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Southern Tuscany

  • 7 Night Route

    Price: from £900
  • 6 Night Route

    Price: from £805
  • 5 Night Route

    Price: from £725
  • 4 Night Route

    Price: from £650

Renaissance hilltop towns and classic wines

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Piazza del Campo, Siena

Piazza del Campo, Siena

Rolling hills and cypress trees

Rolling hills and cypress trees

Siena Cathedral

Siena Cathedral

Valley below Pienza

Valley below Pienza



San Biagio

San Biagio

Tuscany cypresses

Tuscany cypresses

Montepulciano wine

Montepulciano wine

Looking towards Montalcino

Looking towards Montalcino

Tuscan road

Tuscan road

The reward for climbing up to the hilltop towns!

The reward for climbing up to the hilltop towns!

Abbazia di Sant' Antimo

Abbazia di Sant' Antimo

A typical walk in Tuscany

A typical walk in Tuscany

Price: from £900
Nights: 7
Walk: 3½ - 6 hr/day

Travellers Blog

Tuscany – Leonardo da Vinci’s inspiration

Tuesday 2nd April | Posted by On Foot Staff

Tuscany – Leonardo da Vinci’s inspiration view article

Customer Feedback

Heather Amsden

"We like to hike. We liked the idea of being self-guided instead of with a group. But, until we found On Foot, it seemed too daunting to us to try to plan a hike in a foreign country. We needed On Foot's support and concierge services to take our dream and turn it into a wonderful, relaxing, luxurious vacation." October 2019

more testimonials

What a delight to have some solitude in that beautiful countryside. I cannot overstate how all four of the hotels exceeded our expectations. The trails were fantastic and the AlpineQuest app and the instructions for its use were VERY helpful. We used the app - in combination with the written instructions - the entire time.

Lastly, the entire booking process - starting with my questions to determine which vacation to take - was so smooth. Everyone at On Foot was incredibly professional and helpful and friendly. Thank you!

Heather Amsden, Newton, USA - September 2019

We loved so many things about this holiday - the walking was exactly as we anticipated (although we might have liked one or two more challenging days), on quiet tracks with amazing scenery and good weather. We loved exploring the different towns we stayed at, and getting to eat good food and taste some nice wine.

We knew from past experience that On Foot could arrange a great holiday for us.

Tamsin James, London, UK - August 2019

Loved walking across white dusty roads in beautiful roaming hills, often not meeting anyone.

The choice of amount of days to walk was very useful. Your website was one of the best, detailing how to get to start and finish.

Patrick McGowan, Hartlepool, UK - June 2019

This was without question one of the most enjoyable trips that we have undertaken. Everything worked perfectly and the accommodation was good to excellent in all respects.

We seemed to pick the perfect eight days in the calendar as the wild flowers were everywhere and the birds greeted us wherever we went.

Roderic and Liz Mather, Skipton, UK - May 2019

I felt this holiday was worth every penny! The B&Bs were just superb and the Tuscany countryside was green, peaceful and alluring.

I so anticipated the Tuscany food and wine at every dinner. The restaurant suggestions were spot-on. Tuscany was all I had anticipated and more.

Dan and Gail Deyling, USA - April 2019

The scenery was spectacular, like walking through a painting. We liked being on our own and going at our own pace. We loved the serenity.

We enjoyed staying in the beautiful hilltop towns each night and being able to look down and see where we would be walking tomorrow.

Judith Hitchcock, Dudley, Australia - April 2019

Everything was fabulous! The trails were beautiful, lodgings were great. The food was amazing the whole trip. Everything went smoothly and pretty much according to plan. We appreciated how much English was spoken, since we speak NO Italian! Our only complaint is that we wished we could have stayed longer.

Absolutely the best vacation we've ever had. The trip of a lifetime! We were drawn to the opportunity to see places that most tourists don't see and enjoy a little bit of the 'real' Tuscany, away from crowds. We were not disappointed!

Gary Hopkins, Alpine, USA - April 2019

One of the best holidays we have ever had.

Friendly people we met on the way (some on holiday with your competitors who were envious of the level of service you provide) and locals were delightful. Food in Italy is wonderful, though not all the restaurants are! Great wines in this region, only sorry not to be able to carry it home. Weather was perfect, and April/May definitely the time to go. We would have struggled had it been much hotter. We are already looking at our next On Foot holiday.

Mark and Sarah Butt, Beccles, UK - May 2017

I enjoyed Tuscany, so beautiful, the mixed weather added to the dramatic views.

I really enjoyed having the extra day or two (our choice) at each place to be able to explore the area and relax. It was great not having to pack each night. All hosts were good as we have come to expect from On Foot. The differences in the types of accommodation is good and adds to the holiday experience. We passed several agritourism places and it might have been good to stay in some more of those and enjoy evening meals as we did in Slovenia. Although on saying that, I think this has been my favourite On Foot holiday so far. The wild boar piglet crossing the road in front of us was very special.

Sue Garden, Brentford, UK

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.

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 – rolling hills 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, 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.

Walked by On Foot staff: Simon, Debbie and Harriet

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.

COVID-19 SAFETY PRECAUTIONS: Please read our summary of current regulations.

Route Highlights

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

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

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’. 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

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, September, 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.

Use the calendar below to see in more detail the best times to walk.

Please note: date ranges shown are for a ‘normal’ year. While Covid-19 restrictions remain, please contact us to discuss your plans and availability.

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 (and more), a short but sharp start to your holiday takes you from the Abbey of Monte Oliveto Maggiore 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. (Easy-medium: 4 hrs, 11 km, CUSs 340m)

Day 3 - Buonconvento to Montalcino

A gentle amble along 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: 5½ hrs, 17 km, CUSs 760m, or take a taxi to start halfway easy-medium: 3 hrs, 9km, CUSs 510m)

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. (Easy: 3½ hrs, 11 km, 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, 19 km, CUSs 520m, or medium: 4 hrs, 14km, CUSs 400m with lift)

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, 14 km, CUSs 610m or easy-medium: 3¼ hrs, 10km, CUSs 365m with lift).

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, 14 km, CUSs 480m, or easy-medium 3 hrs, 9 km, CUSs 300m with lift)

Departure day

Depart for home (or choose to stay further nights)

Travel Information


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.


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

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.


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, 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 smart international (Montalcino), a former monastery (Pienza) and ultra-smart boutique (Montepulciano).  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.

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.

Staying in Rome

We think we have one of the best and most reasonably priced places to stay in Rome – Roberta’s B&B Orologio. In a narrow street between the Piazza Navona and the Vatican, Roberta has been our Rome host for the last ten years and has never let us down.  With her stylish charm and attention to detail she ensures that if you return to Rome you will stay there again.  And has opened another B&B nearby just in case she is full!


Price: from £900 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 £250
Lone Traveller Additional Supplement (LTAS): From £190
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 £35 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:  £10-£40 (per pack, location dependent)

Travellers Blog

Tuscany – Leonardo da Vinci’s inspiration

Tuesday 2nd April | Posted by On Foot Staff

Tuscany – Leonardo da Vinci’s inspiration view article

Customer Feedback

Heather Amsden

"We like to hike. We liked the idea of being self-guided instead of with a group. But, until we found On Foot, it seemed too daunting to us to try to plan a hike in a foreign country. We needed On Foot's support and concierge services to take our dream and turn it into a wonderful, relaxing, luxurious vacation." October 2019

more testimonials
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Daniele Cavazzoni

Our local team

Daniele Cavazzoni

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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