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Southern Tuscany

  • 7 Night Route

    Price: from £1065
  • 6 Night Route

    Price: from £950
  • 5 Night Route

    Price: from £865
  • 4 Night Route

    Price: from £750

Renaissance hilltop towns and classic wines

Back to Routes
Tuscan hills

Tuscan hills

Piazza del Campo, Siena

Piazza del Campo, Siena

Classic Tuscany

Classic Tuscany

Siena Cathedral

Siena Cathedral

Valley below Pienza

Valley below Pienza



San Biagio

San Biagio

Tuscany cypresses

Tuscany cypresses

Montepulciano wine

Montepulciano wine

The reward for climbing up to the hilltop towns!

The reward for climbing up to the hilltop towns!

Looking towards Montalcino

Looking towards Montalcino

Abbazia di Sant' Antimo

Abbazia di Sant' Antimo

A typical walk in Tuscany

A typical walk in Tuscany

The baths at Bagno Vignoni

The baths at Bagno Vignoni

  • 7 Night Route

    Price: from £1065
  • 6 Night Route

    Price: from £950
  • 5 Night Route

    Price: from £865
  • 4 Night Route

    Price: from £750
Price: from £1065
Nights: 7
Walk: 3½ - 6 hr/day

This was the first time my husband and I did anything like this for a vacation. We had no idea what to expect. We were both completely amazed by the details of everything! Shuttle picked us up on time for Monte Oliveto and she was so nice! Our suitcases were at each hotel waiting for us when we arrived at each place. Everything was figured out for us- you gave us an incredible vacation and we’re so appreciative!!

J White, Vermont, USA - May 2024

So well planned and arrangements were carried out to perfection. The suitcase fairy magically getting our bags from a hotel lobby in the morning to our room before we arrive in the afternoon. The walking exceeded our expectations - all beautiful, well-planned routes with enough variety to keep it interesting.

Mary Long, Silver Spring, USA - April 2024

We loved everything about our trip. We wanted to see and experience everything. We also took every suggested detour and explored every suggested landmark, which made our walks sometimes even longer and more challenging for us, but then again, we just didn't want to miss a thing.

Theresa and Anival Morales, CA, USA - October 2023

The info packet was hugely appreciated! We were curious as to why you needed so much info from us up front but then we were very impressed that you went the extra mile and gave us bus and train timetables, suggested taxi services and even restaurant recommendations for the days on either side of our On Foot itinerary. Quite frankly, it made us feel as if you cared :)

Elizabeth Kelly, Ossining, USA - October 2023

This is our second On Foot holiday after Naxos and Amorgos. We deliberately planned it with stops in different towns and this made it feel like a real holiday. We really loved all the hill towns and the food was wonderful.

Anne Ladd, Derbyshire, UK - September 2023

Very much enjoyed our holiday - having been on several previous hikes (Priorat, Andalucia, Cornwall, etc), Tuscany presented an entirely different dynamic - far less dramatic - rustica distilled.

Michael Murphy, Florida, USA - September 2023

As ever - excellent, very patient in getting the right hotels and routes booked. The office always responds quickly to any requests and follows up - the person may change but everyone seems able to pick up where previous conversations have got to. Fi very patiently helped me load the phone app - despite my terrible IT skills.

Jane Parker, Leyland, UK - June 2023

Before leaving, my husband and I had trepidations about following the walking directions - we tend to get lost! We are happy to report that after we became acclimatised to understanding the written directions we found them to be spot on and we were able to enjoy the walks each day without worrying too much that we were off the track.

We really appreciated having the knowledge that Danielle was available if we ran into any issues along the way, grateful that we did not need to contact him, but it gave us a peace of mind. It is hard to decide what we liked best, we loved the walking routes, and scenery along the way. Our accommodations were what we expected based on your descriptions of each. It was really nice to know that our luggage would meet us at the end of the day!

Andrea Martin, Lititz, USA - May 2023

The beauty of the hiking of Tuscany was never ending. We loved all the villages but really fell in love with Pienza.

In Pienza we ate at a very good restaurant called Sperone Nudo. We had the most fantastic pistachio tiramisu we've ever had in our lives!!!

Cathleen Zoss, Fort Collins, USA - April 2023

It was my first experience of a self-guided walk alone, and a week back I am still on a high. The wonderful weather certainly helped.

The advice, if I was lost to go back to where I knew I was in the right place, was good. Luckily it only happened once!!

