Stroll
Hilltop Towns of Tuscany - 6 Days
ItalyTuscany

Hilltop Towns of Tuscany - 6 Days

6 Days
Moderate

Overview

Walk across a timeless region of Tuscany to the medieval hilltop towns of Volterra, San Gimignano and Monteriggioni. Follow ancient Etruscan trails and pilgrim routes through vineyards and olive groves ending in the majestic Piazza del Campo in Siena.

The walk begins deep in the heart of Tuscany at Volterra, one of the most ancient Etruscan settlements. Set atop a high plateau, explore its labyrinth of cobbled streets awash with Roman and medieval architecture. Head east across a rolling landscape peppered with sleepy hamlets as the impressive 14 medieval towers of San Gimignano come into view.

Continue on your journey to Siena along the pilgrim route, Via Francigena. As thousands of pilgrims have before you, walk the classic white gravel roads, stopping to explore the perfectly preserved 13th-century walled town of Monteriggioni. The final day of this Tuscan discovery ends in Siena's lively Piazza del Campo, the perfect spot to kick back and relax with an Aperol Spritz.

Highlights

  • Walk across classic Tuscan landscapes, exploring medieval hilltop towns
  • Discover the Etruscan settlement of Volterra
  • Wander the majestic Piazza del Campo, Siena
  • Spend 2 nights in the exquisite medieval town of San Gimignano
  • Explore the 13th century fortified walled town of Monteriggioni
  • Walk along a section of the ancient Via Francigena pilgrim path

Loading overview…

What's Included

Accommodation

3-star Hotel (4 nights), B&B (1 night)

Transfers

  • Private Vehicle Transfers
  • Luggage Transfers

Meals

5 breakfasts, 0 lunches, and 0 dinners

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

4

Days on the trail

13-21 km

Average per walking day

251-486 m

Gain per day

6/10

Trail difficulty

Where You'll Stay

Nights are spent in small family-run boutique guesthouses and three-star hotels, each chosen for their character, location and connection to the region. Your hosts are genuinely knowledgeable about the history and culture of the towns you pass through and are always happy to share recommendations. Occasional substitutions of equivalent quality may be made — these will always be discussed during the booking process.

What You'll Eat

Five breakfasts are included throughout the walk. Lunch and dinner are yours to explore independently each day, with cafes, food stores and restaurants available in the towns along the route. Your hosts will happily provide a list of local dining recommendations each evening. 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.

More About This Trip

The walk starts in Volterra and finishes in Siena. The closest airports are Florence, Pisa and Rome, all with good train connections to Siena, from where we can arrange a private transfer to Volterra, or you can use public transport links.

From Florence Airport, take the airport train into Florence city centre and connect to a direct service to Siena, a total journey of around two hours. From Pisa Airport, take the Pisa Mover shuttle to Pisa Centrale and connect to Siena via Empoli, taking around one and a half to two hours. From Rome's Fiumicino Airport, trains connect through to Siena in around two and a half hours with one change in Rome. From Ciampino Airport, take the airport bus to Ciampino station and connect to Siena via Rome, also around two and a half hours.

At the end of the walk, Siena has excellent train connections back to all three airports for onward travel.

This walk is available from late April to the end of June and from mid-August through to October. Spring is a wonderful time to walk, with warm sunny days, flowering vineyards and sunflowers coming into bloom through June. Mid-August into September marks the beginning of the grape harvest, bringing a festive energy to the villages and the chance of stumbling across a local harvest celebration. October offers warm days with cooler evenings and a quieter, more contemplative atmosphere. Tuscany can experience afternoon thunderstorms during the warmer months, so packing layers and a waterproof jacket is always wise, regardless of the season.

This walk is graded moderate, with daily distances averaging around 15km and up to 500m of ascent and descent. The trails are well-defined and varied, covering forest tracks, gravel paths, rolling farmland and vineyards, with short steep sections and some rough surfaces along the way. As is common in Italy, separate footpaths are not always available, so some walking on roads is inevitable — please be mindful of other road users at all times. A training regime of two to three times per week is recommended. Daily walk notes, maps and GPX tracks are provided for each day.

A detailed information pack and itinerary will be sent to you around six weeks before departure, covering everything you need to know for a seamless experience. In the meantime, our team is always on hand to answer any questions.

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. See the FAQ section for full details.

Dates & Pricing

Choose Your Start Date

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

August 2026

Mon
Tue
Wed
Thu
Fri
Sat
Sun
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
Available
Limited
Unavailable

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

Tuscany reviews

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.

Want to Know More?

Call Us

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.

From

£740/person