About this trip
Eight days walking between Pisa and Florence on gravel strade bianche, through the kind of Tuscany you picture before you've even been — rolling hills, cypress lines and vineyards running out from medieval hilltop towns.
Walks are graded leisurely to moderate, with real gaps built in for long lunches, wine and afternoons by the pool rather than a route that just ticks off distance. Along the way you stop in Chianti and the Val d'Orcia, with visits to San Gimignano, Pienza and Montalcino, and wine tastings at family-run, often organic producers.
Siena's traffic-free old centre gets a proper look, and the tour ends with a free day in Florence to spend as you like — Duomo, Uffizi, Ponte Vecchio, or just wandering.
What you'll do
- Walk gravel strade bianche trails from Pisa toward Florence through Chianti vineyards
- Taste Chianti Classico, San Gimignano Vernaccia and Brunello di Montalcino at family-run wineries
- Explore San Gimignano's medieval towers and spend three nights in UNESCO-listed Pienza
- Hike through the Val d'Orcia to Montalcino
- Wander Siena's traffic-free medieval centre and Piazza del Campo
- Free day in Florence to explore the Duomo, Uffizi and Ponte Vecchio at your own pace
- Walks range from leisurely to moderate, with plenty of time for meals, wine and pool afternoons rather than a packed hiking schedule
- Suits travellers who want walking and wine in equal measure, not a serious trekking trip
Worth it if you want stunning Tuscany landscapes with good wine and accommodation. Think twice if you're a serious hiker or expect consistent accommodation quality.
- Guide Enrico was standout, going above and beyond to meet everyone's needs despite mixed hiking abilities.
- Landscape, towns, and wine tastings are genuinely excellent; Pienza particularly lovely, new highlights each day.
- Mixed hiking abilities meant walks felt slow; hike descriptions didn't match actual difficulty or terrain.
- Only one or two wine tastings included despite tour name; Friday tasting costs extra and worth budgeting for.
Distilled from real traveller reviews on TourRadar — we don't edit out the bad bits.
The same-vibe trips, side by side — price, value per day, and how each is moving. Only we can lay two operators' trips out honestly.
Sorted by fit — never by who paid. Price moves and fill fill in from our own tracking as it builds.
Departing in Oct is cheapest — from £1,925, about 18% below the priciest month (Sep).
Getting there
Opens Trip.com, pre-filled — one-way so you can book your return whenever. Prices & booking shown there.
Where to stay
A night before your tour in Pisa · 3 Oct – 4 Oct
Booked on their own sites, separate from your tour. We may earn a commission — it never changes your price.
Sort the essentials
Partner offersWe may earn a commission from partner offers. It never changes your price or our ranking.
More trips like this
Ranked on real fit — in case this one isn't quite yours.
Booked with the operator via TourRadar · we may earn a commission.
Want longer in Italy?
Working holidays, volunteering & more — £50 off with code 18TO35TRAVEL.
Powered by Global Work & Travel · we may earn a commission on bookings.