Tuscany & Siena – Independent
Cross central Tuscany on foot, following the same pilgrim paths that were once congested with many thousands of people on their way to Rome or Canterbury and all the trading towns in between. Today these ancient tracks are quiet but the impression of this bygone era remains. Travel through a landscape of rolling hills crowned by hilltop villages. Lines of cypress trees highlight the contours while vineyards and olive groves blanket the slopes.
The route is punctuated by intact medieval towns, culminating in the glorious art and architecture of Siena. The charm of this region is its changelessness, merging medieval and modern worlds.
Duration: 5 or 8 days
Itinerary
This ramparted medieval and Renaissance town affords commanding views over the route that lies ahead. Famous for its association with Boccaccio, author of 'The Decameron'.
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.
Charming ‘castle’ in very central location, with garden and wonderful views
Follow a ridge offering superb views of the surrounding countryside, before paths descend into a valley. Follow vineyards onwards and up towards iconic San Gimignano, Italy's 'medieval Manhattan' (10.2 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.
Comfortable hotel in medieval centre
Upgrade rooms are larger
Opportunities to explore the walled medieval town. Optional circular walk in the countryside around San Gimignano, offering superb views of the town (5.5 miles, 2.5 hours).
In addition to the cultural delights of San Gimignano, this is the place to do your shopping – local wines, wild boar products, olivewood, pottery and leather goods at reasonable prices!
Comfortable hotel in medieval centre
Upgrade rooms are larger
Walk across low hills with vines, woods, olive groves, and views of an almost unchanged medieval landscape... to the ancient walled town of Colle di Val d’Elsa, renowned for its perfectly preserved medieval ‘tunnel’ streets (also noted for its crystal glass and ice creams!) (8.7 miles, 4.5 hours).
Less crowded than the likes of San Gimignano and Siena, ‘Colle’ holds true to itself as a working town with an innovative people. The wool, paper and flour industries previously thrived here while today it is crystal and fine glass. Explore the old town on the volcanic ridge before visiting the glass museum in the lower town.
Elegant hotel in medieval village with spa and restaurant
Upgrade rooms are larger
Follow farm tracks and gravel lanes across fertile farmland, with olive groves and vineyards, to the Romanesque abbey of Abbadia Isola. Continue on to Monteriggioni, a tiny medieval village with just 85 inhabitants, encircled by 13th century walls with 14 watchtowers (11.9 miles, 6 hours).
A beautifully sited and perfectly preserved village encased within 13th century walls, complete with watchtowers. In the main square is a small Romanesque church with a pretty façade. An idyllic spot to wander.
Friendly accommodation on main square
(room only)
Walk through forests, past a castle, across open farmland and wooded slopes. Wonderful views on the approach to Siena, the best-preserved great medieval city in Europe (11.9 miles, 6 hours or 11.6 miles, 6 hours to upgrade hotel).
Radiating from the magnificent Piazza del Campo, home to the world-famous, spectacular bareback horse race Il Palio, Siena has an impressive cityscape combining Gothic and Romanesque styles, and many excellent shops, bars and restaurants!
Modern hotel within the city walls
Luxurious, centrally located, well-appointed hotel
Opportunities for exploring the medieval city and optional Siena city walk (3.5 hours).
Explore Siena with its abundance of outstanding 14th and 15th century art and architecture. Visit the stunning Duomo (cathedral) incorporating the Libreria Piccolomini. Opposite lies Santa Maria della Scala - an ex-medieval hospital with frescoes and half a dozen small museums that stretch through tunnels inside it.
Modern hotel within the city walls
Luxurious, centrally located, well-appointed hotel
Trip Planner
Walking & Terrain
Walking: Easy to moderate. Hill climbs are generally gentle, with the exception of a steeper ascent up to Monteriggioni. There are longer days of walking to Monteriggioni and Siena. The walk lengths vary from 2.5 hours to a maximum of 6 hours walking. Hours of walking, which may vary from individual to individual, means hours of actual walking and does not include stops for lunch, sightseeing or rests.