Jo Sanderson, Richmond, UK - May 2022

More independent feedback
A self-guided walking holiday in southern Tuscany with On Foot Holidays

At a glance

7 nights (6 days walking) - the full route. Extra nights recommended in Siena, Pienza and Montepulciano and others. See 'Prices' tab for what's included.
Suggested route pairing: Umbria, Ligurian Hills, Amalfi Coast, Lake Maggiore, Slovenia

How much walking?

Full days: 11-19 km per day, 3½-6 hrs walking
Using shortening options: 9-14km per day, 3-4 hrs (using lifts)

Max. Grade:

Southern Tuscany - Renaissance hilltop towns and classic wines

The Tuscan landscape at its most evocative – exposed rolling hills crossed by the ubiquitous ‘white roads’ and protected by dramatic hilltop villages, whose very stones reek of medieval power struggles and intrigue. And to assist in the consideration of these issues, two fine red wines, the rich Brunello di Montalcino and the Vino Nobile di Montepulciano, with their vineyards at the heart of our walk. From Siena, pass through Montalcino, the Abbey of Sant’ Antimo, Bagno Vignoni and its ancient thermal baths, historic Pienza and a final walk up from the church of San Biagio to the cathedral at Montepulciano. We recommend extra nights in most places to explore the treasures of these towns as well as to relax and to eat and drink well.

Do be aware that unlike many of our other routes, in Tuscany shortening or missing days using taxis is generally not possible – there is a scarcity of taxi drivers, and those that are available tend to charge highly for their services, even for very short journeys.

Walked by On Foot staff: Simon, Debbie, Harriet and Patrick

Consider pairing this route with Umbria (2½ hrs by taxi and train), Ligurian Hills (7 hrs by taxi and train), Amalfi Coast (6-7 hrs by taxi, train and ferry), Lake Maggiore (7 hrs by taxi, train and ferry, recommended overnight stop in Milan), Slovenia (6½ hrs by train, recommended overnight stop in Venice or Florence) – for more details click here.

REVIEWS: For independent walker reviews submitted to the Association of Independent Tour Operators visit

TRAVEL ADVICE: To find the latest travel advice from the Foreign & Commonwealth Office for UK citizens travelling to Italy, click here. Citizens of other nations will also find it useful, but should always check their appropriate local agency.

Route Highlights

  • Siena, the Campo and cathedral
  • The rolling hills of Southern Tuscany
  • Pienza, the classic Renaissance hilltop town
  • Montepulciano, San Biagio and the cathedral
  • Brunello di Montalcino

This route features the following characteristics and interests: Villages and farms, Art, History, Wine

Things you should know

  • This route is less about the walking than about the historical, picture-perfect hilltop towns that you stay in. Stride out along the tracks through the iconic Tuscan landscape.

We Recommend

An extra night in Siena at the start to explore this historic and beautiful city, extra nights at Pienza or Montepulciano (both classic hilltop towns), at Bagno Vignoni to take the waters, or at Buonconvento to relax, swim in the pool and watch the sunset over the Tuscan hills.

Wine tasting at one of the Enotecas in Montalcino or Montepulciano (we offer some suggestions - your hosts can also advise).

Eating and Drinking

Tuscany can be very sophisticated and it is sometimes difficult to find an authentic regional dish, though Leonardo at Pieve a Salti thinks differently – “all our food is grown on our farm if at all possible – we have the largest organic farm in the region.  My favourite dishes here are Penne con ragù di Cinta (pork ragout) or Pici with ragù all’aglione (tomato and garlic ragout), Zuppa di farro (spelt soup), Cinghiale in umido (wild boar), Rasato al Brunello (veal with Brunello Wine) – all of which are Tuscan specialities.  And of course you must have some wine – Brunello di Montalcino – the vineyards are just down the road!”

How much Walking?

Full days: 11-19 km per day, 3½-6 hrs walking
Using shortening options: 9-14km per day, 3-4 hrs (using lifts)

Getting up to the hilltop towns at the end of each day always makes it seem harder! Walking mainly on tracks, sometimes called ‘white roads’. Shortening or missing days using taxis is generally not possible.

Highest point on route: 600m.

Medium: Average cumulative uphill stretches (CUSs) 480m (170m-760m) per day.
Easy-medium: CUSs 347m (170m – 510m) using shortening options if available.

Acrophobia/vertigo warnings: None.

GPX file available for handheld GPS or smartphone App for complete route.

Important note: Times given for each day are  walking times for an “average” walker and exclude stops.  “CUSs” stands for “Cumulative Uphill Stretches” and measures the aggregated ascents in each day, expressed in metres of climb.  See “Walk Grading” for more information.

When to go?

