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Hill Towns of Tuscany

8 Days & 7 Nights 4.5 Read 47 reviews
  • Southern Tuscany’s Val d’Orcia; Montepulciano, Pienza, Montalcino.
  • Walks between Renaissance and medieval towns, vineyards and olive groves.
  • The thermal baths at Bagno Vignoni.
  • Sant’ Antimo Abbey; serenity and the sound of monastic chants.
  • Great Italian food and wine; Brunello di Montalcino, Nobile di Montepulciano.

Walk between Renaissance and medieval hill-top towns of southern Tuscany, discovering Montepulciano, Pienza, Bagno Vignoni, Montalcino, and finally Siena. Your journey winds through a unique linear, almost geometric landscape of hills, vineyards and olive trees.

Highlights include the spa baths at Bagno Vignoni and former Benedictine monastery at Sant’ Antimo Abbey. You’ll follow rewarding trails through the lesser known wine regions south of Siena. Take your time, slow down and discover the tastes and textures of Tuscany, one of Italy’s most beautiful and historic regions.

What To Expect

If you enjoy a good day’s exercise with plenty of historic interest amidst picture-postcard scenery, all followed by outstanding accommodation, food and wine, then you will absolutely love this walking holiday.

Trip Style:

Self Guided | Go at your own pace on an independent holiday.


Multi Centre Walking | You will spend multiple nights in one or more of the locations on this walking holiday

This trip is suitable for:


Ideal if you have an interest in:

  • Foodie Adventures
  • Wine, Whisky & More...
  • Special Occasions

Grade & Terrain

This trip is graded ‘easy to moderate’ overall, however it should be noted that the terrain is hilly and summer temperatures can be high. Most of the route follows dirt tracks and trails, and you will be following minor roads only occasionally. On days 4 & 5 the walking is graded more towards the ‘moderate’ side as these are more challenging days.


The routes are waymarked in some areas, but not in others. However we provide you with detailed turn-by-turn route notes and maps and you will also have access to the Macs Adventure Smartphone App enabling you to follow the route using your phone's GPS so you will have no problems finding the way.

Accommodation Information

Stay in lovely 3 star hotels and country inns (agriturismo). We carefully select small and friendly accommodation that offers great value, food and welcomes, so you enjoy every minute of your stay. Many of our walkers choose to add extra nights along the walk to sample more of the wonderful walking and attractions available in Tuscany. If you choose to extend your holiday we would recommend spending extra nights in Pienza, Montalcino or Siena.

Accommodation Details

We will always try and accommodate you at the locations detailed below, but because of limited availability we may have to accommodate you at an alternative location of the same or better standard.

Single Rooms

This independent walking holiday is available to solo walkers and a supplement is payable, as some of the costs are not shared. If you require single rooms in your party we will of course try to accommodate your request, subject to availability and payment of a single supplement.


The delicious Tuscan food and wine available locally is undoubtedly a highlight of this holiday. The price of your holiday includes a hearty breakfast each morning. Lunch and dinner are not included so you are free to choose from the available options. Most of your accommodations will more than happy to provide a packed lunch on request and this can be booked on arrival. Alternatively your route includes details of local shops and convenient lunch stops on the way. Dinner is available either at your accommodation or nearby restaurants.

  • Overnights in small hotels and country inns (3-star standard).
  • Breakfasts included.
  • Daily baggage transfers between hotels.
  • Taxi transfers as per itinerary
  • Information Pack, maps, route notes, GPX tracks, access to our smartphone app.
  • Emergency telephone support from our local partner and UK office.
  • Travel insurance (required).
  • Travel to starting point/from finish
  • Lunches, dinners, drinks and snacks.
  • Taxi transfers or public transport should you need to skip a stage.
  • Personal equipment
  • Extra nights before, during or after your walk
  • Private airport transfers.

When To Go

This tour is available from March to November. Although you can walk in July and August if you want it is not recommended as it can get very hot. 

Getting to the Start

We recommend flying to Pisa, Florence or Rome, and then you can catch the train from the city centre railway station to Montepulciano (usually changing in Chiusi or elsewhere). Approx. journey times to Montepulciano; Pisa 2h50-3h20, Florence 1h50-2h15, Rome 1h50-3h15).  Train timetables are available at Trenitalia; www.trenitalia.com  If you wish, from Chiusi you can opt to take a local bus, or taxi the short distance to Montepulciano (25 mins, payable locally).


Getting from the End

From Siena you can take the train back to Pisa (2h00-3h15), Florence (2h15-3h15) or Rome (2h15-3h20). Again, please see Trenitalia’s website for timetable planning.

Baggage Transfer

Your bags will be collected from your accommodation each day and moved onto your overnight accommodation. We ask you to limit your luggage to one bag of up to 20kg per person.

General Information

The distances and ascent/descents are approximations of the recommended routes. Please be prepared by packing all necessary items, for example, proper rain gear (jacket and pants), sun hat, sunscreen. Your information pack has a detailed equipment list which includes standard walking gear such as good walking boots or shoes, warm and waterproof clothes for the cooler months and lightweight clothing for summer, and a day pack.


Your information pack has a detailed equipment list which includes standard walking gear such as good walking boots or shoes, warm and waterproof clothes and a day pack.

Travel Insurance

It is a requirement of booking this tour with Macs Adventure that you have suitable travel insurance which covers you for the activity and emergency evacuation and hospital care.

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Day 1 Arrive Montepulciano Day 2 Walk to Pienza 9.5 miles / 15 km Day 3 Walk to Bagno Vignoni Thermal Baths 10 miles / 16 km Day 4 Walk to Sant’ Antimo, transfer to Montalcino 9 miles / 14 km Day 5 Walk through the Crete Senesi to Buonconvento 11 miles / 17 km Day 6 Loop Walk to Monte Oliveto Maggiore Monastery 7 miles / 11 km Day 7 Transfer to Grancia di Cuna Medieval Farm, walk to Siena 11 miles / 17 km Day 8 Onward travel

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