Self-Guided Walking Tours & Biking Tours


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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.


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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 $1,610

Hill Towns of Tuscany Highlights

Hill Towns of Tuscany Highlights is a captivating short break, capturing the best of the southern Tuscan landscape while walking between fascinating medieval and Renaissance towns.

Duration: 6 Days & 5 Nights
Available: March - October
From $1,230

Classic Tuscany Short Break

Spend 4 nights exploring Tuscany on foot, walking between atmospheric ancient hilltop towns of Volterra, San Gimignano, Colle Val D’ Elsa and Siena.

Duration: 5 Days & 4 Nights
Available: May - October
From $920

Classic Tuscany

A week under the Tuscan sun; with 3 days of walking between hill-top towns, with time to relax and explore Volterra, San Gimignano, Colle Val D’Elsa Monteriggioni and Siena.

Duration: 8 Days & 7 Nights
Available: May - October
From $1,300

Treasures of Tuscany & Umbria

Walk from the medieval and Renaissance hill-top towns of Siena and Pienza in Tuscany, on to historic Perugia in Umbria, and ending in iconic Florence. Nestled in the green heart of Italy, you’ll walk through landscapes of rolling hills, past soldier-straight lines of cyprus trees, through vineyards and olives groves.

Duration: 10 days & 9 nights
Available: Mid April - late October
From $1,810

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 $1,885

Tuscany: Chianti in Luxury

Walk Tuscan wine trails through the timeless landscapes of Chianti to Siena, staying in luxury accommodations.

Duration: 7 Days & 6 Nights
Available: April - October
From $3,460

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.

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