Not every walking holiday needs to consume a fortnight of annual leave. Some of the most satisfying journeys happen in the space of a long weekend, or in those few extra days that appear when a public holiday falls conveniently mid-week. The question is simply knowing where to go and which route to choose.
Tuscany is one of those rare places where the landscape is dense enough with interest that even three or four days on foot feel genuinely complete. You are not skimming the surface. You are walking through one of the most carefully cultivated and historically layered regions in Europe, and the experience of doing so at a slow pace, with your luggage transferred ahead and your accommodation pre-booked, is available in formats that fit a working life.
Below are three walking holidays we organise in Tuscany that suit shorter windows of time. Two are true long weekends. The third is honest about what it requires: it is eight days, and we say so clearly, but for anyone who can stretch a public holiday into a longer autumn break, it belongs on this list.
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Part of what makes Tuscany so well suited to short walking holidays is its geography. The region is compact, well-connected by rail, and structured around a series of distinct landscapes that can each be explored in a few days without any sense of incompleteness. You can arrive in Florence by train from most major Italian airports and be walking in the Chianti hills within an hour and a half. The same is true of Siena, Pisa, and San Miniato.
Autumn is a particularly good season for walking in Tuscany. From September through to October, temperatures are cooler than in midsummer, the light is lower and warmer, and the landscape carries the colours of the harvest. The walking conditions on routes like the Chianti Hills and the Via Francigena are generally more comfortable in this period than in July or August, when some sections offer little shade and temperatures can climb considerably.
One practical note on seasonality: all three itineraries described below are available through October. If you are planning around a late-autumn public holiday, please check current availability directly with us, as some accommodation along these routes operates seasonally and closing dates can vary from year to year.
At a glance: 5 days / 4 nights | 40 km | Level 2 | April to October | from €404
Of the three options here, the Chianti Hills walking holiday is the one that most closely matches the idea of a long weekend, provided you can take a couple of extra days around a public holiday. Five days is not a fortnight, and the route is compact enough to feel contained rather than demanding.
The itinerary runs between Greve in Chianti and Siena, passing through Radda in Chianti along the way. The terrain follows the strade bianche, the unpaved white roads that cross the Chianti Classico zone, as well as forest paths through oak and chestnut, and vineyard tracks between the hilltop villages that define this part of Tuscany. The total distance of 40 kilometres is spread across the walking days, making the daily stages manageable for walkers of moderate fitness.
Day 1: Arrival in Greve in Chianti, with optional loop walks of 9, 10 or 12 km through the surrounding vineyards and hills
Day 2: A choice of routes from Greve, exploring the landscape at your own pace
Day 3: A car transfer takes you to Monte San Michele; the walk begins from Badiaccia, descending through century-old chestnut forest to Volpaia and on to Radda in Chianti (14 or 12 km depending on the variant)
Day 4: A scenic loop around Radda, passing through the hamlet of Vertine and the Colle Bereto vineyard (17 km), then a bus or private transfer to Siena
Day 5: Departure from Siena
The route is rated Level 2, meaning it is suited to walkers with some experience of multi-day walking, though no specialist skills are required. Luggage is transferred between hotels throughout.
Siena, where the walk ends, is one of Italy's most complete medieval cities. The Piazza del Campo and the Duomo alone justify arriving a day early or leaving a day late.
This is a Tuscany walking holiday built around the Chianti Classico landscape, and it is genuinely suited to anyone who wants to spend five autumn days walking through one of Italy's most celebrated wine-producing regions without committing to a longer expedition.
The Via Francigena is the historic pilgrimage route connecting Canterbury and Rome, and its Tuscan section divides naturally into shorter journeys. For travellers with a long weekend available, we offer two standalone itineraries that each cover a distinct portion of this route. They share the same landscape and the same road, but they are different journeys, suited to different priorities.
The San Miniato to San Gimignano weekend is the shorter of the two, and the one that fits most naturally into a standard long weekend. Three days, two nights, 37 kilometres. It begins in San Miniato, a hilltop town in the Val d'Elsa that sits above the Arno plain and has been a waypoint on the Via Francigena since the Middle Ages. The route then crosses to Gambassi Terme before arriving at San Gimignano, the UNESCO World Heritage Site whose medieval towers are one of the most recognisable silhouettes in Tuscany.
The walking is rated Level 2. The terrain crosses the Val d'Elsa landscape with its characteristic mix of vineyards, olive groves, and open hillsides, passing through the thousand-year-old Pieve di Chianni at Gambassi Terme, associated with Archbishop Sigeric's recorded journey along the Via Francigena in 990 AD. The final day's walk of 13.5 km brings you into San Gimignano, where the towers announce your arrival from some distance before you reach the walls.
This is a genuinely complete short walking holiday. The route has a clear narrative arc, and San Gimignano is a satisfying place to finish. An extra night in San Gimignano can be added if you want more time to explore the town.
The San Gimignano to Siena weekend is four days, making it a long weekend rather than a standard one. It picks up where Option A leaves off and continues south along the Via Francigena through Colle di Val d'Elsa and Monteriggioni before arriving in Siena.
