Tuscany is one of Italy’s most picturesque and visited regions, famous for its delicious wine and food and incredible artistic legacy. This eight-day tour is both off-the-beaten track and bespoke, organized by Exodus Travels, a company founded in 1974 which offers walking, cycling and cultural holidays. While Exodus sets up the itineraries and hotels and supplies the maps, guests can choose the timing and even adjust the distance of the walks, as well as what to do on off days.

My tour starts and ends in Volterra, a hilltop city founded by the Etruscans with a gate that dates back 2,500 years. The route alternates between forest paths and strade bianche (unsurfaced stone roads) as it passes through a series of stunning medieval hilltop towns, like San Gimignano, flanked by 14 towers built as symbols of status and wealth by noble families.

We are on our own, and yet not; always around the corner is the skilled, British-born Frankie.

While we walk the hills, Frankie, whose real name is Mark Franklin and who also works as a Tour de France bike mechanic, ferries our luggage between towns in his van. Should anything go wrong — an encounter with a venomous snake/wild boar/grumpy fellow walker — he is just a phone call away. This is adventure, minus the hassle, as he puts it.

For long stretches of time, we pass nobody, such as on day two, when we head from the village of Casole d’Elsa to Colle di Val d’Elsa, following the beautiful turquoise Elsa River, which forms part of the old pilgrim trail.

The walk provides an intimate glimpse into the timelessness of Tuscany’s culture and uniformity of style, from the geraniums in the earthenware pots placed on farmers’ window sills to the tidy tomato vines and majestic Cyprus trees that stand like sentries, marking borders, subdivisions and waypoints.

The temperature soars to 34 C, and I am grateful for my water bottle. My initial excitement gives way to a certain crabbiness as the sweat pours down my back and my idealized vision of skipping through sunflower fields yields to the reality of vigorous uphill climbs. I start to wonder when the 10-kilometre stroll will ever end.

As if on cue, we come up out of the river valley to the city road of Colle di Val d’Elsa. Hot but gratified, we walk up a hill to our hotel, located just outside the town: Relais della Rovere, a 12th-century Benedictine Abbey-cum-luxury hotel. It radiates a sense of meditative peace as only the former home of a Pope can (it once housed Cardinal Giuliano della Rovere before he was enthroned as Pope Julius II in 1503). There are remnants of frescoes on the walls, vaulted ceilings, ivy-covered pathways and manicured gardens.

I relax by the pool and take in the mesmerizing stillness of the hills, feeling a kind of tranquility I usually only experience after a long session of hot yoga and meditation. Later that evening, I dine on pasta with wild boar sauce, Caprese salad and a local Chianti in the candlelit courtyard.

Tuscan cuisine — Italy’s most revered — is based on cucina povera, or peasant cuisine, with a focus on natural ingredients, including locally-produced olive oil, salt-cured meats, pecorino (sheep’s cheese), wild mushrooms and fresh vegetables and fruits. Along the walking trails, signs warn us not to pick the porcini mushrooms; they are the property of locals. Shooting wild boar is also just for locals.

Part of the appeal of this trip is also its flexibility. When I ask to add on a visit to San Marino, which claims to be the world’s oldest surviving republic dating back to 301 AD, Exodus is happy to organize a driver to ferry me there (a three-and-a-half-hour drive away, it is, alas, too far to walk, even for an Exodus client). I cross the border from Italy into a distinct country of 33,000 people, which has been declared a UNESCO World Heritage site. San Marino boasts its own passport, flag, coins, constitution, bank and even university. I take a funicular up to the old section and walk the ramparts between three old fortresses with a tremendous view of the hills below.

On another off day, Frankie drops me just outside Florence, Tuscany’s capital and a Renaissance art mecca. I approach the city from the south, crossing the famous Ponte Vecchia across the Arno River, peering into tiny shops which, in accordance with a 1595 decree, sell only gold.

With a limited amount of time in Florence, I choose to see Donatello’s incredible bronze statue of a boy-like David in the Bargello Museum, the splendid striped marble Duomo, with its green, white and pink façade, and the Palazzo Pitti, once the seat of the Medici family. I have no time to visit the Uffizi, but touch the snout of the bronze porcellino or pig in the market and hope for the good fortune to make a return visit to this great city, which bustles with tourists exploring the palaces and galleries.