Terrain: The route is through rolling countryside following gravel roads (strade bianche), farm tracks and woodland paths, with some tarmac on the approach to towns. On certain days the walk takes you into the hills where the paths cross a more rugged terrain – please make sure that your footwear provides sufficient ankle support. There are no vertiginous sections.
All ATG trips include facilities and options so that you can arrange to walk as much or as little as you like – or not at all - and your Route Manager will be able to advise you on public transport or taxi options.
Walking & Terrain
Walking: Easy to moderate. Hill climbs are generally gentle, with the exception of a steeper ascent up to Monteriggioni. There are longer days of walking to Monteriggioni and Siena. The walk lengths vary from 2.5 hours to a maximum of 6 hours walking. Hours of walking, which may vary from individual to individual, means hours of actual walking and does not include stops for lunch, sightseeing or rests.
Terrain: The route is through rolling countryside following gravel roads (strade bianche), farm tracks and woodland paths, with some tarmac on the approach to towns. On certain days the walk takes you into the hills where the paths cross a more rugged terrain – please make sure that your footwear provides sufficient ankle support. There are no vertiginous sections.
All ATG trips include facilities and options so that you can arrange to walk as much or as little as you like – or not at all - and your Route Manager will be able to advise you on public transport or taxi options.
Additional activities available locally
This is a wonderful area offering additional local experiences for the free day in San Gimignano. The circular walk on this day can include a local wine tasting with lunch or Truffle hunting.
Wine tasting - 40€/person
Lunch and wine tasting - 55€/person
Truffle hunting and wine tasting (weekends in the Autumn only) - 110€/person
Additional activities are paid for locally and can be booked via your Route Manager who will contact you 2 weeks prior to departure.
Your Personal ATG Route Manager
I grew up in Poland and have had the wonderful opportunity to study and work in Italy. Since 2018, I’ve been part of ATG and, right now, I’m enjoying life in beautiful Tuscany! What I love most about my job is the chance to explore so many amazing parts of Italy including hidden gems that aren’t typically on tourists’ radar. It really feels special to experience the authentic charm of Tuscany with its rolling hills, vineyards and picturesque countryside and I look forward to welcoming you.
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
You can expect each hotel to be one of the most characteristic, comfortable and best located for travellers on foot, with the character and sometimes the standard varying from place to place.
Star ratings indicate official classification, although many delightful places have no star rating. In more remote areas hotels may be of a generally lower standard in relation to their ‘star ratings’.
Single travellers are accommodated in double rooms for single occupancy for a supplemental charge.
On this route, upgraded accommodation is available at some overnight stops, as specified on the itinerary.
Breakfast is included and there are suggestions in the Route Book about where to buy provisions for a picnic lunch, as well as restaurant recommendations. Dining options often include a choice of restaurants that can be pre-booked for you by your Route Manager.
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. Many of the villages have a selection of enoteca, or wine shops, for tasting and buying wines. You will also pass wine estates where sampling and direct sales are possible. 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. The incredible riches that accumulated laid the foundations for the Renaissance, the seismic cultural movement that began in Florence and then spread throughout Europe. Our Route Book provides further detailed pages on the history of Tuscany.
Flora & Fauna
There are delightful woodland and wayside flowers in spring as well as plenty of birdlife. In May and June you can enjoy poppy fields and fireflies. In late June to July there are bright 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.
Travel arrangements
Travel arrangements, including flights, for ATG Independent Footloose trips should be made independently.
Outward travel to Certaldo:
From Pisa airport, take the ‘People Mover’ shuttle train to Pisa Central station, and a train from there to Certaldo, changing trains at Empoli.
From Florence airport, take the tram line to the central station in Florence (Firenze Santa Maria Novella), then a train via Empoli to Certaldo.
