Puglia cycling tour review: Cycling the idyllic, sun-kissed heel of Italy's boot

It's noon on the first day of our Puglia cycling tour when we pedal into Otranto, one of the region's most historic port towns.

Pausing by a pretty clifftop chapel dedicated to the Virgin Mary, the warm, slightly breezy, salty sea air is alive with the sound of pealing bells and there, below us, under a cloudless sky, is the Adriatic, a blanket of navy blue with pockets of astonishingly clear azure water closer to the shore, sparkling under the midday sun, and seducing a cluster of tanned, scantily-clad bathers.

We'll get used to views like this on our five-day sojourn in Puglia – a remote, overwhelmingly rural slice of south-eastern Italy often referred to as "the heel of Italy's boot".

This isn't your bog-standard bike ride. We're doing things in style with Butterfield & Robinson, a luxury Toronto-based operator that blends pulse-raising, muscle-flexing adventures with memorable pit stops, where you meet engaging local characters and glean absorbing insights into the culture, heritage and (especially) cuisine.

Following the directions on the electronic tablet attached to our sleek Bianchi bicycles, we whizz down to Otranto's arching seafront promenade, past rocks speckled with sun-worshippers, and smart-casual couples ambling hand in hand, until the American-accented voice on our tablets tells us to park up beside I Villani D'Aragona – one of a smattering of laid-back alfresco cafes and restaurants within a pebble's throw of the waterfront.

For the next hour or so – it's almost impossible not to lose track of time – we're served mouth-watering dishes to share around our gazebo-shaded table: grilled squid and shrimp salad, plump tomatoes and mozzarella, risotto with asparagus, parsley and mountain mushrooms, eggplant and zucchini, pacchero (a tube-shaped pasta popular in southern Italy) coated in a ragu-like sauce.

It's all complemented by a selection of refreshing wines, including an excellent sparkling rose reared within riding distance of Otranto. Roberto, one of the three Italian B&R guides accompanying us, reveals everything is regionally-sourced, much of it organic. The Pugliese (people of Puglia), he says, are always proud to show off their cooking talents and bountiful fresh produce and almost take it as a personal insult if you don't tuck in. "The portions are usually huge," adds Roberto, "but at lunchtimes, they compress things for us so we can actually bike in the afternoons."

Nevertheless, I feel a few kilos heavier when I haul myself up and return to "Smooth Sailing" (everyone's bike has a moniker etched onto the frame). Pushing our wheels through the sloping, labyrinthine lanes of Otranto's tranquil walled old quarter, we pass a medieval cathedral known throughout Italy for its decorative mosaic floor, and an imposing fortress with a yawning moat and chunky cylindrical towers, built in the late 15th century by the Aragonese – one of myriad foreign powers to settle on Pugliese shores (everyone from ancient Greek sailors to Algerian pirates have called by).

These fortifications were commissioned after a brutal siege by the Turkish Ottomans in 1480, when hundreds of the town's residents were slaughtered.

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Leaving Otranto behind, we ride past crumbling 11th century Norman watchtowers, perched on steep clifftops, with the Adriatic shimmering about 100 metres below, lapping a necklace of limestone caves and pebbly and sandy coves, many only accessible by yacht, fishing boat or precipitous stairways.

The coastal scenery is almost Amalfi-esque in its drama and beauty, though, fortunately for us, traffic is much lighter. In fact, as we mostly dodge busy A-routes, and stick mainly to quieter country roads, we almost see as many cyclists and tractors as motorists on this trip. It helps that we're here in mid-September – outside the peak summer season. Temperatures are still balmy enough, though, in the mid-to-late 20s; almost perfect for cycling.

When we're not on saddles, we're almost invariably savouring delightful pit stops, such as Masseria Montelauro, where we bed down for the first two nights. A masseria is an old fortified farmhouse-cum-feudal village. Many in Puglia are now family-run hotels and B&Bs, tucked down secluded lanes, hedged by vegetable fields, orchards, vineyards and olive groves (it's estimated Puglia has 60 million olive trees – more olives and olive oil is produced here than any other Italian region – and it feels like we see a few million of these gnarled, silvery-leafed trees on our travels).

