Florence to San Gimignano & Volterra – Escorted
Walk back millennia in time, following ancient routes of the Via Volterrana from renaissance Florence, through the picturesque landscapes of archetypal Tuscany spending nights in iconic medieval walled hill towns before arriving in one of the great cities of the ancient world - Volterra.
This route is punctuated by characteristic cypress trees, olive groves, forested hills, fine views and some notable Chianti vineyards, with a night on a wine estate, and others in iconic hill towns - lively San Casciano Val di Pesa with its high defensive wall and fine Art museum, Certaldo with its towering brick ramparts, San Gimignano, the 'medieval Manhattan’ with its famous towers, once an overnight stop on the main Via Francigena road to Rome, and Volterra with its 3 miles of 2,500 year-old walls, excellent Etruscan museum, Roman theatre and fine medieval town… All this and comfortable hotels, interesting restaurants and excellent local wines.
Duration: 8 days
Trip dates:
25 Oct - 01 Nov 2026
Itinerary
Arrive in Florence: World-Class sightseeing (& shopping!). NOTE!! An extra (free) night in Florence pre-tour is included in the tour price. In this instance a transfer at the start of the tour is not included.
This magnificent city built on the banks of the Arno was the cradle of Renaissance of the arts in Italy under the aegis of the powerful ruling Medici family. Now, the world’s foremost ‘Art City’ with museums and art galleries galore, most notably the Uffizi. The Duomo (cathedral) and numerous churches across the city also house outstanding art and architecture. Together with its elegant shops and restaurants this is one of the most fascinating cities to visit in Europe.
Elegant hotel located in the historic centre
From the Ponte Vecchio, follow roads and ancient lanes to La Certosa, the Cistercian monastery at Galluzzo, from where quiet lanes lead up through vineyards and olive groves to our comfortable countryside hotel (12.7 miles, 7 hours).
Inhabited since Etruscan times and situated on a bluff high above the River Pesa, the town was a strategic military outpost protecting medieval Florence from invasion by the Sienese to the south. Today, the town is known for its top-quality wine and olive oil. One of Italy’s most famous wine producers, the Florentine noble family of Antinori, have their main cellars just outside the town.
Historical house with garden and pool
We walk to medieval San Casciano, with churches and museums containing 14C works by Ambrogio Lorenzetti. Paths lead down into the fertile Pesa Valley, then up through olive groves and vineyards (8.3 miles, 4 hrs). From the wine estate where you stay there is a 10 minute walk to the 9th century Pieve di San Pancrazio.
Renowned for the 10th-century Pieve di San Pancrazio. Works of art inside the church include a 14th-century Madonna and Child by Cenni di Francesco and a Crucifixion by Santi di Tito of 1590, as well as portraits of Dante, Boccaccio, Petrarch, Sophocles, Socrates and Virgil.
Farm and wine estate in lovely setting, with pool
Paths with some inspiring panoramic views lead across picturesque hills and valleys to the Elsa Valley and the small, walled medieval hill town of Certaldo, with its fine brick ramparts, and house of Giovanni Boccaccio, where in 1349 he wrote The Decameron (11.6 miles, 6 hours). Brief transfer to our hotel in San Gimignano.
A classic Tuscan hilltop town with Etruscan roots and once a prominent stop on the Via Francigena pilgrim route. It is divided into the quieter medieval upper town, steeped in history, culture and art, and the more modern lower town, bustling with everyday life. Certaldo is perhaps best known for its associations with the Italian poet and writer Giovanni Boccaccio, who lived and died here. Visit his former house and his tombstone in the church of Santi Jacopo e Filippo.
Comfortable hotel in the medieval centre
After a brief transfer back to Certaldo: Strade bianche-lined with cypress trees and paths through vineyards, olive groves and woods lead to San Gimignano, ‘the medieval Manhattan’ (10.1 miles, 5 hours).
The ‘city of the towers’ is irresistibly charming and perfectly preserved. Highlights include the Collegiata (former cathedral) with wonderful frescoes, the Museum of Modern Art, Museo Civico (Civic Museum, which includes a chance to climb the Torre Grossa, the city’s tallest tower) and Museum of Torture. This is the place to do your shopping – local wines, wild boar products, olivewood, pottery and leather goods.
Comfortable hotel in the medieval centre
Paths lead down across a valley and then through forest before climbing to a ridge with views to Volterra. After following a strada bianca down into the Era Valley, an ancient path leads up (and up!) to the great Etruscan city of Volterra (16 miles, 9 hours).
