Hike the photogenic coastal trails and serene rural byways of Saga and Nagasaki and you’ll be walking in epic footsteps. The cosmopolitan eastern prefectures, for centuries Japan’s only gateway to the wider world, hosted Chinese and Dutch merchants, Korean potters and Portuguese missionaries, along with English fortune seekers pursuing the patronage of samurai warlords.

The guided nine-night route reveals glorious scenery and amazing life stories. The birthplace of revered Ming dynasty general Zheng Chenggong, Nagasaki is also the adopted home and burial ground of William Adams, who inspired the novel Shogun. Saga’s clear East China Sea, meanwhile, is where legendary free-diver Jacques Mayol, immortalised in Luc Besson’s The Big Blue, learned to swim and dive. Linking Fukuoka with Kumamoto, the journey embraces historic maritime hubs including Karatsu, Hirado and vibrant Nagasaki; the once-secret village that crafted Japan’s exquisite porcelain; and the celebrated hot springs of Ureshino and Unzen.

Saga and Nagasaki: Cultural Crossroads from £3,175pp excl flights; walkjapan.com

Goggles secure? Swim cap tight? Mind focused? Perfect. You’re about to swim from Europe to Asia: a five-kilometre plunge through muscular currents, lauded as one of the world’s most memorable open-water events for its intoxicating blend of history, romance and endurance. Held every 30 August on Turkey’s Victory Day, commemorating its 1922 defeat of Greek invaders, the swim sees the Hellespont (also known as the Dardanelles or Çanakkalestrait) and its frenetically busy shipping lane closed for several hours, allowing up to 2,000 people to tackle the choppy waters.

Dubbed “the world’s oldest swim”, it’s the stuff of legend. Quite literally. In Greek mythology, Leander conquered the Strait of Çanakkale on a nightly basis, guided through the coal-dark sea by the lamp of his lover Hero, a priestess of Aphrodite – poetic inspiration for Lord Byron’s successful crossing in 1810: the foundation of the modern event.

Hellespont Europe to Asia from £1,190pp incl booking through SwimTrek, three nights B&B accommodation, transfers, acclimatisation swim and boat tour; swimtrek.com

Prepare for a heavenly experience and pray the weather gods are smiling. On 10 August, you’ll sail across southwest Iceland’s vast Faxaflói Bay: mountain-ringed home of whales, dolphins and porpoises. Your eyes, however, will devour sky, not ocean. You’ll be looking up (wearing geeky protective glasses) as the imposter moon eclipses the sun, plunging the world into otherworldly half-light.

Astral theatrics aside, this four-day adventure lets you soak in the Blue Lagoon’s thermal waters, explore Reykjanes Peninsula and chase the Golden Circle linking Unesco-listed Thingvellir National Park’s craggy gorges with the thunderous Gullfoss waterfall, as well as Geysir, where you’ll savour hot-spring-baked bread with eggs and herring. For a splash of urban cool, hit Reykjavík’s cosy cafés, gourmet restaurants and concrete cathedral, its Expressionist design inspired by Iceland’s basalt lava columns: the perfect spot to pray for clear Faxaflói Bay skies on 10 August.

Reykjavík and Solar Eclipse Adventure from £1,299pp incl accommodation, some meals, transfers and tours; discover-the-world.com

Vespas: stylish, fun and iconic with a Gregory Peck, Audrey Hepburn, Roman Holiday vibe. Now translate the dolce vita to verdant Southeast Asia and you’ve got one of the meticulously crafted, bespoke journeys created to celebrate travel company Tropical Sky’s 20th anniversary. After decompressing in Hanoi’s opulent Capella hotel, plunge into the capital’s culinary soul on a Vespa street food tour before switching to alternative heritage transport for a two-day cruise over Bai Tu Long Bay’s emerald waters past jagged limestone karsts, mist-shrouded cliffs and floating fishing villages.

Back on two vintage wheels, explore the serene rice paddies and meandering rivers that swaddle historic Hoi An, then fly to Siem Reap for a private sunrise Vespa tour around Angkor Wat’s mesmerising 12th-century Khmer temples. “Cambodian Holiday” might not have quite the same ring, but it’s still a cinematic finale to an extraordinary trip.

