From Robert Louis Stevenson’s love of simple journeying to the evolving, and often misunderstood, world of modern private aviation, Camilla Frances travels to Monaco to experience a different kind of member-led travel – one that challenges assumptions of excess and values skilled craftsmanship even at 40,000 feet.

Sydney-based Australian interior designer Tamsin Johnson shares her favorite spots in the New South Wales capital, which enjoys an enviable balance of beach and buzz. Vast stretches of coastline, excellent restaurants and a well-established art and design scene make Sydney a great place to live, work and visit. Read on for Tamsin's insider guide.

The Orient Express has been transporting passengers in style for well over a century, but until a year ago never had a dedicated all-Italian train. Now, with multiple journeys across Italy, a hotel in Rome and an imminent opening in Venice, the fabled brand – as much a cultural symbol as a train – is racing towards its future. Camilla Frances hops on board to experience one of La Dolce Vita's three-day Italian itineraries.

“Sometimes I think we only half live over here. The Italians live all the way,” wrote Ernest Hemingway to his sister in 1919. The writer spent long seasons at The Gritti Palace, the Gothic palazzo on the Grand Canal that has housed the city's most devoted admirers for over a century. Sophie Goodwin checks-in to the Hemingway Presidential Suite and discovers the unbridled glory of Venice.

Writer and photographer Chris Wallace journeys to Chile's extremes, from the country's mystical volcanoes and temperate rainforests, to the otherworldly landscapes of the Atacama desert. Join Chris as he discovers a land of striking and surreal beauty.

Photographer Sam Parkes has spent 13 summers on a hill farm on the north-west shores of Loch Lomond, joining farmers and their dogs to gather wild hill sheep from vast Highland slopes. Walking miles of rough ground, he reflects on the drama of the gather, the shared meals, the sense of communal purpose and the inexorable pull of the Scottish landscape.

Beyond India’s well-trodden golden triangle, the number of visitors to Bikaner – on the edge of the vast Thar Desert in Northern Rajasthan – is comparatively small, often considered a stopover en route to Rajasthan’s more famous towns. Those who make the journey, and stay a little longer, are rewarded with crowd-free sights and a town not obviously touched by tourism.

Between Gabon and the equator lies São Tomé & Principe, a small island state where 16th-century forts and tiled villas – remnants of its colonial past – stand crumbling and untouched by tourism. This makes the island's capital feel like a time capsule of Atlantic trade and plantation wealth, amid jungle cliffs and black-sand beaches, finds Harrison Thane.

Villa Santa Anna claimed Erica Firpo from the moment she walked inside and sat down on the salotto’s soft leather couches. The beautiful private house is one of 11 properties (and 42 suites) on the 2000-hectare Tuscan estate managed by Castiglion del Bosco, A Rosewood Hotel.

Escaping the whirl of the Pink City – but not before checking-in to two of its stylish new stays – Kate Lough explores a slower side of Rajasthan. From organic living on sustainable farms overlooking the Aravali Hills to tiger spotting in tented safari lodges close to Ranthambore Park, she settles into the gentler ways of rural Rajasthani life.

"If you want to discover an East European city, which is still a little under-the-radar, I highly recommend a stop in Plovdiv," says photographer Joanna Maclennan who's long been captivated by Bulgaria's rich cultural history and photogenic painted houses. She shares beautiful images and a tips-filled postcard from Plovdiv.

Mary Randolph Carter – author, photographer, collector, former Creative Director of Ralph Lauren and self-titled 'junker' – shares her favorite flea markets in the US, from a legendary weekend pop-up on the East Coast and an iconic flea on the West Coast, to a vintage-hunter’s dream in a country field. She also shares the ‘Golden Rules’ of vintage hunting once shared with her by a notable dealer.

Although it ought to be forbidden to use the word odyssey when writing about Greece, certain journeys do seem to resist any other term, finds writer and photographer Sam Parkes. He travels to Mani for "a pilgrimage of sorts", on the trail of Patrick Leigh Fermor, who first visited the Southern Greek peninsula in the 1950s while, researching his book Mani: Travels in the Southern Peloponnese.

As city-centre hotels vie for ways to stand out from their competitors, few could compete with the magic of a hotel set inside the enchanting Copenhagen amusement park, Tivoli, that once inspired Walt Disney. If it seems absurd to imagine that a five-star hotel inside an amusement park could be genuinely serene, think again, writes Eleanor Cording-Booth.

With the northern hemisphere feeling distinctly frosty, our minds are wandering to warmer climes, winter sun and thoughts of New Year travel. Photographer Joanna Maclennan makes a strong case for the inexorable pull of Fès, sharing a tips-filled postcard and set of arresting images from the mystical Moroccan city.

In the Alentejo, craft and life cohabit with poise. Sarah Siese explores the region and finds that São Lourenço do Barrocal, a remote 2,000-acre estate in the foothills of Monsaraz, is both a refuge and a revelation that contemporary luxury may, after all, be founded on radical simplicity.