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2027 dates now available

Timeless Tuscany

Rolling hills and medieval towns
Iconic Tuscany | Walk along strade bianche, through sweeping countryside and olive groves.
Colle di Val d'Elsa | Your base for the week – a traditional town along the Via Francigena.
Elegant accommodation | Stay in the high-quality, comfortable Relais Della Rovere.
Varied walking | Either from the door or easily accessible by public transport.
Delightful day trips | Visit cultural hotspots like San Gimignano, Siena, and Florence.
What is included
  • 7 nights
  • 3 dinners & 7 breakfasts
  • route notes
  • GPS navigation
  • Timeless Tuscany
    Rolling hills and medieval towns
  • Strade Bianche – Tuscany’s iconic ‘white roads’
  • The turquoise waters of the Elsa River
  • Wander the cobbled streets of historic Volterra
  • The iconic towers of San Gimignano
  • A Tuscan dream – rolling hills, cypress trees, and lush vineyards
  • The walled town of Monteriggioni along the ancient Via Francigena pilgrimage route
  • Rural paths lined with wildflowers
  • Explore medieval Monteriggioni
  • Walking in the quiet countryside
  • Relais della Rovere – your enchanting hotel
  • Take a day trip to beautiful Florence
  • Tuscany is famed for its vineyards
  • Tuscan Schiacciata bread
What is included
  • 7 nights
  • 3 dinners & 7 breakfasts
  • route notes
  • GPS navigation

Holiday information

A walking holiday in Tuscany

With rolling hills draped in all shades of green stretching as far as the eye can see and ribbons of striking strade bianche (‘white roads’) winding through the countryside, Tuscany has a rustic beauty, storybook charm, and timeless feel.

There’s so much to see and explore here, and by spending the week in the traditional town of Colle di Val d'Elsa – one of the lesser-known hill-top towns of the region – you’re perfectly placed to walk the local trails and discover some of Tuscany’s hotspots, like the copper-coloured, medieval streets of Siena and the artistic city of Florence.
Your base for the week is the elegant Relais Della Rovere, a former cardinal’s residence built around the turn of the 12th century, which is now a high-quality, four-star hotel, just a 15-minute walk from Colle di Val d’Elsa’s main square. The town itself has a rich glassmaking heritage, a choice of local eateries, and a pretty, historic quarter, while the excellent bus network allows for easy day trips to its more famous neighbours, like San Gimignano and Volterra, where you can spend time soaking up the vibrant, bustling atmospheres of their medieval streets.

In contrast, Colle’s surrounding countryside feels like stepping into a serene pastoral painting. The quiet, flowing landscape rises and falls with the hills, neatly striped with vineyards and lined with cypress trees. Wander along the banks of the enchanting Elsa River (its turquoise waters starred with stepping stones), follow in the footsteps of ancient pilgrims along the Via Francigena, or simply take in the colours of the flourishing fields as you amble down country paths – there are many beautiful walks to enjoy here, both from the town and accessed by bus. This is the heart of rural Tuscany, in all its timeless glory.

And with no set itinerary and the promise of a peaceful retreat waiting for you in the evening, your days are as free as the hills.



Walking & more

The key to Inntravel holidays is flexibility. You can start on the day of your choice, and are free to add extra nights. There’s no fixed itinerary, so take your pick of our suggested walking and sightseeing options as the mood takes you.
  • The average maximum daytime temperatures and monthly rainfall relate to the nearest weather station and are intended as a guide only.
    Average temperatures and rainfall
      Jan Feb Mar Apr May Jun Jul Aug Sep Oct Nov Dec
    °C 9 11 13 17 21 25 29 28 25 20 14 10
    mm 65 63 60 65 58 41 30 43 69 76 103 69
  • An introduction
    Colle di Val d’Elsa is well situated for exploring Tuscany’s beautiful towns and countryside. There are plenty of walks to take – some from the town itself, others accessed by local bus (for which you’ll have to pay locally).

    We include notes for our own self-guided walking tours of Colle di Val d’Elsa, Volterra, Siena, and Florence too.
  • Choice of routes: 5.5km to 10.5km

    Colle di Val d’Elsa town trail: 5.5km, 2hrs
    Our self-guided route around Colle di Val d’Elsa heads through the lower town to join a meandering path up the hillside to the older part of town, where you can wander between the narrow, medieval streets and take in the scenic views. Returning back down the hillside, visit the Crystal Museum to learn about local glassmaking traditions (for which the town is known) and admire the exquisite creations on display.

    SentierElsa river trail: 8.5km, 3hrs; ascent/descent 225m
    This peaceful, circular walk starts off by following the banks of the Elsa River, with its stepping stones, bridges, and gorgeous turquoise colour (tinted by the limestone in the surrounding rocks). You reach a 15-metre-high waterfall, perpetually pouring into the large pool at its base, from which you loop back to Colle di Val d’Elsa through the countryside, traversing the bright strade bianche (‘white roads’) typical of the region, often lined with cypress trees. It’s on your way back through the lush fields that you gain a new perspective of Colle’s upper town, seeing it set within a beautiful countryside panorama, foregrounded by a small, wooded valley.

