7 days

Tuscan Trails (self-guided)

Tuscan Trails (self-guided)

UNESCO World Heritage-listed medieval Siena

Tuscan towns and villages

Ancient Via Francigena

Trip rating
  • If you’re looking for the perfect Tuscan itinerary where you can go at your own pace then this self-guided trip might be just right! Over seven days you’ll get under the Tuscan sun during the day and by night you’ll sleep in convents and beautiful agriturismos (farmstays).

    Why we love it

    • Through an extensive footpath network, follow in the footsteps of medieval pilgrims on the Via Francigena - one of Europe’s most important ‘highways’ in ancient times
    • Sample the local drop at Colle di Val d’Elsa, a rural treasure perched on a ridge overlooking rolling fields, and explore the rich scatter of museums, galleries and piazzas
    • Wander rolling hills, world-famous vineyards, olive groves and fields of sunflowers through to charming farmhouses
    • A feature of this tour is a stay in one of Tuscany’s most beautiful 'agriturismos' and a night in the famed convent at Monte Oliveto Maggiore


    Day 1 - Arrive Colle Val d'Elsa

    • Your trip starts with your arrival in Colle Val d‟Elsa, situated in the heart of Tuscany. The town is accessible by private taxi or public bus from Florence (52km) or Siena (27km). The closest airports are Florence (1 hour) or Pisa (2 hours).
    • After settling into your hotel, which is located in the old town, you may wish to take walk around the town centre, known for its perfectly preserved tunnel like streets and its crystal ware.

    Day 2 - Colle Val D'Elsa - San Gimignano

    • Your walk today takes you at first through the whole historical town centre of Colle Val D’Elsa, perhaps not as famous as its neighbouring Tuscan towns, but with a very interesting old town centre.
    • You will then descend into the valley where you will pick up one of the routes of the ancient Via Francigena. Along this route, through a pleasant, hilly landscape of vineyards and forests you will reach the small hamlet of Bibbiano.
    • Another descent will bring you to the valley of the Foci River with a short stretch through the river valley and past an old water mill.
    • You will then start to climb along a comfortable track up to a beautiful 'agriturismo' (farm estate), where you will spend the next two nights.
    • It's recommended you start early today to make sure you have plenty of time at the property to enjoy its fabulous setting and surroundings, and perhaps its library or swimming pool.
    • For those who wish, there is also a longer option to walk to this point.
    • Tonight dinner will be included at the private restaurant of the agriturismo.
    • Total walking time: (approximately 3.5 hour, plus sightseeing time of 4-5 hours with extra option).
    Breakfast | Dinner

    Day 3 - San Gimignano

    • After breakfast, directly from the agriturismo, you will begin your walk to one of Tuscany's most treasured towns - San Gimignano.
    • You will make your way up along a ridge to the small hamlets of Ciuciano and San Donato, passing by several old 'pievi' (countryside churches) and villas and with wonderful views of the skyline of San Gimignano.
    • This town - sometimes referred to as having the only “skyscrapers” in Tuscany – is an absolute must, a magnificent medieval city with picturesque vineyards, olive and cypress groves surrounding it on all sides.
    • You will have time to explore this small romantic old town with its towers that remain from medieval times. The town once had 52 of these towers (there are now less than a dozen).
    • Wealthy, prominent families would use the height of these towers to distinguish themselves, and the towers also served to alert the inhabitants of approaching friends and foes.
    • A stroll along the town's impressive medieval town walls is a must. In the town itself there are numerous places to enjoy lunch.
    • You will then follow the Via Francigena back to your agriturismo. First you will pass the convent of Monte Oliveto, located on a wide ridge, before winding down to a small stream, which you will cross before you climb back up to the agriturismo where you'll spend another night.
    • You will have another chance tonight to sample something different from the sumptuous menu of the restaurant. (Total walking time: approximately 4 – 5 hours)
    Breakfast | Dinner