Volterra is less visited than other Tuscan hilltop towns yet has so much to offer. One of the largest and most important of the 12 Etruscan city states, it still features the remains of Etruscan walls, two Etruscan-Roman gateways, and circular tombs from the 6th century BC, as well as a well-preserved Roman theatre and baths.
Friendly, centrally located hotel. Outdoor terrace with panoramic views
Free day to explore Volterra's three miles of Etruscan Walls, Etruscan tombs and excellent Etruscan mseum, cathedral and medieval town. Optional circular walk (3 miles, 2 hours).
It's worth visiting one of the workshops within the town where you can see alabastrai, at work. These artisans sculpt alabaster – an age-old tradition in Volterra. This soft, white rock has a beautiful translucent quality, perfect for carving into decorative objects (and taking home as a souvenir).
Friendly, centrally located hotel. Outdoor terrace with panoramic views
Transfer to Pisa and Florence airports.
Trip Planner
Walking & Terrain
Moderate walking. The walking is mostly gentle hills with the occasional short, steep ascent thrown in. Day 6 is the most demanding – a long but very rewarding walk, ending with a steep ascent to Volterra. There are no vertiginous sections.
Terrain includes well-made farm and woodland tracks, stony dirt roads (strade bianche) and small country lanes. There are one or two ‘cross country’ sections that may be muddy after rain (April/October in particular) and some narrow woodland paths.
Our support vehicles allow you the flexibility to walk 'as much or as little as you like', with drop-offs and pick-ups appropriate to the given day's itinerary. The Tour Leader will tell you each evening about the following day's walking options.
Walking & Terrain
Moderate walking. The walking is mostly gentle hills with the occasional short, steep ascent thrown in. Day 6 is the most demanding – a long but very rewarding walk, ending with a steep ascent to Volterra. There are no vertiginous sections.
Terrain includes well-made farm and woodland tracks, stony dirt roads (strade bianche) and small country lanes. There are one or two ‘cross country’ sections that may be muddy after rain (April/October in particular) and some narrow woodland paths.
Our support vehicles allow you the flexibility to walk 'as much or as little as you like', with drop-offs and pick-ups appropriate to the given day's itinerary. The Tour Leader will tell you each evening about the following day's walking options.
Your Personal ATG Route Manager
Route Book
The ATG Route Book is a detailed, day-to-day guide. The book anticipates your needs with easy-to-follow instructions, maps, plans and other information that will guide you to discover the best that the area has to offer and is the key to the success of an independent holiday with us.
Walking App
Your Route Manager can provide you with a link to download an app to your smartphone. This app provides the GPS track for your route on your phone. You can use this digital support to find your position and navigate the route, even without an internet connection or mobile phone reception.
Accommodation & Meals
The hotels we stay in are characteristic of the area and the towns we visit.
All evening meals are included and are taken either in the hotel or in local restaurants. At dinner, the Tour Manager will tell you about each evening’s menu and if there is anything else that you would prefer, you only have to ask. There are no particular dress requirements in the restaurants we use, although some are obviously smarter than others.
Each day the Tour Manager will meet you with one of ATG’s celebrated picnic lunches. You will be greeted with mineral water and a starter followed by wine and an abundant lunch of local organic produce and specialities. Picnics are colourful, varied and nutritious. Buffet-style, there is a choice of meats, cheeses, substantial salads, bread and fruit…and pudding. If it is cold there will be a hot dish.
Food & Wine
Tuscan food is simple and earthy. Menus feature rich bean soups, bread served alongside salamis and tangy sheep cheeses, slow-cooked wild boar or rabbit stews and spiced cakes full of candied fruits and nuts. This all complements the robust wines of the region. You will be walking through the vineyards of Italy’s most famous wine, Chianti. You may also like to try a further selection of local wines including Vernaccia, a white wine of Tuscany for which nearby San Gimignano is famous, and the delicious local ‘passito’ dessert wine, Vin Santo. The Route Book contains a section on the cuisine and wines of the region, and a list of recommended restaurants en route. The Route Manager will be pleased to help you with any queries, requests or advice.
History
The history of Tuscany has been one of invasion and conquest from earliest times. Yet interspersed within these periods of war and rivalry were times of great cultural, political and economic brilliance. These were most notably during the Etruscan period from the 8th century BC, and then from the 12th century when many Tuscan cities prospered finding great wealth through new-found trades. You will be walking the Via Volterrana, an ancient trade route along which salt was transported from Volterra, where it was mined, to Florence, where merchants sold this ‘white gold’. Our Route Book provides further detailed pages on the history of Tuscany.
