Why Your Next Holiday Should Be By Yourself

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Why Your Next Holiday Should Be By Yourself

Words by Mr Simon Usborne

22 August 2018

The dos and don’ts of travelling solo – according to the experts.

The dream of solo travel – the independence, the open road, the Moleskine journal in which you’ll sketch and write poetry – can differ from the reality of unsatisfactory solitude on park benches and tables for one in jam-packed restaurants. At its worst, solo travel can be, well, lonely, and confidence sapping. But in this era of the Insta-powered individual, there has never been a better time to strike out alone. In some cities, more than a quarter of Airbnb’s bookings are now made by solo travellers, while a global Visa survey in 2015 revealed that one in four of us travelled alone on our most recent trip, up from one in seven only two years earlier.

While the travel industry adapts, technology is making it easier to stay safe and to connect with like-minded people. And the stigma of solo travel is becoming a thing of the past. Solos, a specialist operator founded almost 40 years, told me recently that it used to post its brochures in opaque envelopes to avoid embarrassing its customers. Today, solo travel has become a lifestyle choice, a statement of independence.

There are ways – and apps – to ease the path of the social adventurer, and it is good to take the advice of seasoned soloists. People such as Mr Jeremy Jauncey, a member of the MR PORTER Style CouncilInstagram travel pin-up and founder and CEO of @beautifuldestinations, an aspirational photography feed with more than 11 million followers. Mr Jauncey, who travels alone at least one week per month, uses Instagram for more than photo sharing. Before he travels, he’ll click on his destination’s geotag and related tags for restaurants, hotels or bars. “I’ve discovered hidden beaches in the Philippines and amazing family-owned restaurants in Jordan that aren’t picked up by the travel review sites,” he says.

He does the same when he wants to meet people, by sliding into the DMs of users whose photos he likes and asking for recommendations. “I did this during the World Cup and ended up watching the England-Colombia game with a street full of die-hard fans in Cartagena,” he says. Taking this route is fraught with the risk of perceived sleaze, of course. Mr Jauncey recommends playing it cool and romance-neutral so that a recipient is flattered by the interest in their local knowledge rather than more tangible assets.

Specific apps for sociable solo travellers have mushroomed. Localeur uses locals in more than 80 cities to recommend restaurants, cafés and hotels. Cool Cousin goes deeper, allowing users to message locals and follow their guides to destinations as diverse as Stockholm and Buenos Aires. SoloTraveller combines local recommendations with a social network for comparing experiences and meeting up. Mr Troy Elmes, the app’s Australian founder, came up with the idea while walking the Camino de Santiago in Spain. “There was an incredibly large and diverse group of travellers all looking for a connection,” he says. He also recommends investing in a Skype premium account for affordable calls and buying a local Sim card on arrival.

Other apps focus on food and the dreaded table for one. Mr Lee Thompson, a former photojournalist and co-founder of Flash Pack, a holiday company for solo travellers in their thirties and forties, swears by EatWith, a peer-to-peer dining site with hosts and supper clubs in hundreds of cities. “I travel to India a lot and recently signed up to an evening in Delhi with the Secret Supper Club,” he says. “I spent the night with a group of 12 locals over cocktails and drank with them until the early hours at a bar I’d never have discovered by myself.”

Beyond the potential of technology to satisfy our social instincts, a table for one can be a joy. When I was last in Hong Kong, I flew solo a couple of times. At Ho Lee Fook, a casually hip fusion joint that was already overflowing at 6.00pm, I spotted a non-table stranded beyond the main dining room and convinced the maître d’ that it was big enough for me. “Make sure you dress well and walk in with plenty of confidence,” advises Mr Thompson.

If nabbing a table for one can be hard, booking a hotel room without hearing the two words that are the scourge of the solo traveler – single supplement – can be a challenge. Hotels still price rooms as doubles and single rooms are rare. “One way around it is to get on the phone and speak to someone on the front desk,” says Mr Thompson. “So many people book via third-party websites that if you go the old-school route, it can make a real difference.” Sweet-talking is more likely to pay off last minute and/or off season when hotels become desperate to sell their rooms. “Just be friendly, direct and explain your situation,” says Mr Thompson. “You’ll be amazed how far it can get you.” Some cruise lines are waking up to their rising popularity among solo travellers, meanwhile, by cancelling supplements during promotional periods and building dozens of desirable single cabins in new and refurbished ships. Hotels may wish to follow their lead.

Social and fitness activities have boomed for solo travellers who are not content to stroll between galleries and restaurants with a book in hand. Ms Jenny Graham, managing director of Quintessentially Travel, recommends Go! Running Tours, which connects curious joggers with local tour guides. “I always like to hunt out local exercise classes,” she says. She has also made friends during boxing classes in New York, paddle boarding sessions in San Francisco and a meditation class in Kyoto. She got over a breakup recently at The Body Camp, a luxury fitness retreat in Ibiza that keeps single supplements to a minimum.

Adventure travel companies are also attracting a growing number of solo travellers. Rapha Travel takes cyclists, many of them solo, on a growing number of its organised trips, while Roped Up connects skiers and snowboarders who want to share a mountain guide or instructor.

Safety can be a concern for solo travellers. There are several apps for that. TripWhistle Global has a call button that automatically goes through to the emergency number in dozens of countries and then shows you your precise location. RedZone pools government and news sources to tag potential high-risk areas and allows users to flag issues, while ICE Contact (In Case of Emergency) lets you display vital personal information such as blood type and emergency contact details on your phone’s lock screen should a kindly soul find you indisposed.

The Spot Gen3 device leads the field in GPS trackers for adventurers. It broadcasts your location to family or friends as often as every 150 seconds and has an SOS button for contacting local emergency services and a “check-in” button that sends a pre-written text or email to contacts even if you have no phone reception. Strava, meanwhile, the popular fitness tracking app, has launched a safety pack, which shares your location with friends when you go for a run or ride. Garmin’s LiveTrack offers a similar service for users of its Connect fitness app and devices.

Then there are the physical safeguards any traveller should consider, but which are particularly important when you’re alone. Travel with photocopies of your passport (and keep them apart from your passport) to make it easier to get a replacement if the worst happens. Always have your travel insurance policy handy, with the number to call in case of mishap. (No travel insurance? You’re mad.) Keep a second credit card in your hotel room safe. “I always have two wallets with me,” says Mr David Millar, the former pro cyclist, writer and high-end cycle clothier behind CHPT3, who regularly travels alone between races or on business. “One is a cardholder type for socialising and then I have a full wallet for travelling. I keep them separate so I always have an escape plan if some thieving bastard nicks one, or I get drunk and drop it getting out a taxi.”

Done right and with the means and tech to provide just the right level of social interaction, including none at all, solo travel can be an enriching voyage of self-discovery and permissible selfishness. “It’s one of those rare moments in life when we can go off-grid,” says Mr Millar. “Nobody expects to be in touch with you when you’re on the move, and in the modern world that is a precious thing.”

Holiday essentials

Illustrations by Mr Kouzou Sakai