support but the hotel reservations and itinerary were in house. We would definitely use the natural adventure company again no question.

Beverley Young  

Highly Recommended

03-Aug-2022

All the way through from booking, correspondence afterwards and now a wonderful holiday. The Natural Adventure have been helpful and have provided a brilliant holiday. The hikes each day are cracking, maps & routes are detailed and easy to follow. The hotels are great too. Completely love our holiday! Would definitely use The Natural Adventure again and recommend.

Jeanna Janssen (Google Reviewer)  

Really poor experience with my...

30-Jul-2024

Really poor experience with my recent Tour Du Mont Blanc trip. Our company contact Pierre was so unprofessional and did not care about the safety of travelers. On the second day he left to do a hike and we didn’t hear back until multiple days later. I experienced multiple travel delays which meant the loss of the prepaid travel arrangements and their solution was a 250 euro taxi to the hotel. Do not recommend.

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$676

Monday - Friday

Oct 06, 2025 - Oct 10, 2025
$676

Tuesday - Saturday

Oct 07, 2025 - Oct 11, 2025
$676

Wednesday - Sunday

Oct 08, 2025 - Oct 12, 2025
$676

Thursday - Monday

Oct 09, 2025 - Oct 13, 2025
$676

Friday - Tuesday

Oct 10, 2025 - Oct 14, 2025
$676

Saturday - Wednesday

Oct 11, 2025 - Oct 15, 2025
$676

Sunday - Thursday

Oct 12, 2025 - Oct 16, 2025
$676

Monday - Friday

Oct 13, 2025 - Oct 17, 2025
$676

Tuesday - Saturday

Oct 14, 2025 - Oct 18, 2025
$676

Wednesday - Sunday

Oct 15, 2025 - Oct 19, 2025
$676

Thursday - Monday

Oct 16, 2025 - Oct 20, 2025
$676

Friday - Tuesday

Oct 17, 2025 - Oct 21, 2025
$676

Saturday - Wednesday

Oct 18, 2025 - Oct 22, 2025
$676

Sunday - Thursday

Oct 19, 2025 - Oct 23, 2025
$658

Monday - Friday

Oct 20, 2025 - Oct 24, 2025
$658

Tuesday - Saturday

Oct 21, 2025 - Oct 25, 2025
$658

Wednesday - Sunday

Oct 22, 2025 - Oct 26, 2025
$658

Thursday - Monday

Oct 23, 2025 - Oct 27, 2025
$658

Friday - Tuesday

Oct 24, 2025 - Oct 28, 2025
$658

Saturday - Wednesday

Oct 25, 2025 - Oct 29, 2025
$658

Sunday - Thursday

Oct 26, 2025 - Oct 30, 2025
$658

Monday - Friday

Oct 27, 2025 - Oct 31, 2025
$658

Tuesday - Saturday

Oct 28, 2025 - Nov 01, 2025
$658

Wednesday - Sunday

Oct 29, 2025 - Nov 02, 2025
$658

Thursday - Monday

Oct 30, 2025 - Nov 03, 2025
$658

Friday - Tuesday

Oct 31, 2025 - Nov 04, 2025
$658

Book with Confidence

  • 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.

  • 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.

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