Self-Guided Walking Tours & Biking Tours


Trip Finder

Walking Tours in Tuscany

Treat yourself to a journey under the Tuscan Sun on one of our Tuscany walking tours, offering some of the best walking in Italy. Experience the rich pastoral landscapes, renaissance towns clinging to hillsides and – of course – the wine that Tuscany, and its Chianti region, is known for.

Discover the tastes and textures of Tuscany, enjoying the almost geometric landscape of hills, 14th century castles, vineyards and olive trees. Days spent walking through the breathtaking, pastoral Tuscan landscape between quaint towns and past monasteries is a magical experience.

While walking in Tuscany, sample the delicious food and wine for which Tuscany is renowned. Visit a few of Tuscany’s historic cities, viewing Michelangelo’s David and the medieval bridge of Ponte Vecchio over the Arno River, on our Florence to Siena tour or experience the cobbled streets, old walls, perched dwellings and exquisite hotels of Tuscany's classic hill towns on our Signature Hilltop Towns tour. Whatever catches your fancy, bask in the picture perfect Tuscany of your dreams.


5 products, viewing 1 - 5
Loading …

Trip Finder Search Results:  Trip   New Trip 

Tuscany: Chianti - Florence to Siena

A classic and full discovery of Tuscany's Chianti wine region from Florence to Siena. Discover Florence, the heart of the Italian Renaissance, and walk the beloved and poetic landscapes of Chianti on foot from Radda in Chianti to Siena, for an unforgettable getaway under the Tuscan sun.

Duration: 9 Days & 8 Nights
Available: April - October
From $1,795

Italy: Tuscany & Umbria

Enjoy the best of Tuscany and the treasures of Umbria on foot, walking from the iconic hilltop towns of Southern Tuscany, into the untouched landscapes of Umbria and to the final highlight of the Renaissance city of Florence.

Duration: 10 days & 9 nights
Available: Mid April - late October
From $2,400

Tuscany: Hilltop Towns

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.

Duration: 8 Days & 7 Nights
Available: March - October
From $1,675

Tuscany: Signature Hilltop Towns

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.

Duration: 6 Days & 5 Nights
Available: March - October
From $2,495

Tuscany: Signature Chianti

Walk through the best and timeless landscapes from Radda and Gaiole in Chianti, to Siena in-style. Pamper your palate with a wine tasting, cooking class and Michelin star restaurant on this signature tour, featuring elegant overnight stays in hilltop hamlets and villas deep within the Chianti countryside.

Duration: 7 Days & 6 Nights
Available: April - October
From $3,295

Book self-guided walking tours and biking tours with Macs Adventure. Explore Europe, the UK and the rest of the world on our walking tours and biking tours, and find out why thousands of people trust us to arrange their perfect self-guided adventure.

Get In Touch

lf you require more information before booking, please contact us on

+44 (0)141 530 5464

+1 -844-858-0740


© 2019

Macs Adventure - US Office: 3200 Carbon Place Suite 102, Boulder, CO 80301


USA & Canada UK & Rest of World