Hiking & Trekking Tours & Trips in Tuscany
Have you ever wanted to walk where medieval pilgrims once tread? The Via Francigena winds from Canterbury all the way to Rome, cutting right through Tuscany's olive groves and UNESCO-listed Val d'Orcia. You'll climb Monte Prado in the Alpi Apuane, traverse Apennine ridges, and basically experience Italy the way it was meant to be seen – on foot, slowly, with plenty of wine breaks.
10 best hiking & trekking Tuscany tours
Compiled by
MelissaTuscany travel expert at TourRadar
- Tuscany Walks & Chianti Wines
- Tuscan Coast
- Walking Northern Tuscany
- Picturesque Tuscany
- Best of Chianti: Walk & Wine
- A Taste of Tuscany Self-Guided Walking
- Tuscany: hilltop towns of Val d’Orcia & Siena (Self-guided Walking Tour)
- Malerische Toskana mit Charme
- Tuscany Walking & Hiking Tour
- Walking Trails of Hidden Tuscany
Tuscany Walks & Chianti Wines
26 Reviews by TourRadar travelers“The lodging was great and the guide, Liz was very competent both driving and guiding.”
mireilleamyotte, traveled in October
Scenic trails await near San Gimignano at Hotel Le Renaie. The historic Via Francigena and Radda in Chianti's woodlands reveal hidden valleys, while moderate hikes offer spectacular vineyard views and cultural visits.
Duration 8 days Destinations Pancole, Gambassi Terme, San Gimignano, Fonterutoli, Castellina in Chianti, Siena, Certaldo, Florence Age Range Ages 18+ Physical Rating Moderate Distance 104 mi Operator Exodus Adventure Travels From
- US$3,375
Duration 8 days Destinations Pisa, San Giuliano Terme, Livorno, Castiglioncello, Cecina, Bolgheri, Castagneto Carducci, Piombino, Elba, Portoferraio Age Range All Ages Welcome Operated in English, German Physical Rating Moderate Distance 91 mi Operator Eurohike From
- US$1,206
Walking Northern Tuscany
151 Reviews by TourRadar travelers“Walks were really good, and Sara an excellent guide.”
Ian, traveled in September
The pristine landscapes of Garfagnana set the stage for mountain hiking. The route leads from Braccicorti to Monte Sumbra (5,791ft), through Orecchiella National Park, and to Castiglione di Garfagnana, complete with home-cooked meals and optional excursions.
Duration 8 days Destinations Pontecosi, Corfino, Pania della Croce, Careggine, Villa Collemandina, Castiglione di Garfagnana, Vagli Sotto, Vagli Sopra Age Range Ages 16+ Physical Rating Moderate Distance 40 mi Operator Exodus Adventure Travels From $2,803
12% Off- US$2,475You save $328
The finest trails of Tuscany unfold from Florence's Renaissance center to Cecina's coast. Daily routes of 11-16km wind through Chianti vineyards, Monte Nero nature reserve, and ancient salt routes, featuring moderate climbs of 350-500m.
Duration 8 days Destinations Florence, Greve in Chianti, Castellina in Chianti, Siena, San Gimignano, Volterra, Cecina Age Range All Ages Welcome Operated in English, German Physical Rating Moderate Distance 79 mi Operator Eurohike From
12% Off- US$1,159
Duration 5 days Destinations Greve in Chianti Age Range Ages 18+ Physical Rating Easy Operator Bookatrekking From
12% Off- US$806
Tuscany's diverse landscapes spread out from Agriturismo La Pietriccia base. Daily walks of 5-15km lead through Chianciano Vecchia's trails, Lake Chiusi's shoreline, and the UNESCO Val d'Orcia, featuring Montepulciano's vineyards, Pienza's medieval paths, and Bagno Vignoni's Roman baths.
Duration 8 days Destinations Chianciano Terme, Montepulciano, Pienza, Val d'Orcia Age Range Ages 8+ Physical Rating Moderate Distance 28 mi Operator Exodus Adventure Travels From
12% Off- US$2,105
Tuscany: hilltop towns of Val d’Orcia & Siena (Self-guided Walking Tour)
2 Reviews by TourRadar travelers“The Tuscan towns are amazing. We got a hire car right after the tour, and explored other towns and villages.”
Pete, traveled in June
Val d'Orcia's finest paths lead from Montepulciano's San Biagio church to Siena's medieval streets. Daily routes of 10-15km showcase UNESCO-listed Pienza, Sant'Antimo Abbey, and Monte Oliveto Maggiore Monastery, with strategic transfers included.
No departure dates availableDuration 8 days Destinations Montepulciano, Pienza, Bagno Vignoni, Montalcino, Buonconvento, Siena Age Range Ages 10+ Physical Rating Moderate Distance 36 mi Operator Traventuria 
This 8-day trek takes you along the ancient Via Romea pilgrimage route through Siena's UNESCO-listed Historic Centre, then winds through golden Chianti vineyards from Greve in Chianti to Castellina in Chianti. Walk the historic Via del Sale salt trade route through Monte Nero nature reserve to Volterra's alabaster city.
