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 Walking and Wine
- Geluxe: Italy: Tuscany and Umbria Vineyard Walks
- Walking Northern Tuscany
- Tuscany Walking & Hiking Tour
- Best of Chianti: Walk & Wine
- Tuscany: hilltop towns of Val d’Orcia & Siena (Self-guided Walking Tour)
- Walking Trails of Hidden Tuscany
- Essential Tuscany - Land Only
- Under the Tuscan sun - from Siena to Cortona (7 days)
- Grand Tour of Tuscany 7 Days
Tuscany Walking and Wine
23 Reviews by TourRadar travelers“The scenery was stunning and it was very well organized. You can't beat the scenery you experience!”
Bryan, traveled in March
Duration 8 days Destinations Pisa, San Gimignano, Castellina in Chianti, Tuscany, Pienza, Siena, Montalcino, San Quirico D'orcia, Florence Age Range Ages 16+ Physical Rating Moderate Distance 313 mi Operator Explore! From $3,040
7% Off- US$2,830You save $210
Geluxe: Italy: Tuscany and Umbria Vineyard Walks
1 Review by TourRadar travelers“I will be talking about this trip for years to anyone who will listen. Could not be happier!”
Melissa, traveled in May
Duration 8 days Destinations San Gimignano, Colle di Val d'Elsa, Monteriggioni, Panzano, Greve in Chianti, Siena, Val d'Orcia, Pienza, Montepulciano, Rome Age Range Ages 18+ Physical Rating Easy Distance 171 mi Operator G Adventures From $4,599
20% Off- US$3,679You save $920
Walking Northern Tuscany
151 Reviews by TourRadar travelers“Beautiful scenary! Each hike was very different. Food at the farmhouse was lovely and the dogs Elvis and Dora are great company on the walks.”
Janet, 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 Castelnuovo di Garfagnana, Castiglione di Garfagnana, Lucca, Pisa, Cinque Terre, Florence, Tuscany Age Range Ages 16+ Physical Rating Moderate Distance 217 mi Operator Exodus Adventure Travels From $2,803
25% Off- US$2,115You save $688
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
25% Off- US$4,169
Duration 5 days Destinations Greve in Chianti, Panzano, Radda in Chianti, Gaiole in Chianti Age Range Ages 18+ Physical Rating Easy Distance 11 mi Operator Bookatrekking From
25% Off- US$794
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 
San Quirico d'Orcia serves as the base for daily guided walks through Tuscany. Paths lead through Montalcino's vineyards to Sant'Antimo Abbey, the thermal town of Bagno Vignoni, and scenic ridgelines overlooking Val d'Orcia, with stays at Hotel Albergo Palazzuolo featuring authentic Tuscan dining.
No departure dates availableDuration 8 days Destinations San Quirico D'orcia, Bagno Vignoni, Montalcino, Castelnuovo dell'Abate, Montepulciano, Monticchiello, Pienza, San Gimignano, Monteriggioni, Val d'OrciaSee all destinations Age Range Ages 18+ Distance 133 mi Operator HF Holidays 
Walk the Via Larentia pilgrimage route through Tuscany's Crete Senesi region, covering 15-23km daily across rolling clay hills with cypress-lined roads and farmhouses between Siena and Cortona. Hike through the Biancane di Leonina's colored ravines, then relax in thermal baths at Rapolano hamlet after crossing clay terrain. Climb 360m up to medieval Cortona for views over Valdichiana valley. Taste Brunello and Rosso di Montepulciano wines in hilltop villages while staying in selected 3-4 star hotels and inns. Luggage transfers are included on this self-guided moderate trek for ages 16+.
Duration 7 days Destinations Siena, Asciano, SI, Serre di Rapolano, Montepulciano, Cortona Age Range Ages 16+ Operated in Only: German Physical Rating Moderate Distance 46 mi Operator ASI Reisen From
25% Off- US$1,055
Duration 7 days Destinations Pisa, Casciana Terme, San Gimignano, Colle di Val d'Elsa, Siena, Radda in Chianti, Panzano, Greve in Chianti, Impruneta, Florence Age Range Ages 16+ Operated in Only: German Physical Rating Moderate Distance 100 mi Operator ASI Reisen From
25% Off- US$1,017
What people love about Hiking & Trekking Tours in Tuscany
- Tuscany Walking and Wine
For the most part it was well planned and the walks and accommodations were good. The last night in Florence the accommodations were poor.
- 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 Walking & Hiking Tour
I can't say enough about Caspin Journeys. The hosts were wonderful and made us feel like family right away. So well organized and planned out. The views were incredible along the way and even though there was a lot of walking, the pace was comfortable. Every detail was planned perfectly. The food was outstanding, and the small group size made it easy to get to know everyone. Would definitely recommend this tour company to anyone thinking of going to Europe.
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."