Grand Traverse Classic - North to South

From Cinque Terre to the heel of Italy

The trip begins where the Ligurian coast crumples into the sea — Cinque Terre, the cluster of fishing villages clamped to cliffs above the Tyrrhenian. From there the route runs the entire spine of the country south, through Tuscany, Umbria, the high Apennines, Puglia, and on to the very tip of the Italian heel, where the Strait of Otranto separates the mainland from Albania. Seventeen days. Nearly 1,100 miles. Over 21,000 metres of climbing. It is the kind of trip that asks something of you, and the kind that rewards you for it.

At heart it is a long ride down the backbone of one country, through ten UNESCO sites and five national parks, on roads that the operator has spent years piecing together.

The terrain in three parts

The first stretch heads inland from the coast through the southern Tuscan Apennines, a stone landscape best known for the Carrara marble quarries — pale scars on the mountainsides that you can see from miles away. From Lucca, the route turns south through Chianti, then onto the rolling clay-and-chalk country of the Crete Senesi and the Val d'Orcia. This is the postcard-Tuscany section: hill towns, cypresses, the historic centre of Siena. Pretty, occasionally busy, lovely nonetheless.

The middle part is where it changes. Through Umbria the road climbs into Apennine villages perched on limestone, then on into Abruzzo and Molise — genuinely off-the-map territory for most British travellers. The route crosses the Gran Sasso, Majella and Matese national parks, riding through landscapes that don't tend to make it onto the Italian shortlist. Few visitors, unvarnished villages, real character.

Then the descent towards the Adriatic and into Puglia. Sunflower fields in summer, baroque town centres, Castel del Monte sitting alone on its hill, the Sassi of Matera, the trulli of Alberobello. The final days follow the coast down the heel to Otranto, the water turning clearer the further south you go.

Booking, fitness and what's involved

Saddle Skedaddle prices the trip from £4,195 per person across seventeen days. It is a guided road cycling holiday, so you'll be riding with a group and a support vehicle rather than navigating alone — and the camaraderie of that group is part of what past riders tend to mention most. One previous customer, Nigel from Hampshire, called it the trip to do if you were only going to do one of Skedaddle's.

A word on fitness: this is not a casual week. Twenty-one thousand metres of climbing across seventeen days averages to over 1,200 a day, with several proper Apennine passes thrown in. You'll want a decent base of miles in your legs and to be comfortable on long, hilly days back-to-back. For confident club riders looking to do something substantial in Italy — rather than ticking off Tuscany alone — it is the kind of route that justifies the time off work.

Departure dates, the trip notes document and the full inclusions list are available directly from Saddle Skedaddle.