Siena, the Val d’Orcia and Montepulciano feel like three chapters of the same story: a medieval city, big-sky hills and wine villages with views in every direction. Distances are short, so you can wake up in the countryside, spend a morning in Siena and be back in time for sunset over the vines.
Brick-red Skylines, Big-sky Hills & Noble Wines
For many ExpertoItaly travellers, this part of southern Tuscany becomes the quiet heart of a longer Italian journey – the chapter where the pace eases after Florence, Chianti or the coast, with long lunches, thermal baths, easy drives and evenings that end in small piazzas rather than big-city streets.
Who Siena & the southern hills suit best
✓ Couples who want a blend of city life, countryside and wine villages
✓ Travellers who enjoy walking ancient streets by day and quiet piazzas by night
✓ Food and wine lovers keen on Brunello, Vino Nobile and serious Tuscan cooking
✓ Drivers who like scenic routes, small towns and stopping whenever a view tempts them
Where to Stay in Siena, Val d’Orcia and Montepulciano
We favour small, characterful places with a sense of history and a genuine welcome. No two are the same; we will match you to the right one based on how you like to travel.
Palazzo del Capitano Wellness & Relais
Siena, Val d’Orcia & Montepulciano
A romantic 15th-century palazzo in San Quirico d’Orcia offering intimate rooms, secret gardens, and candlelit wellness spaces — perfect for couples and honeymooners.
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Fattoria Svetoni
Siena, Val d’Orcia & Montepulciano
Fattoria Svetoni offers couples a luxurious Tuscan retreat, with wine tastings, stunning views, and proximity to historic towns.
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Lupaia
Siena, Val d’Orcia & Montepulciano
A farmhouse with an impeccable style, with stone walls, ceilings with wooden beams, frescoed walls and elegant and refined furnishings.
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Castello Banfi
Siena, Val d’Orcia & Montepulciano
For the luxury traveler seeking the epitome of indulgence, Castello Banfi—Il Borgo offers the perfect blend of fine wine, exquisite cuisine, and serene relaxation.
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Montestigliano Estate
Siena, Val d’Orcia & Montepulciano
A unique collection of eleven high-quality apartments and farmhouses, on an exquisite Tuscan estate in the Senese hills, that is perfect for couples, families and group celebrations.
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Locanda San Francesco
Siena, Val d’Orcia & Montepulciano
A 4-bedroom boutique B & B in a 14th century palazzo overlooking Piazza San Francesco in the historic centre of Montepulciano.
DETAILSGetting Around
Best with a car…
…but car-free is still possible
For this region, a car is usually the most comfortable way to travel. Distances are short but public transport is patchy once you leave the main rail lines, and the joy of the area lies in the viewpoints, villages and vineyards between the obvious stops. We arrange car hire from Florence, Pisa or Rome and provide clear, simple route ideas rather than complicated daily schedules.
If you prefer not to drive at all, it is still possible to enjoy Siena and selected Val d’Orcia or Montepulciano bases using a mix of trains, local taxis and private drivers. In that case, we will steer you towards locations where car-free logistics genuinely work and build transfers into the itinerary from the start, rather than as an afterthought.
Is this your Tuscany heartland?
Where exactly are Siena, Val d’Orcia & Montepulciano?
They sit in southern Tuscany, with Siena as the medieval city hub and the Val d’Orcia and Montepulciano spread across the hills to the south and east – an easy, compact area to combine in one stay.
Why include all three in one holiday?
Together they give you the full southern Tuscany picture: Siena for city life and Gothic drama, the Val d’Orcia for big-sky landscapes and hot springs, and Montepulciano for hilltown atmosphere and noble wines.
How long should I stay in this area?
Four to six nights is a comfortable minimum; a week lets you enjoy Siena, two or three hilltowns, a winery or two, a thermal soak and some slower, view-filled drives.
Do I need a car for Siena, Val d’Orcia & Montepulciano?
Siena itself works car-free, but a car (or planned drivers) makes the surrounding hills far easier, as the best viewpoints, villages and vineyards sit between the main public transport routes.
When is the best time to visit this part of Tuscany?
April to June and September to mid-October are ideal for light, views and walking. Summer is hotter and livelier in the villages; winter is quieter and more contemplative, with a softer, slower rhythm.
Siena & Val d’Orcia travel guides
Want to read more before you decide? These pieces dive deeper into Siena, the Val d’Orcia and Montepulciano.
Tailor-made Siena, Val d’Orcia & Montepulciano by ExpertoItaly
Let southern Tuscany be the quiet heart of your Italian journey
Picture Siena’s brick-red skyline, the soft curves of the Val d’Orcia and Montepulciano’s wine-soaked lanes, all threaded together in one unhurried chapter rather than scattered day trips.
Tell us how you like to travel – more city, more countryside, more wine, or a little of everything – and we will shape this corner of southern Tuscany around you, with driving, trains and drivers planned so it feels effortless rather than remote.
More Tuscan bases to mix and match
Tuscany works best as a gentle multi-centre. Explore our other favourite areas below – you can
combine any of them in one tailor-made holiday, with travel and timings stitched neatly together
for you.
Florence
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Clients often mention what matters most — care, precision, and the sense of travelling with someone who knows the way.
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