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Hill Towns of Tuscany Highlights

6 Days & 5 Nights 4.8 Read 18 reviews
  • Hike iconic Tuscany and its hilltop towns of Montepulciano, Pienza, and Montalcino
  • Savor bold Vino Nobile and sweet Vino Santo within the antique cellars of Montepulciano
  • Listen to the Benedictine monks of Sant ‘Antimo Abbey for blissful, harmonic Gregorian chants
  • Roam the golden grasslands of Val d’Orcia, an inspiration to Renaissance poets, writers and artists
  • Discover the fresco masterpieces of Monte Oliveto and healing thermal baths of Bagno Vignoni
Our signature walking trip through southern Tuscany to the best hilltop towns of Montepulciano, Pienza, Montalcino and Buonconvento. Eat, drink and walk your way through Tuscany's captivating landscape, relaxing in exquisite hotels and wellness spas, while we take care of everything else. Set in the hills south of Siena, experience the Vida Dulca (sweet life) of this area, enjoying lovely walks interspersed with lavish lodging, cultural interests and culinary delights. Taste the sharp and salty flavors of Pecorino cheese with a local artisan, savor 100% Sangiovese Brunello's at a wine tasting in Montalcino and enjoy a traditional “Toscana” dinner at the rustic chic restaurant of your tranquil countryside hotel. Unwind in the healing waters of ancient Etruscan hot spring baths and within the pretty streets and brick archways of overnight hamlets. Stroll along Pienza’s Via Dell’Amore (love way) for picturesque views of the Val d’Orcia, fertile grasslands and iconic cypress tree lined paths.
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This unforgettable “highlights” tour in Southern Tuscany is perfect for active walkers looking for a dynamic mix of culture, comfort and cuisine. Pair Brunello wines with Pecorino cheeses, enjoy (and cook) authentic Italian recipes and relax within lovely hotels. Daily walks are graded moderate and average 9 miles (4-6 hours) along farm tracks, dirt paths and minor country roads to explore the classic landscapes of the Val d’Orcia and Crete di Sense south of Siena.

Tour Style:

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


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

Activity Level & Terrain

Grade & Terrain

We have created this “signature” itinerary to showcase the best walks and to create the perfect balance of sightseeing and cultural experiences.

This tour is graded easy to moderate with 4 days of walking and a maximum distance of 11 miles. Daily walks average around 9 miles (6 hours) along rolling terrain as you walk to-and-from hilltop villages.

Most of the route follows farms tracks and dirt trails, while on some days you will be walking along minor country roads with minimal traffic. On the fourth and fifth day of this trip, the walking is a bit more challenging due to the rugged ups and downs of the Tuscan region south of Siena. 

You should be in decent physical shape and comfortable walking every day to fully enjoy the walking on this tour.



While the route is not waymarked (with the exception of some sections), navigating is easy using the Macs Adventure Navigation App.

Your daily walks will be mapped in the app with GPX tracks, including route notes and turn-by-turn directions. All of these resources are available to download for offline use. More information is outlined within your detailed information pack, in addition to 24/7 telephone support from Macs Adventure should you require assistance.



Included in this trip are overnights in hand-selected accommodations. We’ve carefully selected properties to ensure that you enjoy every minute of your stay while in Tuscany.

Single Rooms & Solo Walkers

This trips is based on two people sharing a room. If you’d like separate rooms, a single supplement is required.

If you would like to request a twin room (same room with two separate beds), please notify us at the time of booking so we can request this option.

This trip is also available to solo walkers (a solo supplement is required).


Breakfast is included each morning and consists of a traditional European style breakfast ranging from coffee, tea, yogurt, granola, seasonal fruit, meat, cheese and baked goods. In most cases, a hot dish (eggs and pancakes) will be served a la cart or can be ordered off a menu.

Lunches and dinners are not included in this trip, so you are free to choose from nearby available options. We recommend finding cafés or restaurants located in the towns or along the walking route, or you can purchase snacks and a picnic lunch to bring along with you. Further information can be found within your information pack and route notes.

  • Overnights in boutique hotels and country inns
  • Breakfasts included
  • Private transfers as per the itinerary
  • Luggage transfers
  • Turn-by-turn route notes
  • Detailed information pack
  • Macs Adventure Navigation App
  • 24/7 Telephone support
  • Flights
  • Travel to Chiusi Train Station
  • Private Transfer from Chiusi Train Station to Montepulciano (arrival)
  • Travel from Siena (onward travel)
  • Travel insurance
  • Lunches, dinners, drinks and snacks
  • Personal equipment
  • Additional nights before, during or after the trip
  • Private Transfer from Chiusi Train Station to Montepulciano (arrival)
  • Travel from hotel to Siena Train Station (onward travel)

When To Go


This tour is available to start anytime between March and October. 

As Tuscany is a very popular destination, we suggest you book as soon as your plans are finalized to ensure availability for specific dates.

When to Go?

The springs months of April, May and June offer warm sunshine, fewer crowds and pleasant conditions. The autumn months of September and October are also a favorite time of year, boasting cooler weather and a striking landscape made up of a yellow, gold and red pallet.

July and August are also great months to go but can be very hot for walking. If booked during these months, we therefore advise you to start your walk very early in the morning to avoid the midday heat.

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;

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.

Luggage Transfer

Luggage Transfer

Your bags will be transferred from your accommodation as per your itinerary and moved onto your next overnight accommodation. We ask you to limit your luggage to one bag of up to 50 lbs. 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.



Our pre-departure information pack has  detailed advice and a packing list on what to bring. This includes warm and cold walking gear, hiking boots, rain gear, day pack and other specifics. 

Travel Insurance

Travel Insurance

Travel insurance helps protect your travel investment, your belongings and most importantly you, from unforeseen circumstances that may arise before or during your trip.

How fit do I need to be?
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What happens if I become ill or can’t walk a stage?


Day 1 Arrive Montepulciano Day 2 Walk to Pienza 9.5 miles / 15 km Day 3 Walk to Bagno Vignoni Thermal Baths 9.5 miles / 15 km Day 4 Walk to Sant’ Antimo, transfer to Montalcino 9 miles / 14 km Day 5 Walk through the Crete Senesi to Buonconvento 10.5 miles / 17 km Day 6 Onward Travel from Buonconvento

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