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
- Tuscany Walking & Hiking Tour
- Walking in Tuscany
- Picturesque Tuscany
- A Taste of Tuscany Self-Guided Walking
- Via Francigena - From Chiusi to Città di Castello 6 Days
- Hills of Tuscany - Val d Orcia - Montepulciano to Siena 8 Days
- Picturesque Tuscany - with Charm 8 Days
- Walking in Tuscany
- Tuscany - Discover the Chianti region 8 Days
Tuscany Walks & Chianti Wines
26 Reviews by TourRadar travelers“A fantastic experience, venue and mix of activities. Most importantly our guide Roberta went out of her way to make everyone's experience excellent.”
Potter, traveled in September
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, San Gimignano, Pisa, Florence, Gambassi Terme, Rome, Radda in Chianti, Siena, Certaldo, TuscanySee all destinations Age Range Ages 18+ Physical Rating Moderate Distance 656 mi Operator Exodus Adventure Travels From $3,598
20% Off- US$2,880You save $718
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.
Duration 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 From
20% Off- US$4,247
Walking in Tuscany
151 Reviews by TourRadar travelers“Gorgeous countryside, fabulous accommodation, great food (and wine), and lovely people.”
Morgan, traveled in October
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 $2,998
20% Off- US$2,400You save $598
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
20% Off- US$1,162
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
20% Off- US$2,105
Duration 6 days Destinations Chiusi, Chiusi della Verna, Anghiari, Citerna Age Range Ages 16+ Operated in Only: German Physical Rating Moderate Distance 63 mi Operator ASI Reisen From
20% Off- US$671
This 8-day trek through Tuscany's Val d'Orcia follows trails from Montepulciano to Siena, passing vineyards and cypress-lined hills along the way. You'll visit the Romanesque Monte Oliveto Maggiore Monastery near Buonconvento, hike from Castelnuovo dell'Abate to the wine town of Montalcino, and walk to Renaissance Pienza with its pecorino cheese shops. Daily routes are easy to moderate, and you'll stay in comfortable 3- to 4-star accommodations with 7 breakfasts included. The trip suits ages 16+ looking for Tuscan landscapes and walking at a relaxed pace.
Duration 8 days Destinations Montepulciano, Pienza, Bagno Vignoni, Montalcino, Buonconvento, Siena Age Range Ages 16+ Operated in Only: German Physical Rating Easy Distance 36 mi Operator ASI Reisen From
20% Off- US$1,138
Walk self-guided trails from Florence through the Chianti landscape to UNESCO-protected Siena, passing hilltop towns like Castellina in Chianti and vineyard estates with wine tastings along the route. Cover moderate-level paths westward to UNESCO-listed San Gimignano's medieval towers and the Etruscan fortress town of Volterra, walking 100+ km over 6 days with luggage transfers between accommodations. Finish by following the ancient Via Sale salt traders' route through pine forests and coastal hills to the turquoise waters of Cecina Mare on the Tuscan coast.
Duration 8 days Destinations Florence, Greve in Chianti, Tuscany, Castellina in Chianti, Panzano, Siena, Marina di Campo, San Gimignano, Volterra, Marina di Castagneto CarducciSee all destinations Age Range Ages 16+ Operated in Only: German Physical Rating Moderate Distance 423 mi Operator ASI Reisen From
20% Off- US$1,581
Walk 6 km through the terraced vineyards of UNESCO-listed Chianti, starting at Badia a Passignano Monastery and finishing at Vicchiomaggio Castle, where you'll taste Chianti wines with views over the hills. In Florence, cover 10 km on foot from Piazzale Michelangelo, passing hidden Romanesque churches and the lively Porcellino covered market. Take on an optional 12 km mountain trek up to Lake Scaffaiolo at 1,500 meters elevation, then cross Italy's second-longest suspension bridge near Pistoia.
Duration 8 days Destinations Pistoia, Tuscany, Florence, Vinci, Lucca Age Range Ages 18+ Physical Rating Easy Distance 212 mi Operator Just You From $2,213
9% Off- US$2,011You save $201
Hike from Settignano to the hilltop town of Fiesole with views over Florence's Duomo and Palazzo Vecchio across Chianti's rolling hills. Walk from Badiaccia Montemuro to Radda in Chianti, passing vineyards and medieval hamlets like Panzano along scenic trails. Stay at Hotel Palazzo San Niccolò in Radda and follow self-guided routes with GPS data, covering moderate terrain suitable for ages 16+.
Duration 8 days Destinations Florence, Fiesole, Greve in Chianti, Panzano, Radda in Chianti, Siena Age Range Ages 16+ Operated in Only: German Physical Rating Moderate Distance 43 mi Operator ASI Reisen From
9% Off- US$1,325
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 in 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."