About this trip.
Tuscany at a leisurely pace
Castellina in Chianti is where the week begins — an old hilltown above the vineyards, known as much for its Etruscan sites as for its wine cellars. This eight-day self-guided loop puts you there for the first night, then sends you south through the Chianti hills and into the Crete Senesi, the wave of pale clay ridges that gives the country south of Siena its distinctive look.
The riding is leisure-graded rather than sportive. Terrain is undulating — cypress-lined climbs, descents past olive groves and stone farmhouses, the occasional pitch up to a walled town — but the days are paced for someone who wants a long lunch and still time to wander before dinner. E-bikes are offered as an alternative to standard hire bikes, and most riders who choose the assist do so for the climbs rather than the distance.
The route through the hill towns
From Castellina, the week heads west to San Gimignano, the medieval skyline of towers that earns it its UNESCO listing and, in high season, its share of coach traffic. From there the route continues to Monteriggioni — a small, fully walled village above the road to Siena — then on through Buonconvento and Asciano in the Crete Senesi, finishing in Siena itself. The connecting roads are mostly quiet and rural, threading through forests, alongside rivers and across open ridge country between the vineyards of Chianti and the wine villages around Montalcino and Montepulciano.
Accommodation is in Tuscan farms and small hotels rather than chain properties, and meals tend to be regional and unhurried. Wine tasting isn't bolted on as an excursion — it's what happens when you stop for the night in this part of Italy.
Bookings, bikes and the practical side
The trip opens with a transfer from Pisa Airport to Castellina in Chianti, around an hour and a half by road. A local representative meets you on arrival or the following morning to fit your hire bike and run through a welcome meeting; from there the riding is independent, and you make your way through the week at your own pace with the accommodations booked ahead. Prices start at £1,495 per person, with e-bike hire available as an add-on at booking.
It suits couples and friends who want some independence on the bike but no responsibility for logistics, and who would rather end the day at a Tuscan farmhouse than a city hotel. If you'd like a proper evening or two in Siena, build in extra nights — the standard itinerary arrives there at the end of the week, when most riders are heading home.
The shape of the trip.
What's typically in the price, what isn't.
A general guide for cycling holidays of this kind. Check the operator's booking page for the final inclusions on this specific trip.
Typically included
- ✓Hotel accommodation, double or twin en-suite rooms
- ✓Daily breakfast at each hotel
- ✓Luggage transfer between hotels on every riding day
- ✓Bike rental (usually a hybrid), helmet, and panniers
- ✓Detailed route notes with GPX files and emergency contacts
- ✓24/7 support line in English for the duration of the trip
Typically not included
- ×Flights to and from the country of travel
- ×Travel insurance with cycle cover (strongly recommended)
- ×Lunches and most evening meals — eat locally on the route
- ×E-bike or road-bike upgrades (usually a supplement)
- ×Repair kit consumables (tubes, chain lube) beyond what comes with the bike
- ×Any alcohol beyond wine included with set dinners
Everything you might be wondering.
Q1How hard are the climbs?
Grading reflects daily distance, total climbing, and traffic. Moderate routes typically involve 40-60km a day with 300-600m of climbing, on quiet roads or well-surfaced bike paths. If you ride regularly at home and can manage a 40km weekend ride, you'll be fine. Check the daily elevation profile when the operator shares it.
Q2Is bike rental included?
It's usually included, with a hybrid as standard and an e-bike or road-bike upgrade available for a supplement. Helmets and panniers normally come with the rental. Check the operator's booking page for the exact inclusions on this trip.
Q3What if I get a puncture?
Rental bikes come with a small repair kit and a pump. If you can't fix it yourself, the operator's support line can arrange a replacement or a lift to the next hotel — times vary by location. Carry a phone and the support number at all times.
Q4Can I use my own bike?
Yes, most operators are happy for you to bring your own bike — you'll often get a small discount off the trip price in lieu of rental. Check with the airline on how to transport it, and bring basic spares (tubes, multi-tool).
Q5Can I do this solo?
Absolutely — self-guided cycling holidays work well for solo travellers. The route notes, GPX files, and 24/7 support are designed for confident independent riders.
Q6What if the weather is bad?
The route is rideable in rain if you're dressed for it, though some surfaces get slower. The operator's support line can reroute you onto a lower / flatter alternative or arrange a vehicle transfer for any stage if conditions are genuinely unsafe.
Q7How do I get there from the UK?
Fly into the nearest airport, then train or transfer to the start point. The operator will advise — some will book onward trains for a small fee. If you're bringing your own bike, check dimensions and dismantling requirements with the airline in advance.
Q8What about cancellation?
A deposit (usually 20-25%) is taken at booking, with the balance due 8-10 weeks before departure. The operator's own terms apply — Mooch doesn't handle the booking or refunds. Travel insurance with cycle cover is strongly recommended.
Three cycling holidays, side-by-side.
Other cycling holidays on Mooch in the same spirit. All prices per person, from the operator.