The best months to walk: April, May, June, mid September onwards, October

Other possible months: July, August, November

The variety of tracks in the beautiful Tuscan landscape give good walking at any time during our suggested season, but particularly in late spring with its wide open views. Early September can be dry but later and into October much greener after the post-summer rains and the approach of autumn colours.

Start Dates


Weather Chart


Temperature and rainfall chart for Southern Tuscany


About the Route

Day 1 - Arrive in Siena

Arrive in Siena. If only an evening is allowed to you, we suggest a good wander, down to the Campo (where the famous annual Palio horse race is held, with attendant flag bearers and drummers) and the cathedral, envelop yourself in the magic of this historic town, and eat well in one of many possible restaurants.

Day 2 - Monte Oliveto to Buonconvento (Pieve a Salti)

Short taxi transfer included. After a look at the frescoes in the cloister at the Abbey of Monte Oliveto Maggiore, a short but sharp start to your walking takes you via (we suggest) lunch in one of Chiusure’s little restaurants, to your first taste of the Tuscan landscape and a little luxury at the hilltop country hotel of Pieve a Salti, with its views from the terrace and a plunge in the pool. (Medium: 4 hrs walking (allow 5¼ hrs), 11 km (7 miles), CUSs 340m)

Day 3 - Buonconvento to Montalcino

A gentle amble on the wide ridge road until you strike south across the cornfields along old tracks up and down the Tuscan countryside, with splendid views on the way to your first real climb – 300m or so up to the citadel of Montalcino. (Medium-hard: 5 hrs walking (allow 6¾ hrs), 15½ km (10 miles), CUSs 760m)

Day 4 - Montalcino to Sant’ Antimo

The easy day. Almost entirely downhill, through the vineyards around Montalcino onto the plateau land above the Villa a Tolli before you light upon the lovely Cistercian Abbey of Sant’ Antimo in its valley setting, and maybe lunch before the bus home (not Sunday – when you could retrace your steps or organise an (expensive) taxi). (Easy: 3½ hrs walking (allow 4¾ hrs), 11 km (7 miles), CUSs 170m)

Day 5 - Montalcino to Bagno Vignoni

Drop down from Montalcino to the fertile farmland below, and further to the sleepy meadows of the Asso valley and its occasionally exciting river fording. Finally, a walk in along the Orcia valley to your next accommodation near the ancient baths at Vignoni. (Upgrade to a spa hotel adjacent to the baths, and perhaps stay an extra night to enjoy the spa all day – admission included in the upgrade price!) (Medium-hard: 6 hrs walking (allow 8 hrs), 19 km (12 miles), CUSs 520m)

Day 6 - Bagno Vignoni to Pienza

Start off up the hill to the delightful hamlet of Vignone, with its great view of Rocca d’Orcia on the other side of the Orcia valley, and then down to San Quirico, an unassuming yet attractive town with a fine medieval core – time for a coffee (or lunch if you start late!). Then a ramble across typical Tuscan rolling fields to the best hilltop town of them all, and a world heritage site – Pienza. (Medium: 4¼ hrs walking (allow 5¾ hrs), 14 km (9 miles), CUSs 610m).

Day 7 - Pienza to Montepulciano

For your last day, a walk across the pretty countryside east of Pienza to little Monticchiello, and perhaps a coffee stop. Afterwards, navigate through woodlands and up onto the ridge again for a great approach to Montepulciano via the extravagant temple of San Biagio, before climbing the infamous Montepulciano ramp to the cathedral square and your triumphant finale. (Medium: 4½ hrs walking (allow 6 hrs), 14 km (9 miles), CUSs 480m)

Departure day

Depart for home (or choose to stay further nights)

Travel Information


Nearest railway station:
Siena (unless starting in either Buonconvento or Montalcino, in which case Buonconvento)
Finish:  Chiusi-Chianciano Terme (rarely, oddly enough, Montepulciano)

Sample journey by rail:
Via Rome: Rome to Florence, Florence to Siena ~3½ hrs
Chiusi-Chianciano Terme to Rome: ~2 hrs direct

We suggest for times, ticket booking and other information.


Not ideal (unless your first night is in Montalcino), but best is to drive to Montalcino and park in a public car park there (supplement). Taxi to your first night and back at the end.


The best ‘local’ airports are Pisa and Florence.  Intercontinental flights use Rome. Flight information can change rapidly and not all flights run daily.

Land by: 17:30 (Pisa or Florence) for public transport connections to Siena (15:30 if starting at Buonconvento or Montalcino)

Return flight earliest: 13:30 (Florence), 15:00 (Pisa). Earlier flights possible missing breakfast, alternatively overnight in Florence/Pisa.