Among the more upmarket masserie, Montelauro has 29 rooms, with rustic-contemporary decor, in the whitewashed farmhouse and outbuildings. The French doors of my sweetly-scented hideaway (room 20) open out onto a tree-shaded lawn with a pool and cosy sofas and loungers. Spa treatments can be booked at this masseria and fine-dining devoured at the on-site restaurant.

We'll eat here tomorrow – and sample citrusy whites, ruby-hued roses and full-bodied reds during a wine-tasting session flaunting Puglia's diverse terroir – but for our first evening meal, we're transferred by coach to the neighbouring village of Casamassella. Welcoming us is Valentina, whose family own the fairy-tale 12th century castle looming over the village square.

After canapes and prosecco in the atmospheric, dimly-lit courtyard, and a tour of the castle's romantic garden and antique-adorned rooms, we feast, in the vaulted banquet room, on dishes like sesame-encrusted tuna with fresh vegetables and creamy desserts like panna cotta. Then we're treated to a performance by Ghetonia, a Pugliese folk band, whose lyrics are sung, with gusto, in Griko – an old Greek dialect spoken in a series of bilingual towns and villages in Salento, the southern chunk of Puglia. At one stage, a woman twirling a red scarf appears and beckons us all for a dance. Some – especially me, a truly appalling dancer – are more reticent than others. But everyone is in good spirits. The 19 in our group – couples, families, groups of friends, ranging from twentysomethings to septuagenarians; Americans, Canadians, Brazilians and Costa Ricans – get along swimmingly. Most have travelled with B&R before. Some are on their seventh trip.

It's easy to see why they come back for more. Most things on a B&R trip – location, food, drink, accommodation – are worth writing home, or Instagramming, about. Organisation is top-notch, and there's a good balance between exercise and indulgence. Every day, there's a regular ride (35-60 kilometres), or a longer jaunt (add another 20 kilometres or so). You choose – and cycle at your own pace, though your inner competitor may inspire you to surge ahead of the peloton.

On day two, I tackle the Century Ride – a 100-kilometre option that's a feature on B&R cycling trips. Retracing a previous stage of the Giro d'Italia – the Italian answer to the Tour de France – it snakes along the coast towards the town of Santa Maria di Leuca. Nestled where the Adriatic and Ionian seas meet, this is apparently where St Peter first landed in Italy to spread God's word. Beside a Catholic sanctuary – built over a ruined temple to the Roman god, Minerva – I glance out to sea, hoping to spy distant lands. I don't, but the Greek island of Corfu and Albania are a little over 100 kilometres away as the gull flies.

Like the Giro d'Italia competitors, we have great back-up, from our dedicated, good-natured guides Roberto, Marella and Marianna. One cycles; the other two drive support vans and sporadically ply us with water, snack bars, chocolate and fruit (they also help solve any issues, including replacing flat tyres, if necessary). This trip is rated as "recreational", two out of five in terms of difficulty. We're faced with the odd steep climb, and occasional strong headwind, but nothing too taxing (a few co-riders have electric bikes and an uphill boost at the press of a button). If you do struggle, simply hop in the van and your wheels are loaded onto the trailer. Most days are actually reasonably flat, with some exhilarating downhills, where your tablet's speedometer may clock 40-50km/h.

Our last day especially will linger in the memory. We spend much of it pedalling past the iconic trulli of Puglia – ancient pointy-roofed, conical-shaped stone huts dotted in and around Alberobello, the most postcard-perfect of all the towns and villages we take a cappuccino break in. Some trulli are still lived-in. Others have morphed into bars, cafes and gift stores. Later, before a lovely, lazy final afternoon at Masseria Torre Coccaro, a swanky beach-side resort, our group enjoys another delectable wine-fuelled lunch bursting with fresh, local produce (including mozzarella crafted in front of us by Angelo, a veteran Pugliese cheese-maker). As we eat, we share, well, cheesy puns about today's ride – and the trip as a whole. For most of us, it has been "trulli" wonderful.

Trip notes

Steve McKenna was a guest of Butterfield & Robinson

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traveller.com.au/italy

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TOUR

Butterfield & Robinson's guided Puglia Biking tour starts and finishes in the port cities of Brindisi and Bari. Priced from $US4495 and available between April and October, it includes four nights' accommodation in rural masserias, and one night at a hotel in the stunning Baroque city of Lecce. See butterfield.com

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