A romantic Italian road trip

Acurl of delicately scored squid, fat mussels on a bed of seabass ceviche, sprigs of salty samphire. The plates, sitting atop embroidered lace tablecloths, look like a work of art. Which is appropriate as the 100-days-only pop-up restaurant at Belmond Grand Hotel Timeo this summer pays tribute to German landscape painter Otto Geleng, who was so in love with Sicily. He was particularly beguiled by Taormina, a city conquered by everyone who passed through, which is littered with monuments to its dramatic past. The Greco-Roman amphitheatre rises up just behind the Belmond Grand Hotel Timeo and on the other side, under the bougainvillaea arches, is a terrace with views down to the waters of Naxos Bay and across to Mount Etna. Chef Roberto Toro is flexing his creative muscles in the most exquisite way. Supper here under the stars, at one of the eight tables, is a dreamy way to begin an Italian adventure.

For something a little more rustic, drive down to Mazzarò Bay, a deliciously old-fashioned pebbled beach with yellow and blue umbrellas. From the hotel Belmond Villa Sant’Andrea head out on a sailing trip to the sleepy island of Filicudi. The private boat stops off at local artists’ studios after a quick morning pitstop at the house of antiques dealer Nicola Rinaudo for homemade cakes and strong espressos. After exploring the island, lunch is a punchy bowl of spaghetti and caponata and crispy fritto misto made by Giuseppe Parella and his wife Zin Mar. The tour is an amazing way to get under the skin of this rugged, unspoilt Aeolian spot.

Sicily, though, is just the starting point. Fly from Catania up to Naples and pick up a classic Fiat 500, perfect for the windy route to the Amalfi Coast. Driving along the precipitous corniche roads on a clear day is dizzying: the heights, the views, the steep cliffs dropping into the inky Mediterranean. Wisteria- and ivy-clad Belmond Hotel Caruso in Ravello, a frescoed palazzo, sits like an eyrie 1,000ft above sea level.

Check availability for Belmond Hotel Caruso on Expedia now.

For a magical lunch, follow the donkeys through the winding streets of Scala, the oldest village on the Amalfi Coast, to the ancient Basilica of St Eustachio. Jackie Onassis loved to head up there when she stayed at the hotel in the early 1960s. Cushions and rugs are spread out among the crumbling 12th-century walls and columns – the most otherworldy setting for a picnic. The chef fills wicker baskets with local treats: sun-sweetened-tomato focaccia, creamy mozzarella, salami and omelettes, plus Caprese cake for pudding. Work it off by hiking down towards Amalfi afterwards. The route takes you through the cool, green Ferriere Valley with its waterfalls and pools, and past farmer Salvatore Aceto’s lemon harvest. If you’re lucky, he’ll offer a glass of ice-cold limoncello to anyone thirsty from the vertiginous walk.

After that hit of sea views, take a detour inland towards Florence. The five-hour drive motors past Rome and up through the stunning heart of Tuscany. The imposing Belmond Villa San Michele, which is in the Fiesole hills just outside of the city (but still with Duomo views), has glorious terraced gardens that draw visitors from around the world. At twilight, the smell of lavender, rosemary and lemon trees is softly enveloping, and the terraces become twinkly. Stiff Martinis are served in the newly opened Cloister Bar, and on the rickshaw-turned-stage street artists perform and bands play into the night.

Further into the Tuscan countryside, Belmond Castello di Casole is a brilliant base in which to really switch off and slow down. Take out the hotel’s bicycles to explore the further reaches of the estate, its cypress-tree-lined lanes, vineyards and olive groves. The energetic can pedal further, to the villages of Mensano, Radicondoli, Casole d’Elsa and Monteriggioni. The committed can do half-day journeys to San Gimignano and Colle di Val d’Elsa. And those looking for a rest can spend a long, lazy day by the swimming pool or in the terrifically good spa.

Onwards now, past Pisa, and up the coastal road, waving at Forte dei Marmi and La Spezia, to the glamorous fishing village of Portofino, and the impossibly lovely Belmond Hotel Splendido. The little port here is film-set pretty and charmingly atmospheric for early- evening drinks. But for something on a different level, the hotel can organise a cruise at dusk to the Abbey of San Fruttuoso, half an hour up the coast towards Camogli. This after-hours access to the remote Benedictine monastery, accessible only by boat or on foot, is magical. The cloisters are lit by candles and a private concert can be organised – a string quartet, a jazz band, even an Italian folk artist.

The final stop is the legendary Belmond Hotel Cipriani in Venice. The cross-country drive here can go through Parma, Modena and Bologna to tick off three of northern Italy’s top foodie hotspots, or up towards the foothills of Lombardy and glittering Lake Garda. Either way, finally crossing the lagoon on the Ponte della Libertà and seeing the Venice skyline appear is thrilling. Hand the car over in Piazzale Roma (or at Marco Polo airport) and take a private water taxi down the Giudecca canal to the classic brown-and-white-striped pontoon, unchanged in the hotel’s 60 years. This summer, the Cip’s Club chef Roberto Gatto is revealing his kitchen secrets. After a morning trip to the lively Rialto market, guests gather in the garden for a masterclass in picking herbs and vegetables before preparing lunch – tagliolini verdi or classic carpaccio – to eat under the pergola in the hotel’s vineyard.

The only way home from this majestic adventure has to be the Venice Simplon-Orient-Express. Check into one of the new Grand Suites: Istanbul, Venice and Paris (each decorated to reflect its city). They are supremely elegant, with deep-mattressed double beds, marble bathrooms, thick crystal-cut tumblers, chunky silver and doors that close with a satisfying clunk. Plus, of course, rich silks, intricate mosaics, bespoke glass lamps, carved fretwork and Champagne at the click of a finger, all the way back to London.

Belmond is a global collection of exceptional hotel and luxury travel adventures in some of the world’s most inspiring and enriching destinations. Discover more at belmond.com