Italy · Tuscany
Eight days through the Apennines and the white roads of Tuscany.
About this tour
This Tuscany gravel cycling holiday crosses Italy from north-west to south-east — Pisa to the Maremma coast — almost entirely on unpaved roads. Six riding stages, 450 to 615 kilometres depending on route choice, with 7,000 to 11,000 metres of cumulative climbing. A proper gravel tour of Tuscany, not a sightseeing loop with bikes.
The first two days follow the southern flank of the Apennines through the Arno valley past Lucca and Pistoia into Florence. From there the route turns south into Chianti — rolling clay hills, narrow white gravel roads, cypress alleys and vineyard lanes — through Greve in Chianti, San Gimignano and Siena, all hilltop towns with towers built by merchants who wanted their wealth seen from miles away.
The white gravel under your wheels is not just a road surface — it is Tuscany's signature. You ride through hills that Renaissance painters used as backgrounds. The cypress trees. The old stone farms. The vineyards in September light.
Route overview
460–615 km · 5,000–9,950 m total · Pisa → Marina di Grosseto, Italy
What you get
Mostly unpaved — white gravel roads and farm tracks that cars cannot reach.
Seven nights in farm hotels and boutique stays, chosen for location and food.
Six stages through Chianti wine country end at a spa hotel on the Tyrrhenian coast — a swim in the Mediterranean and a gala dinner at the end of the road.
Day by day
Bikes built or collected at Pisa airport and a welcome briefing at a café. Adventure follows the flat Serchio river; Explorer climbs ~10 km toward Monte Serra (~800 m) and drops to Lucca for lunch. Both finish along the Valdinievole marshland lanes to Pescia.
Adventure runs the Arno valley into Florence. Explorer takes another ~10 km climb toward Pistoia through the plant-nursery valley, a short hike-a-bike, then a fast descent to the Arno. Both arrive with time to walk the city.
South into the Chianti Classico zone — clay hills, olive groves and the first Strade Bianche, cypress alleys lining the approach to each hilltop town. Explorer adds a forest singletrack detour before the climb into San Gimignano.
A loop of San Gimignano's towers, then white gravel and forest paths past ridgetop hill towns. The steepest climb of the tour leads into Siena; the hotel sits on a hillside with a pool and panoramic view — two nights.
A genuine rest day. Keep moving with guided Chianti loops on Strade Bianche through Radda, Gaiole and Lecchi, or rest — Siena's old town is 10 km away, vineyard visits can be arranged, the pool is there.
The queen stage. South through the Crete Senesi, then up into Brunello di Montalcino country and on toward Monte Amiata. Long climbs, long descents, no technical difficulty — just fitness and pacing. Castel del Piano sits above 600 m.
A ridge crossing, then a long descent through the Maremma to the Tyrrhenian coast. The tour finishes at a beach spa hotel: a swim in the Mediterranean, cold drinks and a gala dinner.
Early bus from Marina di Grosseto to Pisa airport (about 2.5 hours). Extra nights at the spa hotel are possible, or travel onward by rail to Florence, Bologna, Venice, Milan or Rome.
How we ride
Follow the guide across the passes and long descents. The support vehicle is positioned at key points, navigation and logistics are handled — you focus on the riding.
Load the day's route and set off when you're ready — you control the breaks and stops. The crew is positioned along the route and meets you at the hotel each evening.
Every tour is run in English — guiding, daily briefings, route notes and all documents are in English.
What's included
Common questions
The Adventure route suits riders comfortable with 3–4 hours in the saddle over consecutive days — at home on a gravel bike in hilly terrain, but no need to race. The Explorer route asks more: 5–6 hour days, up to ~2,000 m of climbing per stage, and the confidence to navigate loose gravel and forest tracks independently.
A gravel bike (mechanical or e-assist), or a light MTB with suitable tyres and gearing — road bikes and hybrids aren't suitable. Minimum 38 mm tyres (wider is better), tubeless strongly recommended for Tuscany's dry vegetation and summer thorns, and a low gear around 0.9 for the steeper climbs. Have it freshly serviced before you travel.
Yes — we can arrange a gravel bike or e-bike through a local partner in Pisa, ready at the airport on arrival and returned at the end. Rental is an additional cost; ask us about specifications before booking.
Both, daily. An English-speaking guide leads each day, and GPS files (Garmin, Wahoo, Komoot) are provided so you can ride at your own pace. Most riders mix the two; the support vehicle follows the route regardless.
Tuscany's white gravel roads are a mix of compacted limestone and clay — generally rideable on standard gravel tyres, smooth in places, loose in others depending on season and weather. The Chianti stages hold the most iconic sections: fast and firm when dry, sticky after rain.
Most of our riders are 45–65. Sensible daily distances, a genuine rest day, the daily Adventure/Explorer choice and the option of the support vehicle let you calibrate it to how you feel. Cycling fitness and multi-day experience matter more than age.
Yes — many riders come solo. Groups are up to 10 per guide and typically international. Accommodation is a shared double room by default; a single-room supplement is available.
Before you go
Fly to Pisa (PSA). We organise a shared transfer from the airport to the start on day 1. On the final day, a transfer runs from Marina di Grosseto to Pisa airport (about 2.5 hours) — plan return flights no earlier than 14:00. Rail connections from Pisa Centrale are available if you prefer to arrive independently.
Bring a gravel bike (mechanical or e-assist) or a light MTB with suitable tyres and gearing — road bikes and hybrids aren't suitable. Minimum 38 mm tyres (40–45 mm better), tubeless strongly recommended, and a low gear around 0.9 for the steeper climbs. Have it freshly serviced before you travel and carry a spare tube. Rental can be arranged through a local partner — ask when you book.
Comprehensive travel and accident insurance — including medical cover and repatriation — is required and not included. Take out cover that includes cycling before you travel; ask us if you'd like a recommendation.
Pack for warm days and cool evenings — September departures can still see 10–12°C in the hills, so a light packable layer earns its place. Towels and toiletries are provided. Off-bike: one pair of comfortable walking shoes and something smart-casual for dinner.
Intermediate — challenging. This tour is graded Explore & Adventure. You don't need to race, but you should be comfortable riding back-to-back days on mixed terrain. A good benchmark is 70–80 km with 1,000–1,200 m of climbing with energy to spare. See our levels page, or get in touch if you're unsure.
When to go
| Dates | Availability | Price per person |
|---|---|---|
| 2026 | ||
| 4 – 11 Sep 2026 | Sold out | From €2,790 |
| 2027 | ||
| 4 – 11 Jun 2027 | Open | From €2,790 |
| 3 – 10 Sep 2027 | Open | From €2,790 |
Per person, shared room. Single supplement on request. A deposit secures your place; the balance is due 60 days before departure.
Private & group tours
A cycling club, a group of friends or colleagues — we can arrange a private departure on dates that suit you, same route and same support, just your own group. We also run fully custom private tours for smaller groups.
Also worth considering
Stay in the loop
New routes, trip reports and quiet-season departure alerts — before anyone else. No spam, just the good gravel.
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