Outward travel to San Gimignano:
From either Pisa or Florence, there are trains via Empoli to either Poggibonsi or Certaldo and continue by bus (from Poggibonsi) or taxi (from Certaldo) to San Gimignano.
Return travel from Siena:
There are frequent trains from Siena back to either Florence or Pisa central stations, then connect to the tram line for Florence airport, or the shuttle train to Pisa airport.
Trip Options & Prices
Overview
This 5 day independent walking tour in Tuscany starts in iconic San Gimignano and includes 3 days of walking for those looking for a dedicated walking trip. Enjoy a short break with scenic walking, archetypal Tuscan landscapes, medieval hilltop towns and the great Art city of Siena.
Itinerary
Day 1: Arrive in San Gimignano*
Day 2: San Gimignano to Colle di Val d’Elsa*
Day 3: Colle di Val d’Elsa to Monteriggioni
Day 4: Monteriggioni to Siena*
Day 5: Departure
*The upgrade price option includes upgrades at these locations
Prices (per person)
Overview
This 8 day independent walking tour in Tuscany is a more in-depth visit of the area. Starting in medieval Certaldo, this trip includes 4 days walking and ‘free days’ in San Gimignano (with optional walk) and Siena to discover more of the delights of these two medieval icons of Tuscany.
Itinerary
Day 1: Arrive in Certaldo
Day 2: Certaldo to San Gimignano*
Day 3: San Gimignano* - free day
Day 4: San Gimignano to Colle di Val d’Elsa*
Day 5: Colle di Val d’Elsa to Monteriggioni
Day 6: Monteriggioni to Siena*
Day 7: Siena* - free day
Day 8: Departure
*The upgrade price option includes upgrades at these locations
Prices (per person)
Our Independent Footloose itineraries have the flexibility to be customised if you would like to spend more time in any of the places en route; perhaps to incorporate some of the add-ons available locally or just to create a more relaxed pace to your holiday.
If you wish to build your own itinerary please complete our customise form and our Sales team will provide you with a bespoke quote.
Frequently Asked Questions
On each route there is an ATG Route Manager, who is there to take care of all the practicalities and ensure the success of your trip. Route Managers have all been ATG-trained, speak English and the language of the country fluently, and live in the local area. Your Route Manager will make contact with you a couple of weeks prior to departure (usually by email) and will then meet you at the start of your trip and will be available during your trip to move your luggage from hotel to hotel, provide local information, make restaurant reservations and do everything possible to ensure that you derive maximum enjoyment from your holiday.
Please let us know about any dietary restrictions or allergies in advance so that our Route Manager can ensure that you are catered for during your holiday. Most dietary restrictions do not present a problem on our trips and the Route 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.
If you are planning to take an Independent trip as a single traveller, we would ask you to consider the potential dangers of walking alone before making a booking and if necessary discuss this with our Sales team.
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.
The trips in our Independent programme make ideal family holidays for those with children who are old enough (and keen enough!) to enjoy a walking holiday or young enough to be carried in a backpack.
You would need to consider costs for lunches (either a picnic style lunch or lunch in a café as you prefer) and evening meals. Where an evening meal is included at a hotel this is indicated on the trip page. For evening meals not included, the route book provides restaurant recommendations to suit a wide range of budgets. You would also need to factor in any entrance fees to museums, churches, galleries and other sightseeing costs, items of a personal nature, shopping expenditure and transport if you choose to not to walk on some days.
Tourist Tax
This tax is charged per guest per night and the rate is determined by the local council based on the star rating of the accommodation. The rate usually varies from €2 up to €5 per person per night, although the rate can be higher in major cities. This tax is not included in the price of your holiday but where applicable will be payable direct to your hotel in cash.
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 Route Manager will be able to tell you about the ATG Trust project on this route involving the restoration of the Porta Romea in Monteriggioni. This restoration formed part of a much larger project to restore the walls around the medieval village of Monteriggioni. The Porta Romea is the gateway facing Rome through which many ATG clients will have walked.
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