Stroll
Tuscany in Depth: Volterra to Montepulciano - 11 Days
ItalyTuscany

Tuscany in Depth: Volterra to Montepulciano - 11 Days

11 Days
Moderate

Tuscany in Depth: Volterra to Montepulciano - 11 Days

from £1,805 / person

Overview

This walk explores Tuscany from the ancient city of Volterra, via the medieval powerhouse of Siena and the hilltop town of San Gimignano, before crossing the UNESCO-protected Val d'Orcia region to the elegant hilltop town of Montepulciano. The route follows sections of the ancient Via Francigena deep into a landscape of soft rolling hills and avenues of towering cypress trees.

The walk takes in the 16th-century wine town of Montalcino, renowned for its Brunello wine, and the remarkable thermal baths of Bagno Vignoni, where hot springs have drawn visitors since Roman times. The route moves through chestnut groves, vineyards and classic Tuscan countryside, passing the hilltop hamlets of Castelnuovo dell'Abate and Monticchiello along the way.

Highlights

  • Walk from Volterra, via Sienna through Tuscany's Val d'Orcia region, to Montepulciano
  • Hang out in the glorious 'Piazza del Campo' in Siena and in the hilltop town of San Gimignano
  • Sample the award-winning Brunello wines of Montalcino
  • Soak in the thermal baths of Bagno Vignoni
  • Visit medieval abbeys, hilltop towers and Romanesque churches
  • Explore the Renaissance town of Montepulciano
  • Spend each night in classic Tuscan townhouses or rural hotels

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What's Included

Accommodation

3-star Hotel (9 nights), B&B (1 night)

Transfers

  • Private Vehicle Transfers
  • Luggage Transfers

Meals

10 breakfasts

Guidance & Support

  • Itinerary & Walk Notes
  • Walking App for Navigation
  • 24/7 on-trip support

How We Rate This Walk

3

Stroll Walking Grade

Moderate

Rated by our team — we walk every route before we recommend it.

Expect some hills and longer walking days. A reasonable level of fitness will help you enjoy the experience.

View Fitness Guide

9

Days on the trail

12-21 km

Average per walking day

251-655 m

Gain per day

5/10

Trail difficulty

Where You'll Stay

During this walk, you will stay in a mix of small, family-run boutique B&Bs and three and four-star hotels, each one well placed along the route and well used to receiving walkers. As many overnight stops are in small villages and towns, alternative accommodation of equivalent standard may occasionally be necessary, and any such options will be discussed when your trip is confirmed. For those looking to make the most of the Chianti region, an upgrade to a wine resort in Gaiole in Chianti is available on request.

What You'll Eat

Each of the ten mornings begins with breakfast before you head out on the trail. Lunch is available at cafes and local food stores along the route, and your hosts will provide a list of dinner recommendations each evening to point you in the right direction. This stretch of Tuscany is one of Italy's great food regions, and eating well here requires very little effort.

Note: Please advise us of any food allergies or intolerances at the time of booking. If you have severe allergies, bringing some of your own snacks is recommended, as specialist ingredients can be harder to source along the way.

More About This Trip

The walk starts in Volterra and finishes in Montepulciano, in the heart of Tuscany. Three airports serve the start of the walk. Florence (FLR) is the most convenient, with a direct train to Siena taking around 2 hours, from where buses connect to Volterra. Pisa (PSA) is a well-connected alternative; the Pisa Mover shuttle connects the airport to Pisa Centrale, from where trains reach Siena in around 1 hour 30 minutes to 2 hours. Rome Fiumicino (FCO) is a further option, with trains reaching Siena in around 2 hours 30 minutes via Rome Centrale. Private transfers from Siena to Volterra can be arranged on request. Book Italian rail tickets in advance through Trenitalia.

The walk ends in Montepulciano. The nearest stations are Montepulciano Stazione, around 10 minutes by car, and Chiusi Chianciano Terme, around 30 minutes by car, which offers more frequent services. Remember to stamp your ticket at the platform machine before boarding any train in Italy.

This walk is available from 1 April to 31 October, but does not operate from 1 July to 22 August, when the Tuscan heat makes sustained walking uncomfortable. April and May bring warm, sunny days and pleasant evenings, with the countryside at its most colourful. June is a particularly beautiful month, with sunflowers in full bloom, vineyards in flower and long, warm evenings perfect for dining in the village piazzas. From late August, the heat eases and the grape harvest begins, bringing a lively, festive atmosphere to the villages. October is a fine month to walk, with warm days, cooling evenings and the Tuscan landscape turning gold. Thunderstorms are possible throughout the summer months, so a light waterproof is always worth packing.

This walk is graded moderate. Daily walks average 16.2 kilometres with around 453 metres of ascent and descent, and a terrain difficulty rating of 2 out of 10. Trails are well-defined and varied, taking in forest paths, gravel tracks, rolling farmland, vineyards, and village streets. Expect the occasional short steep section, rough surface, and steps. As is common throughout Italy, dedicated footpaths are not always available, so some road walking is unavoidable. Please remain mindful of other road users at all times. Good walking boots are recommended.

An exercise regime of two to three times per week, in addition to regular walking, is sufficient preparation. Daily walk notes, maps, and GPX tracks are provided.

Travel insurance is required for all Stroll walking holidays, covering cancellation costs, loss of luggage and injury. For international trips, your policy must also include medical evacuation coverage. A cancellation fee applies if you cancel after your holiday has been confirmed.

