Hill Towns of Tuscany : Montepulciano to Siena
About this trip.
It's a week on foot from Montepulciano to Siena, walking inn to inn across the hill towns of southern Tuscany.
Hill towns and the walk between them
The towns of southern Tuscany sit up high — that is the whole reason they exist, having been built defensively in the medieval centuries. Days on this route involve climbing out of one valley, crossing the cultivated land between, and arriving at the next town on foot through an old gate rather than rolling up by coach. It is a different way of meeting these places, and an unhurried one. Eight days is enough for the rhythm to settle.
The landscape between is the postcard one: cypress avenues, vineyards, wheat fields. It is genuinely beautiful, and in high summer it is also well-walked and well-driven. The footpaths keep you off the main roads for most of each day; the towns themselves are where you'll cross paths with other visitors.
How the week works
Montepulciano sits at one end and Siena at the other, with a string of smaller hill towns between them. The format is self-guided and inn-to-inn: you walk during the day, your luggage is moved on ahead, and a room is waiting at each evening's stop. There is no group, no leader, no fixed pace beyond getting yourself from one bed to the next. Macs Adventure supplies the route notes, the maps and the booked accommodation; you supply the legs and the appetite.
The arc of the route — south to north, ending in Siena — gives the week a sense of build. You finish in one of the great Tuscan cities rather than passing through it on day three, which is a more satisfying shape than it sounds on paper.
Bookings and what's included
The trip runs over eight days and seven nights, with prices from £1,385 per person. That covers the accommodation along the route, the luggage transfers between hotels, and the route information you need to navigate the days yourself. Flights, transfers to Montepulciano and out from Siena, and meals beyond breakfast sit outside the package — the format assumes you are happy to handle your own travel to the start and to choose where to eat each evening.
It suits walkers who want a structured route without a guide, who are comfortable with a few hours on their feet each day across rolling rather than alpine terrain, and who would rather sleep in a different town each night than base themselves in one place. If you want everything decided for you, this is not quite that. If you want the freedom of a self-guided week with the logistics taken off your hands, it is the format at its most workable.
The shape of the trip.
What's typically in the price, what isn't.
A general guide for walking 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 walking day
- ✓Detailed route notes with maps and GPX files
- ✓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 (strongly recommended)
- ×Lunches — typically a village picnic or café stop
- ×Some evening meals — depends on the specific itinerary
- ×Alcohol beyond any wine included with set dinners
- ×Optional room or transfer upgrades
Everything you might be wondering.
Q1How hard is it really?
The grading is set by the operator and usually reflects daily distance and total ascent. As a rule of thumb: if you can comfortably manage a 5-6 hour hillwalk at home on a weekend, a moderate-graded route will be fine. Read the day-by-day notes carefully, and train with a loaded pack in the months before.
Q2Can I do this solo?
Yes — self-guided walking holidays are well suited to solo travellers, and some operators waive the single-room supplement on certain departures. The route notes are written for confident independent walkers, and most operators run a 24/7 support line.
Q3Do I need to speak the language?
No. Hotels and restaurants on the route are used to English-speaking walkers. A phrasebook for menus and a few polite basics (hello, thank you, please) is all you really need. The operator's support line speaks English.
Q4Can I bring my dog?
Some routes are dog-friendly, others aren't — it depends on whether all the accommodation on the itinerary accepts dogs. Check with the operator before booking. If you do bring a dog, you'll need a pet passport, up-to-date rabies vaccination, and a lead for villages.
Q5What if it rains?
The route is walkable in rain — your luggage travels ahead regardless, so you'll always arrive somewhere dry. Some trails get slippery in wet weather and the operator's support line can arrange a taxi for any stage if conditions are properly bad.
Q6How do I get there from the UK?
Most routes are reachable by a short flight to a nearby airport, followed by train or transfer. The operator will usually point you at the nearest airport and can advise on rail connections. Some will book train tickets on your behalf for a small fee.
Q7Can I shorten or extend it?
Usually yes. Many operators offer shorter versions of a route as a standalone, and most will add extra nights at the start or end at their own rates. Ask when you enquire — they'll tailor it before booking.
Q8What about cancellation?
Typically 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 is strongly recommended.
Three walking holidays, side-by-side.
Other walking holidays on Mooch in the same spirit. All prices per person, from the operator.