    Day 4 - Monteriggioni

    • Today you will bid farewell to the agriturismo and head for Monteriggioni, defined by Dante as a crown in the landscape.
    • The walk first takes you down into the river valley, before you follow the Foci and eventually reach one of the most wonderful Romanesque churches of Tuscany, la Badia a Conèo.
    • The next stop is Quartaia, followed by Gracciano, once one of the most important wheat towns of Tuscany. Another short stretch brings you to the Badia a Isola, once an important stop on the medieval Via Francigena, and a very intriguing building.
    • The final destination for today is Monteriggioni, where you'll have time for a drink in the square.
    • You will then be picked up by a taxi and transferred to Siena, where you settle in your centrally located hotel, just a few minutes away from the famous Piazza del Campo.
    • In the evening you can enjoy a nice stroll into town to have dinner in one of the town's many restaurants, or perhaps a drink in the Piazza del Campo.
    • (Total walking time: approximately 4-7 hours (4 hours for shorter options available), plus sightseeing time).

    Day 5 - Siena - San Quirico

    • A short train ride will take you from Siena to the medieval town of Buonconvento, enclosed inside 14th century city walls.
    • A great walk along the ‘strade bianche’ of the amazing Val d’Orcia takes through stunning Tuscan landscapes to the fortified medieval town San Quirico.
    • One of the most interesting towns of the Val d’Orcia, an impressive medieval wall has protected the town for centuries and today four gateways into the town remain.
    • The beautiful old town is home to a wonderfully restored Romanesque church and the 15th century Palazzo degli Amergihi.
    • San Quirico will be your base for the next two nights. From here you may wish to take an optional visit to the nearby town of Montalcino. (Walking time: approximately 5 -6 hrs).

    Day 6 - San Quirico - Bagno Vignoni or Pienza

    • Today you will have a choice of two great walks. The first option is a walk from San Quirico to the town of Bagno Vignoni; a unique ancient Roman spa town.
    • The town is renowned for its thermal healing waters and the main square or ‘piazza’ is a pool of steamy thermal water that is replenished from the village’s thermal springs.
    • The healing powers of the town’s thermal waters were first discovered in Etruscan times and later the Romans used the town for both health and relaxation purposes.
    • The second option today is a morning walk to the tiny town of Pienza. This town has an interesting history. The first concepts of Renaissance town planning where put into practice here, when Pope Pius II decided to transform the look of his birth town through the help of architect Bernardo Rossellio.
    • The beautiful Piazza Pio II and its surrounding structures is a perfect example of their vision.
    • There is plenty of time to explore Pienza and from here you may wish to take an optional visit of Montepulciano by bus.
    • This afternoon you take a local bus back to San Quirico, either from Pienza or Montepulciano (Walking time: approximately 3-5 hours).

    Day 7 - End San Quirico

    • Your trip will come to an end in San Quirico after breakfast. From San Quirico you can either take a bus to Siena (and from there a connecting bus to Florence) or you can take a bus to Montepulciani or Chiusi, and a connecting train to onward destinations in Italy.
  • What to Know

    What's Included

    • Luggage transfers
    • Detailed route notes and maps
    • Transfer from Torraccia di Chiusi to Siena
    • Accommodation (4 nights conformable hotel & 2 nights agriturismo)

    Not Included

    • International flights
    • Arrival and departure transfers
    • Departure taxes
    • Visas
    • Travel insurance (compulsory on all trips)
    • Lunches and dinners (unless otherwise stated in itinerary)
    • Drinks
    • Additional tours or activities
    • City tax in San Gimignano (every traveller to San Gimignano must pay a city tax of EUR 2.25 per person, per night. This must be paid at the hotel reception on check-in.)
    • Entrance fees
    • Taxis/transport (if opting out of walks)
    • Local bus and train tickets as part of program (allow EUR10 per person)
    • Tips
    • Items of a personal nature
  • Map Itinerary

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Trip at a glance

Trip Code PETU
Group size 2 - 16
Start City: Colle Val d'Elsa
End City: San Quirico
Style: Independent

What to know

This is a moderate walk which is suitable for those who have some experience with hiking/walking and those with a good general physical condition. You should be able to walk for up to 5 hours a day in hot sun and on dusty or stony tracks.

This is a self-guided walking tour and does not include the services of a tour guide and you will not be part of a group.

Departure dates

This trip operates daily from 01 March until 15 November.

Route Notes

At the joining hotel on Day 1 you will receive your detailed road book which includes a technical description of the itinerary, maps, contact listing and 24-hour emergency phone number, as well as useful information on each place visited.

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