Tuscany Experience
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5 days 9 days
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1174
Chianti Classico Experience
1174
Bookatrekking.com Trips
Italy
Explore Tuscany’s rolling hills with gentle walks, world-class wines, and welcoming stays. Stroll through vineyards and medieval villages, savor authentic Italian flavors, and enjoy the beauty of Chianti at your own pace.
Duration: 7 days
Trails: T2 trails
Distance: 10 - 15 km / 6 - 9 mi per day
Ascent per day: 250 - 500 m / 820 - 1640 ft ascent per day
1192
Via degli Dei Experience
1192
Bookatrekking.com Trips
Italy
Embark on a journey through history with the Via degli Dei Experience, where ancient trade routes intertwine with breathtaking landscapes. Wander through dense forests, gentle mountain slopes, and charming Italian villages. Savor the flavors of Emilia-Romagna and Tuscany with every step, and let welcoming stays turn your adventure into an unforgettable Italian escape.
Duration: 8 days
Trails: T3 trails
Distance: 15 - 20 km / 9 - 12 mi per day
Ascent per day: 250 - 500 m / 820 - 1640 ft ascent per day
1174
Val d'Orcia Panorama Experience
1174
Bookatrekking.com Trips
Italy
Step into the heart of Val d'Orcia with panoramic hikes, timeless Tuscan beauty, and cozy accommodations. Wander through golden hills, ancient villages, and indulge in Italy's iconic flavors at every turn.
Duration: 7 days
Trails: T2 trails
Distance: 10 - 15 km / 6 - 9 mi per day
Ascent per day: 250 - 500 m / 820 - 1640 ft ascent per day
1433
Via Francigena Experience
1433
Bookatrekking.com Trips
Italy
Step into history on the Via Francigena Experience, where ancient pilgrim paths meet breathtaking landscapes. Wander through rolling hills, medieval villages, and sun-drenched vineyards. Relish the flavors of Tuscany with every step, and let welcoming stays turn your journey into a timeless Italian escape.
Duration: 9 days
Trails: T2 trails
Distance: 10 - 15 km / 6 - 9 mi per day
Ascent per day: 250 - 500 m / 820 - 1640 ft ascent per day
837
Best of Chianti
837
Bookatrekking.com Trips
Italy
A 5-day village-to-village trek through Tuscany’s Chianti region, where gentle trails, fine wines, and charming towns come together for the perfect slow travel experience.
Duration: 5 days
Trails: T1 trails
Distance: 15 - 20 km / 9 - 12 mi per day
Ascent per day: 500 - 1000 m / 1640 - 3281 ft ascent per day
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Natascha Langelaan
837
Via Francigena to San Gimignano
837
Bookatrekking.com Trips
Italy
Walk the Via Francigena from San Casciano to San Gimignano with your luggage transferred each day. Enjoy 4 to 5 hours of easy walking through olive groves, quiet villages, and scenic trails. Stay in charming local accommodations and end your journey at the medieval towers of San Gimignano.
Duration: 5 days
Trails: T1 trails
Distance: 15 - 20 km / 9 - 12 mi per day
Ascent per day: 250 - 500 m / 820 - 1640 ft ascent per day
837
Intense Val d'Orcia Trek
837
Bookatrekking.com Trips
Italy
Hike from Pienza to Montalcino in just three days and experience the best of the Val d'Orcia. Sleep in charming villages, walk through golden hills, and unwind in thermal springs. Perfect for an active long weekend in Tuscany.
Duration: 5 days
Trails: T2 trails
Distance: 15 - 20 km / 9 - 12 mi per day
Ascent per day: 500 - 1000 m / 1640 - 3281 ft ascent per day
837
Half Via degli Dei
837
Bookatrekking.com Trips
Italy
Hike the iconic first stretch of the Via degli Dei from Bologna into the heart of Tuscany. This 5-day trip includes 3 full trekking days through rugged Apennine trails with cozy countryside stays and accommodation in Bologna before and after. A proper Italian trekking adventure — no fluff, all trail.
Duration: 5 days
Trails: T3 trails
Distance: More than 20 km / 12 mi per day
Ascent per day: More than 1000 m / 3281 ft ascent per day
Find Tuscany Experience Hiking & Trekking Trips
Explore Tuscany's rolling hills, charming medieval towns, and world-class vineyards. From Val d'Orcia to Chianti , every step reveals stunning landscapes and rich traditions. Sip fine wines, savor local delicacies, and enjoy the simple beauty of la dolce vita.
Tuscany is waiting—are you ready?
So lace up your boots, grab a glass of vino, and let Tuscany's landscapes and flavors work their magic. A trip to Tuscany isn't just a journey—it's a celebration of la dolce vita.
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