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Southern Tuscany – 5 nights
Renaissance hilltop towns and classic wines
Back to Routes
Tuscany
Piazza del Campo, Siena
Rolling hills and cypress trees
Siena Cathedral
Valley below Pienza
Ripa
San Biagio
Tuscany cypresses
Montepulciano wine
Looking towards Montalcino
Tuscan road
The reward for climbing up to the hilltop towns!
Abbazia di Sant' Antimo
A typical walk in Tuscany
At a glance
5 nights (4 days walking) - miss Siena (start in Buonconvento) and spend just one night in Montalcino (miss Sant' Antimo walk).
How much walking?
Full days: 14 -19 km per day, 4¼ - 6 hrs walking
Using shortening options: 9-14km per day, 3-4 hrs (using lifts)
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. This version starts in rural Buonconvento, through Montalcino, Bagno Vignoni and its ancient thermal baths, Pienza and a final walk up from the church of San Biagio to the cathedral at Montepulciano.
Walked by On Foot staff: Simon, Debbie and Harriet
REVIEWS: For independent walker reviews submitted to the Association of Independent Tour Operators visit Aito.com.
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
- 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
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?
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. Highest point on route: 600m.
Medium: Average cumulative uphill stretches (CUSs) 592m (170m-760m) per day.
Easy-medium: CUSs 347m (480m – 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
Itinerary
Day 1 - Arrive in Buonconvento
Arrive in Buonconvento by train, (and be met by the hotel driver); and enjoy your first night looking over the Tuscan countryside.
Day 2 - 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 3 - 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 4 - 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 5 - 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
ARRIVING BY AIR
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.
ARRIVING BY TRAIN
Nearest railway station:
Start: 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 thetrainline.com for times, ticket booking and other information.
ARRIVING BY CAR
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.
PISA AIRPORT
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.
FLORENCE AIRPORT
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.
Night 1
Buonconvento – Pieve a Salti (dinner, B&B)
Restaurant with rooms (and pool) in a lovely position.
Night 2 (Upgrade)
Montalcino – Vecchia Oliviera (B&B)
Tastefully decorated, cool and airy, just outside old town, with pool.
Night 4
Pienza – Piccolo Hotel la Valle (B&B)
Gloriously positioned and comfortable hotel just outside the old town.
Night 4 (Upgrade)
Former Franciscan convent near the Cathedral, converted into slightly faded hotel with panoramic terrace. Choose a room with view over the Valle d'Orcia.
Night 5
Montepulciano – Meuble il Riccio (B&B)
Delightful B&B in the old town. Opportunity to upgrade to superior rooms.
Buonconvento – Pieve a Salti (dinner, B&B)
Restaurant with rooms (and pool) in a lovely position.
Website
Montalcino – Vecchia Oliviera (B&B)
Tastefully decorated, cool and airy, just outside old town, with pool.
Website
Bagno Vignoni – Hotel le Terme (dinner, B&B)
Recently refurbished hotel overlooking the original thermal pool, with own pool/spa.
Website
Pienza – Piccolo Hotel la Valle (B&B)
Gloriously positioned and comfortable hotel just outside the old town.
Website
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.
Website
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!
Prices
Total 5 nights in double/twin room, all breakfasts, one evening meal, 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 £180
Lone Traveller Additional Supplement (LTAS): from £140
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 £15 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)
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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