    Circuit north of Colle di Val d’Elsa: 10.5km, 4hrs; ascent 245m/descent 235m
    After a five-minute bus ride just to the edge of town (pay locally), you set off along quiet country lanes and strade bianche with far-reaching, classically Tuscan views – rolling hills, tall cypress trees, and silvery olive groves abound. You even catch a few glimpses of the extraordinary San Gimignano in the distance, its 14 surviving medieval towers like a mighty castle on the horizon, before the route descends to Colle di Val d’Elsa.

    Colle di Val d’Elsa to Poggibonsi: 10km, 4hrs; ascent 195m/descent 250m
    Walking north out of town along the old railway line from Colle di Val d’Elsa to Poggibonsi (now a tranquil walking and cycling path), your route shifts onto rural lanes which weave through quiet farmland, pretty meadows, and vineyards, passing the peacefully secluded Basilica di San Lucchese and its adjoining convent. Continuing on, you arrive at the Poggio Imperiale fortress, built around the turn of the 16th century and originally intended by Lorenzo the Magnificent, a member of the Medici family, as a new city, but it was never completed. Skirting the perimeter of these storied walls, you descend to the town of Poggibonsi, where your walk ends. From here, you catch the bus back to Colle di Val d’Elsa (pay locally) when you’re ready.
    Colle di Val d’Elsa town trail
    SentierElsa river trail
    SentierElsa river trail: 8.5km
    Circuit north of Colle di Val d’Elsa
    Circuit north of Colle di Val d’Elsa: 10.5km
    Colle di Val d’Elsa to Poggibonsi
    Colle di Val d’Elsa to Poggibonsi: 10km
  • Choice of routes: 9km to 14km

    San Gimignano
    You have a few options of walks from or around San Gimignano. You could simply catch a return bus here (pay locally) to have a look around the UNESCO-listed centre of this iconic town, taking in its timeless atmosphere as the mood takes you, or you could complete one of the following two routes:

    1. Around San Gimignano: 9km, 3.5hrs; ascent/descent 260m
    Accessing the town by return bus (pay locally), this circuit leaves the main streets via the Porta San Giovanni – a historic gate on the south side of the town walls, built in the 1200s. After an initial descent into glorious countryside, you climb up to the ridge on the far side of the valley to return to San Gimignano, marvelling at the fantastic views towards the town’s famous, imposing towers.

    2. San Gimignano to Colle di Val d’Elsa: 14km, 5.5hrs; ascent 320m/descent 500m
    Alternatively, after getting the bus into town, you can walk back to Colle di Val d’Elsa along part of the Via Francigena, an ancient pilgrimage route from Canterbury, England, to Rome. Just imagine the centuries of past pilgrims making the same journey, as you pass an understated yet beautiful abbey from the 13th century and wind your way through gentle rolling fields and olive groves.

    Colle di Val d’Elsa to Monteriggioni: 12.5km, 5hrs; ascent 245m/descent 225m
    This walk leads you to one of the best-preserved medieval towns in Italy – Monteriggioni – and, not only that, but it follows another section of the Via Francigena through the peaceful Tuscan countryside in a captivating blend of history and nature. You take a 10-minute bus ride to the start of the walk and return by bus from the wonderful walled town (both pay locally).
    Around San Gimignano
    Around San Gimignano: 9km
    San Gimignano to Colle di Val d’Elsa
    San Gimignano to Colle di Val d’Elsa: 14km
    Colle di Val d’Elsa to Monteriggioni
    Colle di Val d’Elsa to Monteriggioni: 12.5km
  • Each of these destinations can be reached by return bus, for which you’ll need to pay locally. Walk timings given are estimated without stops.

    Volterra town trail: 2.5km, 1hr
    Take in all the major sights of this fascinating hill-top town with sweeping views of the surrounding countryside from its elevated position. Volterra is rich in history, particularly from Etruscan times, and it boasts the atmospheric ruins of an ancient Roman amphitheatre.

    Siena city trail: 5.5km, 2hrs; ascent/descent 150m
    Romantic Siena is a medieval gem. The city’s historic centre is a UNESCO World Heritage Site, and the impressive Piazza del Campo feels like stepping back in time. Our self-guided city walk begins in this very square, before taking in other landmarks such as the striking cathedral (with its black-and-white-striped design), ancient fountains and marketplaces, and parts of the old city walls.