Flight information can change rapidly and not all flights run daily. Please do check directly with the airlines’ websites or Skyscanner (see below) before finalising any booking with us. Do not book your flights until we have confirmed that we have provisionally reserved accommodation for you.

For up-to-date schedules and flights from all airports check Skyscanner.

See “Getting to the start of your walk” below for transfer information.


Getting to the start of the walk

The first hotel is in Siena, Buonconvento or Montalcino, and the last in Montepulciano.  Transfer times and methods are suggested from Pisa airport below.


Outward: Two buses or train + bus, change in Florence.  Allow ~3½ hrs from touchdown in Pisa to arrival in Siena.

Return: Bus to Chiusi-Chianciano Terme, then train from there via change in Florence to Pisa Centrale, change on to shuttle train to Pisa airport. Allow ~4hrs.


Outward: Shuttle bus to centre, then bus to Siena ~2hrs

Return: Bus to Chiusi-Chianciano Terme, then train to Florence and shuttle bus to airport ~3hrs

Full transfer advice, including timetables, is provided in your Walkers’ Pack. Contact us if you would like additional pre-booking information.

Where You'll Stay

This route offers a range of hotels.  Our standard options include a little B&B in central Siena (sadly often full), a countryside restaurant with great views and excellent rooms, two typical authentic Italian ones, a little one at the edge of Pienza old town with fantastic views, and a quirky one in Montepulciano with rooftop terrace (in season). Upgrades can include historic buildings (Siena), smart international (Montalcino), a former monastery (Pienza) and rooms with a view (in our standard Montepulciano B&B).  Take your pick!  You might also like to consider Montalcino’s Dei Capitani (one of our alternative hotels) and its pool if booking for late June, July or early September.

Siena – Al Mercato (B&B)

Night 1

Siena – Al Mercato (B&B)

Welcoming B&B very near the Campo.

Siena – Palazzo Ravizza (B&B)

Night 1 (Upgrade)

Siena – Palazzo Ravizza (B&B)

Gorgeously restored 19th century palazzo with in-keeping furnishings. Beautiful panoramic garden.

Buonconvento – Pieve a Salti (dinner, B&B)

Night 2

Buonconvento – Pieve a Salti (dinner, B&B)

Restaurant with rooms (and pool) in a lovely position.

Montalcino – Il Giglio (B&B)

Night 3 & 4

Montalcino – Il Giglio (B&B)

Family run hotel with excellent restaurant.

Montalcino – Vecchia Oliviera (B&B)

Night 3 & 4 (Upgrade)

Montalcino – Vecchia Oliviera (B&B)

Tastefully decorated, cool and airy, just outside old town, with pool.

Pienza – Piccolo Hotel la Valle (B&B)

Night 6

Pienza – Piccolo Hotel la Valle (B&B)

Gloriously positioned and comfortable hotel just outside the old town.

Pienza – Il Chiostro (B&B)

Night 6 (Upgrade)

Pienza – Il Chiostro (B&B)

Former Franciscan convent near the Cathedral, converted into slightly faded hotel with panoramic terrace. Choose a room with view over the Valle d'Orcia.

Montepulciano – Meuble il Riccio (B&B)

Night 7

Montepulciano – Meuble il Riccio (B&B)

Delightful B&B in the old town. Opportunity to upgrade to superior rooms.


Price: from £1065 for 7 nights

Total 7 nights in double/twin room, all breakfasts, 1 evening meal, 1 picnic, taxi from Siena to start of walk, luggage transfers between all hotels on walking route; full Walkers Pack with route directions, maps, transfer and background information; local telephone support.

Locally levied tourist taxes are not included.

All prices are per person unless otherwise indicated, and are based on a standard booking in May. Prices may vary seasonally and a fixed price will be given to you before you commit.

Single Room Supplement (SRS): From £295
Lone Traveller Additional Supplement (LTAS): From £255
Large Party Saving (LPS): Groups of more than 2 people (on an identical itinerary, on the same booking and booked at the same time) –  discount of at least £40 per person
Maximum party size: 10


Add Ons

Additional nights or upgrade hotels: Contact On Foot Holidays for prices (vary with season)
Sending Walkers Packs to addresses outside the UK:  £20-£60 (per pack, location dependent)

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Daniele Cavazzoni (Southern Tuscany)

Our local team

Daniele Cavazzoni (Southern Tuscany)

Daniele's early passion for nature led him to explore all the Italian regions on foot. He started working as a nature guide for an international tour operator, working around the Indian Ocean and in the African savannah.

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