Dates & Pricing

Choose Your Start Date

Pick any available date — this is your trip, your schedule

August 2026

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Prices shown are per person, twin/double share basis.

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Frequently Asked Questions

As some of the walks on this itinerary are loop walks you can relax in the grounds of your accommodation (some of which have a pool) or explore the local town and its wineries. On the days where you will be walking to the next town, it might be possible to travel with the taxi service which transports your luggage. You can also use the local bus service between towns. Your accommodation hosts will have up to date information and advice should you wish to travel to the next destination by local transport. There is always plenty of information about options for the day in your daily walk notes and as always, you can call us at the office for help during your walk should you need any assistance.

SIENA - An incredibly well-preserved city with the show stopping Piazza del Campo at the heart of Sienese life. It is also possible to take a short bus journey to the hilltop towers of San Gimignano (an hour journey, or private transfers can be quoted and arranged).

Of course, please let us know at the time of booking if you would like to extend your time in Montepulciano. There is so much to see, we’d suggest at least 1 extra night.

We don't allow under 16's to do this walk. No discounts can be offered for children who do book.

Triple rooms can be difficult to book. Many accommodations don’t always offer them but we can offer a twin/double together with a single room.

You can start this tour by taking the train on day 1 direct from Siena to Buonconvento or Montalcino. This would reduce the trip to 7 or 6 days. Alternatively, we can discuss booking an additional taxi transfer for you to omit any 1 of the walks.

Of course, you may want to start by looking at our Tuscan Explorer which is 10 days and 9 nights, starting in Florence and ending in southern wine town of Montepulciano.

Of course, please let us know at the time of booking if you would like to extend your time in Siena. There is so much to see, we’d suggest at least 1 extra night.

Your main luggage is transported between accommodations each day while you walk, so you only carry a daypack on the trail. One bag per person, no more than 20kg. Don't tie bags together or attach loose items like shoes or umbrellas — these will be removed and not transferred. Leave your clearly labelled bag at reception for collection each morning.

When visiting churches, cathedrals, and religious sites, modesty is expected. Covered shoulders and knees are the standard. Comfortable, smart-casual clothing is appropriate for evenings at restaurants. Some accommodations are in fine historic buildings where a slightly smarter outfit for dinner is a nice touch, though nothing formal is required.

A 20–30 litre daypack with a waterproof cover and liner. Key items include a quality waterproof jacket, warm layer, lightweight walking trousers, sturdy boots (not trainers), wide-brimmed sun hat, sunscreen (SPF 15+ minimum), sunglasses, at least 2–3 litres of water, food and snacks for the day, a personal first aid kit, your passport, cash in Euros, and your walk notes and maps. Gaiters are worth considering — they help keep grass seeds and debris out of your boots on the country tracks. Walking poles are optional but useful on steeper descents, particularly in the Chianti hills.

Italy uses the Euro (€). Cards are accepted almost everywhere, but carry cash too — many smaller villages have no ATMs, and you'll want Euros for local cafés, food shops, and tourist taxes. Stock up in larger towns when you can. Keep a note of the tourist tax requirement — this is paid directly to the accommodation on checkout and is typically not included in your package price.

Tipping is not mandatory in Italy, but rounding up the bill or leaving a few Euros at a restaurant is a perfectly normal and appreciated gesture for good service. There's no set expectation — tip at your own discretion.

Yes. Travel insurance is mandatory and must cover walking activities, trip cancellation, loss of luggage, and helicopter rescue. Emergency helicopter evacuation in Italy is a chargeable service — without adequate cover, the costs can be very high.

Flag any allergies or dietary needs at the time of booking and reconfirm with your host on arrival at each property. Tuscan cuisine is ingredient-driven and beautiful, but it can be harder to accommodate complex requirements in smaller rural accommodations. Be specific when you book — there can be confusion around what "vegetarian" means in this context (some places consider fish or white meat acceptable). If you have severe allergies, bring supplementary snacks as backup. A useful phrase: "Sono allergico a..." followed by "noccioline / latticini / glutine" (nuts / dairy / gluten).

Yes. Most towns along the route have cafés, alimentari (food shops), bakeries, and in larger centres like Montalcino and San Gimignano, CO-OP supermarkets. Note that CO-OPs are typically closed on Sundays — plan your lunch supplies accordingly if you're walking on a Sunday. Your daily walk notes include recommendations for where to eat and stock up along the way.

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The Tuscany Experience

Wonder
Stroll from Etruscan Volterra to Montepulciano through UNESCO-protected Val d’Orcia region
Walking with genuine historical weight beneath your boots. Step into San Gimignano’s UNESCO-listed centre beneath its medieval tower skyline
Explore Siena’s glorious Piazza del Campo and Monteriggioni’s ancient ramparts
Wellness
Tuscany invented slow travel before anyone thought to name it. Slow Down. Breathe in. This is Tuscany at its most honest.
The therapeutic power of this landscape is not dramatic or demanding, it works quietly, through the eyes and the nose and the slow accumulation of beautiful moments
Walk through the World's most painted landscape. Moderate walks along strade bianche, vineyards and gently rolling Siena landscapes
Nature
Follow cypress-lined white roads through Brunello vineyards and chestnut groves.
Picnic beneath olive trees near Poggio Alloro and Poggio Casaglia & enjoy the sunset over the Val d’Orcia from Montepulciano’s hilltop edge.
Recharge in family-run boutique B&Bs, classic townhouses and rural hotels. Soak in Bagno Vignoni’s thermal baths.