Background Image

Montepulciano to Siena Walking Holidays

Unearth the tranquil allure of Italy's heartland from Montepulciano to Siena, a sensory journey through time-honoured towns and idyllic landscapes.
Starting point
Montepulciano
Finish point
Siena
Duration
9 days / 8 nights
Season
Mar - Nov
Price
From: 1,989€/person
Difficulty
Moderate
Suitable for most active people with with good stamina and basic walking experience
Inquiry

Stroll through the vineyards and olive groves of Tuscany

Explore the mediaeval charm of hilltop towns like Montepulciano and Siena

Savour the flavours of local cuisine and world-renowned wines

Experience the tranquillity of the peaceful village of Montichiello

Marvel at the stunning views of the iconic Tuscan scenery from the hilltop town of Pienza

Visit the isolated Sant’ Antimo Abbey, a gem of Romanesque architecture

Walking on Tuscan path
Discover Italy's heartland on foot through Tuscany
Sant Antimo Montalcino church and olive tree. Orcia, Tuscany, It
Marvel at Sant' Antimo's Romanesque architecture
Beautiful alley in Tuscany, Old town Montepulciano, Italy
Delve into Montepulciano's mediaeval charm
relaxed adventure woman hiker hiking in Tuscany
Seek tranquil adventure in Tuscany's scenic trails
Crete senesi
Immerse in the unique landscapes of Crete Senesi
Aerial view over city of Siena
Behold the architectural marvel of Siena
Casale Marittimo village, vineyards and landscape in Maremma. Tuscany, Italy.
Wander through Tuscany's sun-kissed vineyards
Scenic view of Montichiello, Siena, Italy
Experience the tranquillity of hilltop Montichiello

Included in price

Tour design and organisation

24/7 service and support during your holidays

GPS navigation with an easy-to-use app

7x accommodation with breakfast in 3/4* hotels

Luggage transfer

Optional Extras

Transfer to and from the airport
Single supplement
From:
1,989€
/person
Inquiry

Step into a world where time slows down, where the sweet life, or ‘la dolce vita,’ isn’t just a phrase but a way of being. It’s time for a journey that takes you to the heart of Italy, not through the hustle and bustle of its cities but through the serene beauty of the Tuscan countryside. Here, the charm of mediaeval hilltop towns competes with the allure of sunflower fields, olive groves, and rolling vineyards.

Your adventure will take you through some of the most picturesque towns in Tuscany, from the wine-lovers paradise of Montepulciano to the architectural marvel of Siena. Along the way, you’ll discover the Renaissance splendour of Pienza, the tranquil beauty of Castelnuovo dell’Abate, and the mediaeval charm of Lucignano, among others.

Each town is a gem waiting to be explored, set against the backdrop of Tuscany’s iconic rolling hills and cypress-lined roads.

Our walking holidays are designed with leisure in mind. The hikes are gentle, the pace is relaxed, and there’s plenty of time to explore on your own. You’ll traverse some of the most scenic parts of the Via Francigena, an ancient pilgrimage route, and focus on the most picturesque cities between Montepulciano and Siena.

At Tuscany Walking Holidays, we take care of all the details so you can focus on enjoying your holiday. We oversee the accommodation availability and secure all the bookings, provide a detailed written handout with a day-by-day itinerary, and offer GPS navigation with a user-friendly app.

So, are you ready to swap your office chair for a seat at a Tuscan trattoria, your daily commute for a stroll through a vineyard, and your alarm clock for the morning sun streaming through your window? Come and lose yourself in the Tuscan countryside with us.

Map

Start planning today!

The sooner the better - guaranteed availability and best prices if you don't wait for too long.
Inquire now

Things to know

Book now for guaranteed availability!

Start planning your trip as soon as possible. Flexible booking and Covid Refund Guarantee.
Inquire now

Self-guided

Those who like a good adventure and limitless flexibility should go on a self-guided tour. We prepare the itinerary and book your accommodations while you enjoy the journey without our guide, being fully in charge of all the daily decisions. While you’ll have the full support of our team in case of any emergencies or concerns, a certain level of self-reliance is required.

Private Guided

Experience the great outdoors on a private guided tour tailored just for you. The tour is for those who want a hastle-free adventure and enjoy the flexibility of a small private group and not stress about the details of everyday planning. The guide will be fully at your disposal to make this experience as personalized as possible, maximizing the enjoyment during and after the tour.

