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Hill Towns of Tuscany Highlights

6 Days & 5 Nights 4.8 Read 16 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.
This highlights tour showcases Renaissance and medieval towns nestled amongst the hills of south Tuscany. Walk from Montepulciano to Pienza, visit Sant’ Antimo Abbey and the baths at Bagno Vignoni. Then it’s on to Montalcino before finishing in the ‘Crete Senesi’ area around Buonconvento. Slowly make your way on foot through these tranquil wine regions and escape the pace of 21st century life whilst discovering the highlights of southern Tuscany’s architecturally and historically fascinating towns and monasteries.

What To Expect

Taking in the highlights of south Tuscany over 5 nights, and is perfect for active walkers looking for an appreciation of Tuscany’s culture, cuisine and history. Combine these key ingredients with Tuscany’s idyllic rolling hills and charming accommodation, and you have a superb walking tour!

Trip Style:

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

Activity:

Inn to Inn Walking | A classic point to point walking trip, staying in a different location each night

This trip is suitable for:

Multi-Generational, Groups > 10

Ideal if you have an interest in:

  • Historical Journeys
  • 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.

Navigation

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.

Meals

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.

Included
  • 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.
Excluded
  • 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
Extras
  • 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

By Air: 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

At the end of your trip, we transfer you to Buonconvento train station, where you can catch the train to Siena. 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.

Equipment

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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Itinerary

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 Onward Travel

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