Asian Discovery Vespa Road Trip from £8,150pp incl business-class flights, meals, transfers and tour; tropicalsky.co.uk

High-octane thrills and high luxury sync perfectly on this wide-ranging bespoke expedition into a stellar Arabian landscape. Acclimatise in the palatial Chedi Muscat before driving into the awe-inspiring Al Hajar peaks, where you’ll mountain bike among fluttering butterflies and source ingredients for an Omani feast alongside a top chef in the historic Nizwa Souk.

Staying in the spectacular Alila Jabal Akhdar, modelled on an ancient fort, overlooking Wadi Ghul – “Arabia’s Grand Canyon” – tackle a heart-in-mouth slice of the via ferrata at Jebel Shams, Oman’s highest summit, and study star-drenched skies with an expert astronomer. Keep pulse rates up with a 4×4 drive into the desert to microlight over sweeping Wahiba Sands, before reaching the Empty Quarter to sleep in uber-comfortable Bedouin tents, riding camels out to dune-top sundowners. Finish by paragliding, 007-style, down onto Six Senses Zighy Bay beach to swim with turtles and sharks. Mission accomplished.

Ultimate Desert Adventure in Oman from £22,800pp, excl flights; pelorustravel.com

Don your Kilgour tailored tux or black velvet gown and prepare for the world’s most glamorous murder mystery case. Bespoke immersive experiences hit differently when you charter a private superyacht for a suspense-laden thriller, with every guest given a role, be it a classic 1930s whodunnit, contemporary psychological drama or double-crossing spy. You charter the yacht, choose the location, order the intrigue.

Whatever the case, one piece of evidence is stone-cold fact: the Christina O is the ultimate stage for your holiday crime scene. Once owned by tycoon Aristotle Onassis, the yacht has hosted everyone from Hollywood royalty including Marilyn Monroe and Grace Kelly, to political A-listers: Churchill first met JFK in Ari’s Bar – the perfect spot for whispered clues or covert encounters. So, whether it’s a murder in Norway’s fjords, political assassination in the Caribbean or diamond theft on the French Riviera, let the mystery commence.

Murder Mystery yacht experience on the Christina O from around £607,000 per week; pelorusyachting.com

It’s gym life, but not as we know it – and an opportunity to experience the private island retreat of royalty, rock stars and discrete billionaires with its laid-back but celebrated social life. The week-long boutique wellness festivals include multiple healthy activities from sunrise coastal hikes and sunset breathwork, snorkelling with turtles and cardio-tennis on Macaroni Beach, to ocean-view yoga at Lagoon Bay, studio-based pilates and a Bamford spa treatment, alongside beach workouts, dance classes and kayaking.

You’ll also have the chance to sea-swim with horses, scuba dive and join personal training sessions. But the week’s wellness is about more than health-focused activities. Far more. It also highlights Mustique’s fun, eccentric character with a beach party, Cotton House cocktails and jazz and dancing at legendary Basil’s Bar.

Health and Happiness on Mustique Island, 14-21 May and 11-18 June, from £5,790pp incl transfer flights from St Lucia and Barbados, luxury villa accommodation, all meals and activities; thehealthyholidaycompany.co.uk

China’s Gouli Valleys do exactly what it says on the tin. An interconnecting web of five valleys on the eastern edge of the Tibetan Plateau, the remote area is dubbed the Valley of the Cats for its generous populations of three famous Asian felines: snow leopard, Eurasian Lynx and Pallas’s cat. Until recently, access to the pristine secluded Qinghai province wilderness was challenging but as the region opens up, its wildlife treasures are slowly being discovered.

On this new small-group trip, intrepid travellers enter Gouli on foot or four-wheel drive alongside ecologist Terry Goble, scanning the slopes and ridgelines for evidence of the elusive creatures. You will also be watching for Tibetan fox and gazelle, woolly hare and blue sheep, as well as magnificent birdlife – from golden eagles and bearded vultures to Himalayan snowcock. In short, the little-visited region is an Attenborough documentary made real.

China’s Valley of the Cats from £5,495pp incl 12 nights’ accommodation, most meals, transfers, guiding and return flight; wildlifeworldwide.com