Duration 8 days Destinations Florence, Greve in Chianti, Castellina in Chianti, Siena, San Gimignano, Volterra, Marina di Castagneto Carducci Age Range All Ages Welcome Operated in English, German Physical Rating Moderate Distance 82 mi Operator Eurohike From
12% Off- US$1,623
Tuscany Walking & Hiking Tour
1 Review by TourRadar travelers“The views were incredible along the way and even though there was a lot of walking, the pace was comfortable.”
Ken, traveled in September
Ancient trails stretch from Cortona's historic walls to Val d'Orcia's rolling hills. The 12km route passes through olive groves to Saint Francis's hermitage, along Roman roads between vineyards, and hidden paths linking Montepulciano to Monticchiello, with moderate ascents over 3-4 hours.
No departure dates availableDuration 8 days Destinations Cortona, Monticchiello, Montepulciano, Siena, Pienza, San Quirico D'orcia, Bagno Vignoni, Buonconvento, Asciano, SI Age Range Ages 25+ Physical Rating Moderate Distance 120 mi Operator Caspin Journeys
What people love about Hiking & Trekking Tours in Tuscany
Everything from our amazing tour leader Jordan to Hotel Le Renaie was perfect. Sad to leave the amazing scenery and people of Toscana. Would love to return one day.
Tuscany Walks & Chianti Wines
- Walking Northern Tuscany
Walks were really good, and Sara an excellent guide. Weather was not all you could hope for, but that is out of anybody's control
- Tuscany: hilltop towns of Val d’Orcia & Siena (Self-guided Walking Tour)
We enjoyed our trip & most all of the hotels & breakfasts. The walk was a lot harder than anticipated; what was described as an easy walk turned out to be a lot of steep uphill terrain. We thought the price was great & we always received our luggage on time. Having to confirm our transfers was a problem as no one spoke English & they didn’t understand my Italian. All in all we had a great time & found the navigation APP helpful. We saw some beautiful landscapes & scenery but were so tired by the time we got to town we didn’t really get to enjoy the towns as we would have liked.
What our customers ask about Hiking & Trekking Tours & Trips in Tuscany
What are the best hiking trails in Tuscany for different skill levels?
Tuscany's trail network accommodates walkers of every ability. Moderate routes through the Garfagnana Valley take 4-5 hours and cover 8-12km daily across forests and wine country with paths leading to spots like Pania di Corfino at 1609m. More advanced hikers head to the Apuane Alps where trails stretch 15km and climb 750m in elevation over 6 hours. A TourRadar traveler noted: "The walks were really good with excellent leadership and varied terrain so lots of interesting walking through beautiful valleys and hilltops."
What is the best time of year for hiking in Tuscany?
Peak hiking conditions in Tuscany run from April to October. The sweet spots are May-June and September-October when temperatures stay mild and tourist numbers drop. The Garfagnana Valley runs cooler than the coast with spring bringing carpets of flowers while autumn paints the beech forests in warm colors. Summer gets hot especially in the Val d'Orcia. A TourRadar traveler notes: "Early September is a great time to go as it's not too hot to walk yet still lovely and warm but don't leave it any later than mid-September as the thunder clouds start to roll into the hilly regions."
How physically demanding are Tuscan hiking tours?
Tours range from gentle walks to challenging treks. Standard moderate routes take 4-5 hours covering 8-12km daily with 300-400m elevation gains through areas like Val d'Orcia. The Apennines offer more demanding options with 6-hour hikes stretching 15km and climbing 750m. A TourRadar traveler shares: "Although I enjoy walking and often do around 10 miles at weekends I found the climbing really hard going but enjoyable and the group were great - no stragglers were left behind."
What kind of meals are provided on Tuscan hiking tours?
Tours serve genuine Tuscan food with breakfast and dinner at lodgings plus packed trail lunches. Places like Agriturismo Braccicorti prepare traditional dishes from scratch including fresh pasta local cheeses and regional wines. A TourRadar traveler shared: "Mama's cooking was superb the meals at the Fattoria were delicious and varied and the picnic lunches were excellent."
Are the hiking trails well-marked in Tuscany?
Trail markings change by location. The Via Francigena and national park paths have clear signs and markers. Mountain routes in the Apennines and Apuane Alps need more navigation know-how. Tour guides know these paths well and lead the way. As one TourRadar traveler mentioned: "Sara was fantastic! She took us on trails that tourists don't normally find with beautiful views and very fresh air."
What wildlife might I encounter while hiking in Tuscany?
The varied landscapes of Tuscany especially in the Apennines and Garfagnana support diverse wildlife. Hikers often come across wild boar deer mountain hares and many bird species from buzzards to the occasional golden eagle. A TourRadar traveler noted: "Walking through the Orecchiella National Park we saw signs of wolves deer and mountain hares and the beech forests were full of bird life."