Join a Group

For solo hikers or hikers who wish to meet other like-minded souls, don’t want to stress about tour-planning and other annoying details. We’re going to find you a group of like-minded outdoor enthusiasts and take care of all the other details. The tour will be led by our guide, who’ll make sure everything runs smoothly, ensuring maximum hiking enjoyment.

HASSLE-FREE

We handle itineraries, accommodations, and anything else you prefer not to deal with, so you can enjoy a carefree hike.

TRUSTED BY MANY

We are a financially protected company, fully bonded and insured, keeping your money safe and allowing you to travel with confidence.

TRIED & TESTED ADVENTURES

Only the best walking tours in Tuscany, cherry-picked by our team with an in-depth knowledge of the region.

UNBEATABLE SUPPORT

Our 24/7 customer support is where we show our passion, bringing you a better experience by making your well-being our number one priority.

Similar Tuscany Walking Tours

female hiker walking across tuscany hills
A man sipping a glass of Chianti wine with breathtaking views of Tuscany - Italian region famous for its picturesque landscapes and excellent wines -  ai generative
Chianti hills with vineyards and cypress. Tuscan Landscape between Siena and Florence. Italy
Culinary delights in siena
Woman is walking in a tuscan countryside
Sunset view of Florence and Duomo. Italy
Siena city skyline, countryside and rolling hills. Tuscany, Italy
Uffizi Gallery. Piazza degli Uffizi square in the early Sunny autumn morning. Florence, Tuscany, Italy
8 days / 7 nights
Leisurely to Moderate
Embark on a journey through the Chianti region, a land renowned for its artistic heritage, architectural marvels, delectable wines, and unique landscapes.
From: 945€/person
More →
San Miniato bell tower of the cathedral. Pisa, Tuscany Italy Europe.
Pellegrini in cammino lungo la Via Francigena
Monteroni d'Arbia, route of the via francigena. Winding road. Siena, Tuscany. Italy
Landscape along via Francigena with Mud road, fields, trees and vineyard.  Sign showing the direction of Monteroni d'Arbia, route of the via francigena. Siena province, Tuscany. Italy, Europe.
Beautiful view of Dome and campanile of Siena Cathedral, Duomo di Siena, and Old Town of medieval city of Siena at gorgeous sunset, Tuscany, Italy
Pilgrims walking on the path to San Gimignano trough woods and yellow bushes. Solo Backpacker Trekking on the Via Francigena from Lucca to Siena. Walking between nature, history, churches,
Abbadia Isola, Monteriggioni - Toscana
San Gimignano - Toskana
9 days / 8 nights
Moderate to Challenging
Experience the timeless beauty of Tuscany on the historic Via Francigena, a journey through picturesque landscapes, charming hamlets, and UNESCO-listed towns.
From: 1,045€/person
More →
Siena city skyline, countryside and rolling hills. Tuscany, Italy
Cortona, Calcinaio Church
Medieval Street
Trasimeno lake panoramic view,Castiglione del lago fortress, Umbria, Italy
Scenic Tuscany landscape at sunrise, Val d'Orcia, Italy
Oak barrels in an old wine cellar.
Perugia Via dell Acquedotto
Siena
10 days / 9 nights
Leisurely
Discover Italy's heartland on foot, strolling through vineyards, exploring mediaeval towns, and savouring local delicacies across Tuscany and Umbria.
From: 2,089€/person
More →
One Man hiker hiking alone climbing down a steep mountain path in winter. Taken from distance. Matte high contrast effect
View of the Apuan Alps from the Pisa Tower - Italy
Alpi Apuane view from Monte Prana - Pania secca and Pania di Corfino
Blick auf die Alte Brücke und die Altstadt von Castelnuovo di Garfagnana in der Toskana in Italien
Vagli di Sotto village on Lago di Vagli, Vagli lake, Tuscany, It
smiling woman in floral dress exploring attractions
Idyllic landscape with the village of Poggio and the Apuan Alps in the background. Province of Lucca, Tuscany, central Italy.
Alpi Apuane, trekking sul M. Altissimo 2
8 days / 7 nights
Leisurely to Moderate
Experience the embrace of luxury in Tuscany's hidden gem, the valley of Garfagnana, with our meticulously curated self-guided walking holidays.
From: 2,239€/person
More →
Experience the enchanting mediaeval towns, luscious cuisine, and rolling vineyard landscapes with Tuscany Walking Holidays, your gateway to Italian adventures.
Portfolio company of World Discovery.