From Page to Port: Top Yachting Destinations Inspired by Literature

A good novel has the power to transport its reader thousands of miles away. But stepping (or sailing) into those literary worlds is easier than you think. Olivia Michel looks at wanderlust-inducing destinations from the classic novels in your library.

Valparaíso, Chile

In fiction: Chilean writer Isabel Allende begins Daughter of Fortune (1998) in the gritty yet romantic seaside town of Valparaíso. The protagonist Eliza grows up in a neighbourhood nestled between the city’s hills.

In reality: Lily Albin, owner of 37.5-metre sailing yacht Escapade, read Daughter of Fortune before sailing to Valparaíso in 2016. “The book’s description was quite accurate, so I wasn’t disappointed,” she says, recalling the colourful and cobbled streets. In particular, she was captivated by the vibrant shades of the artistic city and emphasises that “the house façades and murals are just wonderful”. For those whose curiosity has been piqued, Albin warns that “the Pacific Ocean on this coast is all very wild, so it would be for someone who is adventurous enough to go there”.

Writer’s retreat: Valparaíso’s labyrinthine stepped alleyways, effervescent culture and rolling hills have attracted artists for years. Albin recommends leaving the yacht in Puerto Deportivo and staying 10 minutes away, at the cherry-red Palacio Astoreca Hotel. Located on the central square, it features a lively jazz bar and an extensive art collection. Looking for a spot to become inspired? Take one of the city’s funicular railways to a hilltop look-out for a breathtaking vista over the metropolis.

Continue the story: Just to the north of Valparaíso, superyachts can stop by the coastal commune of Viña del Mar. The town may not have as much character as its more urban neighbour, but its glamorous resorts and lush, manicured gardens are well worth the trip.

Best by boat: Valparaíso’s centre is curved around a deep natural harbour, which historically served as the first port of call for sailors who had rounded Cape Horn. Yachts up to 100 metres can anchor there.

In fiction: Ian Fleming’s agent 007 is sent to the Bahamian capital in Thunderball (1961) for a high-stakes treasure hunt. Under the scorching sun, James Bond flies over South Bimini, battles villains in Grand Bahama and gambles at Nassau casino.

In reality: It’s apt that Fleming included a superyacht in Thunderball; SPECTRE’s Disco Volante would have fitted right in alongside Nassau’s many visitors, such as the 85-metre Solandge. Yachts are still encouraged to visit this winter as this area was not directly hit by Hurricane Dorian. An eclectic mix of Georgian houses, straw-roofed street stalls and high-rise hotels greets visitors in Downtown Nassau. Respite can be found at the golf course of New Providence’s Lyford Cay Club – Bond actor Sean Connery is even a member. Bordering the ocean, the gently sloping course is dotted with palms and vast water hazards, but guests will need a member’s written invitation in order to play. For food, head to Fish Fry, a street lined with painted stalls serving Bahamian beer and traditional fare, such as stuffed snapper or grilled grouper.

Avoid the clichés: The Bahamas is a favourite destination of Hendre du Plessis, captain of 49-metre charter yacht Remember When. “One of the biggest advantages is the close proximity to the US – you don’t have to travel halfway around the world to get to paradise,” he says. But Nassau can get busy during high season, so the captain recommends heading out to the Exumas chain, which “offers great shelter, short cruising to different locations, and some of the bluest, clearest, warmest water and the best beaches”.

Shaken, not stirred: If you’re heading to the Exumas, stop at the dressed-down beach bar of Staniel Cay Yacht Club for a rum punch. It’s right next door to the famous Pig Beach.

Best by boat: You’re never far from a marina in the Bahamas. Downtown Nassau has Bay Street Marina, which can take yachts up to 150 metres.

In fiction: In what has been hailed a modern classic, The Glass Palace (2000) tells the tale of the well-travelled Rajkumar. Readers follow his journey up the central artery of Myanmar, the Irrawaddy River, to reach the city of Mandalay. In the background of Rajkumar’s story, writer Amitav Ghosh reimagines the old land of Burma and its complex history.

In reality: The country is slowly opening up to tourists, but the rural regions remain similar to the world described by Ghosh. Backdropped by pagodas and paddy fields, the verdant, rolling countryside is traditional, undeveloped and unspoilt. The northern states (Kachin, Rakhine, Chin and Shan) still face upheaval, but charm and beauty can nonetheless be found in unaffected cities and on secluded beaches.

