Hill Towns of Tuscany Highlights

From $1,425.00
6 Days & 5 Nights
Read 21 reviews

Hill Towns of Tuscany Highlights

  • Explore the famed hill towns of Southern Tuscany on foot
  • Scenic walks between Renaissance and medieval towns, vineyards, and olive groves
  • Relax and recharge in the thermal baths at Bagno Vignoni
  • Time to reflect and listen to the sound of monastic chants in Sant’ Antimo Abbey
  • Fantastic cheese, pasta, and wine including Brunello di Montalcino and Nobile di Montepulciano
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.


Day 1 Arrive in Montepulciano, transfer to the town centre Day 2 Walk from Montepulciano to Pienza 9 miles / 15 km Day 3 Walk from Pienza to Bagno Vignoni Thermal Baths 9 miles / 14 km Day 4 Walk from Bagno Vignoni to Sant’ Antimo Abbey; transfer to Montalcino 8 miles / 13 km Day 5 Walk from Montalcino through the Crete Senesi to near Buonconvento 10 miles / 16 km Day 6 Transfer to Buonconvento Train Station; onward travel

Other Information

Is it for me? Accommodation & Meals Navigation What's Included When to go Travel & Transfers Info & FAQ

Why Macs

Reasons to believe in Macs Adventure:
The biggest choice

The biggest choice

Self-guided hiking & biking is all we do - we have over 500 tried & tested trips.
Our Heritage

Around since 2003

We’re still founder led & the world’s number one self-guided operator with mountains of experience.

18,000+ customer reviews

Plus, with a Feefo Platinum Service Award & a British Travel Award, you know you're in good hands.
Positive Impact

Positive impact

We use independent suppliers to support communities along our routes, as well as work with organizations to help maintain & restore paths.
The Macs Way

At Macs, we don’t do tour buses, groups, or guides. Instead, we give you the freedom and confidence to have your own self-guided hiking or biking adventure

It's active travel, led by you.

Travel on your terms

You choose your departure date and who you travel with, we do the rest.

The people behind your journey

We sort accommodation and luggage transfers and provide your route in an easy-to-use app.

Here when you need us

We give you everything you need to travel independently but we're here 24/7 if you need us.

Achieve something

Getting from A to B under your own steam is intensely rewarding. With Macs, you'll see the world, and yourself, differently.

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