Flora & Fauna
There are woodland and wayside flowers in spring and autumn and plenty of birdlife, particularly in the Spring. In May and June you can enjoy poppy fields and fireflies! In late June to July there are good displays of sunflowers and butterflies. Autumn sees cyclamen flowering again in the woods and the vendemmia or grape harvest. Our Route Book provides further detail while apps such as ‘LeafSnap’, ‘Flora Incognita’, ‘ChirpOMatic’ and child-friendly ‘Seek by iNaturalist’ can identify the flora and fauna en route.
Frequently Asked Questions
Escorted trips are accompanied by two of ATG’s fully trained Tour Consultants, from the moment they welcome you at the airport, through to the end-of trip airport transfer. The Tour Manager looks after the practical side of the trip – luggage transport, hotels, food and drink. The Tour Leader will lead each day’s walk, and after dinner each evening will tell you about the following day’s itinerary. Both Tour Consultants will explain their role, and how the trip will run, on the first evening at dinner.
Please let us know about any dietary restrictions or allergies in advance so that our Tour Consultants can ensure that you are catered for during your holiday. Most dietary restrictions do not present a problem on our trips and the Tour Manager can discuss your requirements in more detail with you at the start of your trip.
The walks are graded according to difficulty but you can walk as much or as little as you like.
Easy: walking along well-established paths and tracks with some short ascents/descents. These trips are suitable for most people who enjoy occasional exercise.
Easy to Moderate: walking along well-established paths and tracks. Occasional loose (gravel) surfaces. Ascents/descents up to 1 hour. These trips are suitable for most people who have a reasonable level of fitness.
Moderate: walking along a variety of paths and tracks. Occasional uneven areas. Ascents/descents 1-2 hours. These trips are suitable for those who have a reasonable to good level of fitness.
Moderate to Challenging: walking along varied paths and surfaces, occasionally challenging, with ascents/descents of 2-3 hours. These trips are suitable for more experienced walkers who have a good level of fitness.
Single travellers will be booked into a double room which will carry a single occupancy supplement.
Flights are not included in the price of your ATG holiday and should be booked independently. We will advise you of the group meeting time at the destination airport and return transfer time to the airport at the end of your trip to enable you to book compatible flights.
Yes. All of our escorted trips can be booked privately, you can book a set departure or a date to suit you (subject to availability). In most instances if the group is 13-16 clients we will offer the trip at the published price. For 12 or fewer clients we would provide a bespoke costing.
On escorted trips everything is included (per the published itinerary) apart from items of a personal nature and snacks or drinks outside of the set meals.
We are delighted to book extensions for you at either end of your trip. We only book hotels with which we have an established relationship and where we can ensure a high level of service and enjoyment. If you would like an extension hotel booking please indicate this during the booking process and we will contact you with pricing information.
ATG does not provide any form of insurance cover. However, it is a condition of booking that you have fully comprehensive insurance cover, including:
Cancellation/curtailment up to the cost of the holiday (preferably including flights)
Medical emergencies and repatriation
Travel delay / missed departure
Lost or stolen personal belongings
Personal liability
Legal expenses
Natural Disasters
Although most credit card companies offer travel insurance as something that is included when paying the balance with the card, it may be advisable to check that the cover offered is what you expect it to be. Very few companies include cancellation and curtailment or medical expenses. Whatever the insurance policy you have taken out, please read the documentation carefully. Please ensure also that you take it with you on your trip and refer to it in the case of any claim or emergency.
Yes, please click here for what to bring. A packing checklist is also included with your booking confirmation.
Sustainability
ATG was founded on principles of conservation and sustainable development. It was the first company to win the tourism industry’s two top awards: Tourism for Tomorrow (UK) and the World Legacy Award (National Geographic and Conservation International USA) and also the first to have an accredited Environmental Management System.
Everyone who walks with ATG contributes to the ATG Trust, which funds projects that benefit local communities in the regions visited. By supporting these initiatives, ATG promotes sustainable tourism. Past projects have included heritage restoration projects, environmental conservation and educational projects.
Your Tour Leader will be able to tell you about the ATG Trust project on this route involving the restoration of part of the Via del Sale (Salt route) between San Gimignano & Volterra, including the clearing of paths and vegetation, installation of wooden seating and tables, plus information panels detailing the historical, cultural and environmental information about the route.
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