Monteriggioni is one of the highlights of this section: a small walled village that has survived almost entirely intact since the thirteenth century, and one of the most striking places along the entire Tuscan Via Francigena. From there, the final stage into Siena follows dirt roads along the Montagnola Senese before the city's medieval gates come into view. Siena itself, with its Piazza del Campo and Gothic cathedral, is a destination in its own right and a very satisfying place to end a walking holiday.
The itinerary is described as suitable even for those approaching their first walking holiday, which makes it one of the more accessible options in our Tuscany programme.
San Miniato to San Gimignano
3 days / 2 nights | 37 km | Level 2
Finishes at San Gimignano (UNESCO World Heritage)
Best for a standard long weekend
From €233
San Gimignano to Siena
4 days / 3 nights | Approx. 45 km | Suitable for first-timers
Finishes in Siena (Piazza del Campo), via Monteriggioni
Best for a long weekend plus one day
From €400
If your priority is fitting the walk into a Friday-to-Sunday window, Option A is the cleaner choice. If you can take Monday as well, Option B rewards you with Monteriggioni and Siena, which together make for a more substantial conclusion.
It is also worth noting that the two itineraries connect. If you have a full week available, walking San Miniato to Siena in one continuous journey is possible, and we can organise this as a complete Via Francigena short break through the heart of Tuscany.
At a glance: 8 days / 7 nights | 75 km | Difficulty Level 3 | April to October | from €1,061
This one requires honesty. The St Francis Way from Florence to Chiusi della Verna is an eight-day journey, and it is not a long weekend by any reasonable definition. We include it here because autumn in Italy brings a number of public holidays, and there are years when those holidays fall in ways that allow travellers to combine them with annual leave and arrive at something approaching ten or eleven days away. For those people, this is the walk.
The route follows the Via di Francesco, the Way of St Francis, from Florence eastwards into the Apennines. It is a fundamentally different kind of Tuscany to the Chianti Hills or the Via Francigena: less vineyard, more forest; less medieval town, more mountain landscape. The route passes through the Foreste Casentinesi National Park, the Hermitage of Camaldoli, and the village of Stia in the Casentino valley before arriving at the Sanctuary of La Verna, the Franciscan site in the Apennines where St Francis is said to have received the stigmata.
The difficulty is rated Level 3, which means some experience of mountain terrain is recommended. This is not a beginner's walk. The stages are longer and the elevation gain more significant than on the Chianti or Via Francigena itineraries. That said, SloWays organises all accommodation, luggage transfers, and route documentation, so the logistical side of the journey is fully supported.
The itinerary includes pre-booked accommodation, luggage transfer between stages, detailed route notes and GPS navigation via the SloWays app, and 24-hour phone assistance. Medical and luggage insurance is included. For the full list of what is and is not included, see the itinerary page.
The best window for this walk, according to our own seasonal guidance, is late April to early June or mid-September to mid-October. Autumn conditions in the Apennines can change quickly, and walkers should be prepared for rain, mist, and lower temperatures at altitude, particularly later in the season.
If eight days feels like too much, it is worth knowing that the Via di Francesco is structured as a series of standalone stages. The Florence to La Verna section is Stage 1 of a longer route that continues through Umbria to Rome. It can be walked on its own, as described here, without any commitment to continuing further.
The three itineraries are distinct enough that the choice usually makes itself once you know how many days you have and what kind of landscape you are drawn to.
Chianti Hills
5 days | 40 km | Level 2
Vineyards and hilltop villages, Greve to Siena
From €404
San Miniato to San Gimignano (Via Francigena)
3 days | 37 km | Level 2
Val d'Elsa landscape, medieval villages
From €233
San Gimignano to Siena (Via Francigena)
4 days | Approx. 45 km | Beginner-friendly
Val d'Elsa, Monteriggioni, Siena
From €400
Florence to La Verna (Via di Francesco)
8 days | 75 km | Level 3
Apennine forests, Foreste Casentinesi National Park
From €1,061
A few pointers to help narrow it down:
If you have a standard long weekend (Friday to Sunday): the San Miniato to San Gimignano walk is the most straightforward fit. Three days, a clear finish at San Gimignano, and a price that makes it easy to justify as a spontaneous autumn trip.
If you can take Monday off: San Gimignano to Siena adds Monteriggioni and one of Italy's great medieval cities to the equation. It is also the most accessible of the four in terms of walking experience required.
If you have five days and want the Chianti landscape: the Chianti Hills walk delivers a fuller picture of the region, with more time in the vineyards and a finish in Siena.
If you can extend a public holiday into a longer break: Florence to La Verna offers a more demanding journey through the forested landscapes of the Apennines and the Casentino.
All four itineraries are self-guided, meaning you walk independently with route notes, GPS navigation via the SloWays app, and pre-arranged logistics. There are no fixed departure dates to fit around; you choose when to start, and we organise the rest.
Autumn availability across these routes runs through October, though we always recommend confirming specific dates directly, particularly for the Florence to La Verna walk, where accommodation at higher elevations can close earlier in the season.
If you are weighing up which walk to book, or want to discuss combining stages or adjusting the itinerary, our team is available to help. You can browse all our Tuscany walking holidays and request a personalised quote based on your dates, group size, and preferred room type. Short walking holidays in Italy are not a compromise. Sometimes three or four days on foot, in the right place, at the right time of year, is exactly enough.
Written by the SloWays Team
Nominee Best Specialist Tour Operator 2026