Rewrite the story: Rajkumar sailed through the Bay of Bengal to reach Myanmar. But Captain John Maas, of 51-metre Northern Sun, available for charter with Ocean Independence, clarifies that superyachts will only be able to access the scenic Mergui Archipelago, which lines the country’s southern coast. This is arguably the prettiest region, though. “The anchorages are deserted and the diving is untouched,” he says. “There are very few boats up there, but it is starting to be discovered by yachts.”

Happy ending: After exploring the Mergui, disembark in Yangon. This is the largest city in Myanmar, with markets and art galleries sprawling outward from the gilded temple at its centre.

Best by boat: Being relatively undiscovered, the archipelago has no established marinas. All boats entering the region must take a guide on board who will also advise on anchorages.

In fiction: The titular fisherman of The Old Man and the Sea (1952) begins his story setting out from Havana harbour to go fishing in the Florida Straits. After 84 days without a catch, the ageing Santiago hooks a giant marlin in the warm yet unforgiving waters.

In reality: It’s easy to see why Ernest Hemingway was seduced by Cuba. Despite its turbulent past, the crumbling, brightly coloured city of Havana has a bohemian allure. Driving down the Malecón Boulevard in a classic convertible is the best way to take in the colonial monuments and scenic beaches. But Havana is certainly not Cuba’s only attraction; the Jardines de la Reina coral reef off the country’s southern coast offers top-notch diving.

Havana nights: Rhythm and rum are two distinct features of Havana’s pulsating cultural centre: after sunset, salsa spots and mojitos are both easy to find. For a night on the town visit Fábrica de Arte Cubano, which serves as a modern art gallery by day and transforms into a club at night.

Plot twist: During Barack Obama’s US presidency, regulations were relaxed and exemptions were put in place that made it easier for American citizens and vessels to visit Cuba. Donald Trump has since clamped down, effectively making Cuba off limits for American visitors and yachts. “Cuba has been a fabulous yachting destination option for our American owners and charter guests,” Kathy Kennedy, COO of AvYachts, says. “We hope that in the future the regulatory environment will change and we will again be able to offer our owners and guests access to this unique destination.” However, it should be smoother sailing for foreign-flagged vessels.

Best by boat: Berth at the aptly named Marina Hemingway, which can take yachts of up to 70 metres and is a 20-minute drive from downtown Havana.

In fiction: Charles Nordhoff and James Norman Hall’s 1932 novel follows the final voyage of HMS Bounty in 1789. When the ship arrives in Tahiti’s Matavai Bay, the writers describe the crew being greeted by turquoise waves crashing at the feet of emerald mountains. The authors write of a paradise inhabited by locals as happy and hospitable as their surroundings.

In reality: Tahiti, the largest island in the Windward group of French Polynesia, epitomises a tropical haven, with romantic thatched-roof bungalows dotted along the shoreline and coconut vendors lining the streets. The exotic landscape and laid-back lifestyle make it easy to see why the rebellious lieutenant Fletcher Christian wanted to stay (so much that he incited a mutiny). Captain Claud Akers, of 32.9-metre motor yacht Askari, available for charter with Fraser, notes that the Bounty’s legacy can still be found ashore. He recommends hiking up to the palm-fringed Point Venus on Tahiti’s northern coast, where a monument still stands today.

Jump ship: Tahiti has some world-class dive sites. On the west coast, divers at the Aquarium site will spot angelfish swimming between the wrecks of schooners and a Cessna plane. Thrill-seekers should dive around Marado off Tahiti Iti (the smaller loop of the island’s figure-of-eight shape), which guarantees sightings of eels and blacktip sharks between the corals.

Sailor’s delight: With more than a hundred islands spread across a cruising ground roughly the same size as the Mediterranean, visiting yachts should head away from Tahiti to explore the rest of the archipelago. “One of my favourite islands, which also happens to be the closest island to Tahiti, is Mo’orea,” says Captain Akers. A swim with manta rays in Mo’orea’s stunning bays and lagoons is a standard feature of Askari itineraries.

Best by boat: Captain Akers says that, despite its untouched beauty, “Tahiti is well prepared for visiting yachts”. Yachts up to 100 metres can moor at Pape’ete Marina or, 10 minutes away, Marina Taina.