    Florence city trail: 6km, 2hrs
    Just an hour by bus from Colle di Val d’Elsa, Florence, the capital of Tuscany, is a must-visit for any trip to the region. Art and culture thrive here – the birthplace of the Renaissance – and our walking route through its graceful squares and narrow streets take in its historic palaces, grand public buildings, and the most famous art galleries.
    Volterra town trail
    Siena town trail
    Florence town trail

Accommodation

Your stay in Colle di Val d’Elsa is at the high-quality Relais della Rovere hotel, located just a short walk from the centre of town and within easy reach of the main bus station.
Relais della Rovere

Bedrooms

Extend your stay

Prices & travel options
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  • 7 Nights: 01 July 2026 - 31 October 2026 & 01 April 2027 - 31 October 2027

    Start any day | End by latest date(s) shown above

    Starting Price *
    1 - 31 Jul 2026 From £1108
    1 - 31 Aug 2026 From £1068
    1 - 30 Sep 2026 From £1083
    1 - 24 Oct 2026 From £897

    * Final price is subject to change due to the customisable nature of our holidays and is dependent on accommodation availability for the dates selected. We will contact you to confirm the final price. Single supplements are applicable on many of our holidays. Please contact us for full details.

    Includes accommodation, meals and services integral to the holiday as described, plus walking notes, but no travel from the UK, nor any connecting travel from the airport unless stated below.

    Book your flights through us and we'll find the best route and times to suit you. Please contact us to find out more about our flight booking service. We can also book connecting travel - see below.

  • RECOMMENDED AIRPORT(S):
    Florence or Pisa.
    As an alternative to flying, we can arrange rail travel from London.

    Travelling from the UK

    Travelling from outside the UK

    If you are flying from outside Europe,  If you are flying from outside Europe, we recommend flying via Florence or Pisa. To discuss onward connecting travel to the start of your holiday, please contact us. To discuss onward connecting travel to the start of your holiday, please contact us.

    Travelling from outside the UK
    We have many years' experience catering for customers who live outside the UK, and will be happy to make tailored arrangements to fit with your plans.

    You have two options:

    1) Book your own flights to London, from where we can book flights and onward connecting travel to your hotel.

    2) Book your own flights direct to an airport appropriate to your chosen holiday. You can either make your own way from the airport to the hotel, or we'll be happy to book onward connecting travel for you. Please consult with us before booking your flights, so that we can advise you on the suitability of your proposed route and timings.
    Outward route Airline
    Aberdeen - Florence (via Amsterdam Schiphol) KLM 
    Aberdeen - Pisa (via Amsterdam Schiphol) KLM 
    Outward route Airline
    Birmingham - Pisa jet2,  Ryanair 
    Birmingham - Pisa (via Munich) Lufthansa 
    Outward route Airline
    Bristol - Florence British Airways 
    Bristol - Pisa easyJet 
    Outward route Airline
    Nottingham East Midlands - Pisa Ryanair 
    Outward route Airline
    Edinburgh - Florence British Airways 
    Edinburgh - Pisa Ryanair 
    Outward route Airline
    Glasgow Prestwick - Pisa Ryanair 
    Outward route Airline
    Humberside - Pisa (via Amsterdam Schiphol) KLM 
    Outward route Airline
    Leeds Bradford - Pisa jet2 
    Leeds Bradford - Pisa (via Amsterdam Schiphol) KLM 
    Outward route Airline
    London City - Florence British Airways 
    Outward route Airline
    Gatwick - Florence British Airways,  Vueling 
    Gatwick - Pisa British Airways,  easyJet 
    Outward route Airline
    Heathrow - Florence British Airways 
    Heathrow - Pisa British Airways 
    Outward route Airline
    Luton - Florence Vueling 
    Luton - Pisa easyJet 
    Outward route Airline
    Stansted - Florence British Airways 
    Stansted - Pisa Ryanair 
    Outward route Airline
    Manchester - Florence British Airways 
    Manchester - Pisa easyJet,  jet2,  Ryanair 
    Outward route Airline
    Newcastle - Florence (via Amsterdam Schiphol) Air France 
    Newcastle - Florence (via Paris) Air France 
    Newcastle - Pisa (via Amsterdam Schiphol) KLM 
    Outward route Airline
    Teesside International - Pisa (via Amsterdam Schiphol) KLM 
    Travelling from outside the UK

    If you are flying from outside Europe,  If you are flying from outside Europe, we recommend flying via Florence or Pisa. To discuss onward connecting travel to the start of your holiday, please contact us. To discuss onward connecting travel to the start of your holiday, please contact us.

    This list of flight options should be used as a guide only, and you should check each airline’s website for current routes, frequency and schedules. Not all flights operate daily, and may not run for the entire season. You should also heed the latest flight arrival time and earliest flight departure time stated in the connecting travel section, as it may not be possible to arrange connecting travel outside these times. Please do not book your flights until we have confirmed your accommodation to you. Alternatively, our expert reservations team will be happy to offer advice and to make flight bookings for you for any of the options listed above. We charge £35 per person for our flight booking service. Your flights are then covered by our package-booking conditions, which give you greater protection in the event of delay or cancellation, as well as providing ATOL cover.

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Timeless Tuscany
7 nights
Timeless Tuscany
7 nights
Grade: Easy-to-moderate
Last fetch time is : 6/26/2026 2:42:06 PM

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