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Tuscany: Hilltop Towns

8 Days & 7 Nights 4.5 Read 47 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
Walk the romantic and off-the-beaten paths of southern Tuscany, discovering the hilltop towns of Montepulciano, Pienza, Bagno Vignoni, Montalcino and the city of Siena, a UNESCO World Heritage Site. Wander through classic Tuscan landscapes of rolling hills, vineyards and olive groves to Renaissance towns and hilltop hamlets. Explore the fresco masterpieces depicting the life of Saint Benedict at Monte Oliveto and hear the Gregorian chants of white-robed monks in Sant’ Antimo Abbey. Walk the lovely landscapes of southern Tuscany and the lesser known wine regions south of Siena. Unwind in the healing waters of ancient Etruscan hot spring baths or with a glass of wine at restaurants serving only the most authentic, seasonal and gourmet Italian cuisine. Each evening, enjoy authentic Italian hospitality at its finest, staying in hotels within the pretty streets of Medieval towns or at agriturismos deep within the Tuscan countryside.
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This tour is perfect for active walkers, art lovers and history buffs that desire 7 nights to fully explore idyllic Tuscany and the Val d’Orcia. This trip is graded easy to moderate with six days of walking ranging from 7-11 miles (6 hours) along farm tracks, dirt paths and minor country roads to the hilltop towns of the “Crete di Senese.” Enjoy full days of exercise with plenty of food, wine and picture-postcard scenery, and evenings within charming boutique hotels and country inns.

Tour Style:

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


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

This trip is suitable for:


Ideal if you have an interest in:

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

Activity Level & Terrain

Grade & Terrain

This tour is graded easy to moderate with six days of walking and a maximum distance of 11 miles. Daily walks average around 7-11 miles (9 on average, 4-6 hours) along rolling terrain as you walk to-and-from hilltop towns.

Most of the route follows farm 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

Getting to Chiusi-Chianciano 

By Air & Train:

Florence, Rome and Pisa all have airports with flights from international and national destinations. 

We recommend flying into Florence and taking a taxi from the airport to the Florence Train Station. On an average weekday, there are 23 trains per day traveling from Florence to Chiusi-Chianciano Terme (approx. 2 hours, 10 euros).

If flying into Rome, take the Leonardo Express train from the airport to Rome Termini (Main Train Station). Trains to Chiusi-Chianciano Terme from Rome depart several times per day (approx. 1.5 hours, 10 euros). 

If flying into Pisa, take the tram from the airport to the Pisa Centrale Train Station. On an average weekday, there are 28 trains per day traveling from Pisa to Chiusi-Chianciano Terme (approx. 3.5 hours, 18 euros).

Prices, ticketing and more information can be found within your pre-departure information pack. For additional information, please check the Trenitalia website for updated timetables.

Getting to Montepulciano

Upon arrival to Chisui-Chianciano Terme Train Station, take a local bus or call a taxi (typically lined up outside the train station) for transport to Montepulciano (payable locally).

A private transfer from the Chiusi-Chianciano Terme Train Station to Montepulciano can be included in this trip (approx. 30 minutes). Please let us know at the time of booking if you desire to add this option (additional costs apply).

Getting from the End

Getting from Siena

From Siena, you can take the train to Florence, Pisa, Rome or any desired onward travel destination. Please see the Trenitalia 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.

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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) 9.5 miles / 15 km Day 4 Walk to Sant’ Antimo, transfer to Montalcino 9 miles / 14 km Day 5: Walk the “Crete Senesi” to Buonconvento 10.5 miles / 17 km Day 6: Walk Monte Oliveto Maggiore to Buonconvento 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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