Walking from the towns of Buonconvento to Montalcino as part of a week-long trek through Tuscany, I was faced with a tough decision.

How many bottles of wine could I reasonably carry in my day pack?

The road that led to this quandary had passed right by the Caparzo winery – so naturally, we stopped in for a sample.

Now I weighed the taste of the award-winning Brunello against the realities of being only midway through our 14.5-kilometre walk on a warm day: a gruelling ascent up a steep grade to Montalcino still lay ahead.

I opted to carry only one bottle. Once it was packed away, we topped up our water and continued on, past rolling vineyards and along a short stretch of the Via Francigena, an ancient pilgrim route running from France to Rome.

It was another typical day on our self-guided trip walking from town-to-town in Tuscany's Val d'Orcia. If we could avoid encountering vipers and wild boar, we had nary a care in the world.

My husband and I had booked the tour through Girosole, which specialises in customised Italian walking tours.

Because the trips are private, we got to pick the departure date and duration. We opted for seven nights in five towns. On the other two days we were shuttled in one direction and walked in the other.

They handled all the logistics: hotel reservations, shuttles to and from the train, baggage transfers, detailed walking directions and even a mobile phone for emergencies.

Our responsibilities were few. We only needed to have our bags packed by 9 am, bring enough water, and try not to lose the directions. (After dropping them once on the roadside, I took a picture of them each day with my iPhone as a backup.)

Otherwise, we were free to walk and sightsee at our own pace. The directions, while not infallible, were very specific, including distances, landmarks, topography and the occasional marker from the Italian alpine club.

They also had useful tidbits like the amount of shade, the availability of water, the locations of toilets and whether neighbourhood dogs were friendly.

The landscape – with large farmhouses and borders of cypress trees – often seemed familiar, immortalised in countless paintings during the Renaissance by artists from the Sienese School.

Ten years ago, the Val d'Orcia, about 40 kilometres south of Siena, was named a UNESCO World Heritage site, chosen for its artistic influence, and its association with the utopian ideals of sustainable rural development.

Often we walked on dirt roads around vineyards or while watching a lone tractor traverse a wheat field. Some days we passed through the forest where unseen wild boar left hoof prints on muddy paths. We visited two monasteries and skirted one truffle reserve. Other travellers were few.

Most days we covered about 13km with an average elevation gain of 365 metres. We'd generally pass through the gates of the next walled town in the afternoon, just as the buses with the hordes of day-trippers from Siena and Florence were leaving.

That was ideal. Although the hill towns thrive on tourism, it was nice to move beyond the cheese, wine and souvenir shops and explore their historic fortifications (including spectacular views from the ramparts in Montalcino), small museums (like the mansion of the Piccolomini clan in Pienza) and beautiful churches.

We were fortunate to catch the start of the annual Festival of Barbarossa in San Quirico d'Orcia, held each June, in which the town's four quarters re-enact a 12th century competition with flag and archery contests.

Adding to the ambience in San Quirico was the discovery that our room at the hotel Palazzo del Capitano had a turret that afforded great sweeping views.

When booking the tour, we had a choice of three levels of hotels and opted for the middle, somewhere between standard and luxury. All of the hotels we stayed in were welcoming, clean and comfortable.

Our bags were always waiting in our room, giving us plenty of time to clean up and explore the town before choosing where to have that night's sumptuous dinner.

Being Tuscany, the food was fabulous, often featuring dishes made from local truffles, pecorino or cinghiale – wild boar.

Still, our most memorable meal was in the dining room at La Cisterna nel Borgo hotel, overlooking the well-preserved medieval piazza in the town of Rocca d'Orcia. It featured innovative dishes created from recipes and spices collected by the proprietors when they travel the world in the off-season.

For wine, there was no place like Montepulciano, where restaurants like La Bottega del Nobile boasted as many as 60 local offerings by the glass. The famous city is often associated with the Val d'Orcia and was a stop on our trip, even though it sits in a neighbouring territory.

And that bottle of Brunello? It was exquisite. But I was glad I had decided to carry only one, because it turned out that the winery shipped. So many months later, with a case in my basement, I'm still enjoying the fruits of my trip.

If You Go…

GIROSOLE: girosole.com. Tour company organises small group walking tours of Italy.

VAL D'ORCIA: whc.unesco.org/en/list/1026. UNESCO World Heritage site in Siena, in the Tuscany region of Italy. Walking itineraries: parcodellavaldorcia.com/en/itinerari.asp

PALAZZO DEL CAPITANO: palazzodelcapitano.com/en/index.html. Hotel located in San Quirico d'Orcia. Rates vary by room and date.