The Highs & Lows Of Going On Holiday With Strangers When You're Single

Photographed by Anita Hero
As I judder towards my thirties like a landing plane, the idea of charging round European basement clubs alone with lust in my heart and Jägermeister on my halterneck becomes less and less appealing. The thought of turning up barefoot in an embassy and having to explain how I lost my passport and knickers at the same time, seems less funny somehow. Nobody is up for bed bugs, fake drugs, beer bongs and hostel verrucas anymore. The 35 degree hangovers have got punchier and the reality of eating jamon and bread for three meals a day is, frankly, digestively unviable.
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Of course I’d love to be a single girl with reservoirs of inner calm and holiday on my tod. I’d like to recline in a crisp cotton shirt, sip juniper gin and watch the sun set like one of those Vettriano paintings you get in dentist’s surgeries, but the thought of being alone with my thoughts makes my palms sweat. Not because my thoughts are necessarily self-destructive, but because they are profoundly dull.
I’m certainly pretentious enough to believe I would start penning my first poetry anthology, but realistically I’m not that deep and would probably use the free time to Facebook stalk primary school bullies, chew off my nails and write a tedious list of life admin to complete when I got home. More frightening still, I could become that woman who very performatively travels solo but spends 80% of the trip hitting on hotel staff and staging their radical self-acceptance #content sponsored by Per Una.
While my nipples aren’t as slippery as they used to be, there’s still life in the old girl yet. I’d be lying if I said I didn’t want a sprinkle of romantic intrigue. So, in pursuit of some sophisticated leisure time with a sexy twist, I hit Google for answers. What I found was a yacht charter company called Medsailors. It’s kind of like a flash 18-30s package holiday for millennials - a description my fingers actually just recoiled from as I typed.
I am, at heart, a basic bitch, so the heavily filtered, steel drum promo video of people looking tanned and cheerful had me at hello. Plus there were lots of close ups of bread and dips, two of my greatest passions. I chose the six day Greek ‘Saronic’ route for no better reason than I liked the word and spend my tax bill money on the £517 fee.
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At the port of Athens I was greeted by our alarmingly young skipper called Alistair. He had the unpredictable cheek flush of a 19-year-old with an oddly formal public-school-Dad personality. As we set sail, I was suddenly aware that I was boarding a floating prison on the waves.
I started to chill out a bit when I met the gang, a bunch of rosy 24-year-old school friends from Hull and a beautiful blogger from the US. They were a kind, clean, friendly, fresh-faced bunch. My American blogger bunkmate Taylor was considerably quieter and more surly than her ‘yaaaass kween’ digital presence. Despite my featuring heavily in her thirst content, IRL I could tell she had nothing but contempt for me. So, once we established she was still breastfeeding when "Wannabe" was released, I gave up trying to relate and slipped instantly into the role of jolly but out-of-touch aunt. On our first Island stop in Hydra, I went into kamikaze mode. I purchased a straw hat of the kind worn only by Japanese tourists and began asking annoying questions and saying "yoohoo" a lot like Hyacinth Bucket.
When sharing a pokey boat you find out fairly swiftly how much a stranger likes the music of Katy Perry, how easily they sleep, burn, puke and cry. On that first night we manufactured some common ground, when a 4am storm turned our boat into a vomitcano. You will also probably find out how smoothly your new friends’ turds flush. Over the coming days, a young man named Hugo would reveal himself to be both a gentleman and a peach in this domain.
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The trip is organised so that every morning you chug into a different beautiful secluded bay where you will find new people with Instagram bodies paddleboarding around to Dua Lipa while your knackered skipper and borderline slave, cooks you a slap up breakfast. At night you can eat with your boat, go out for drinks where there was always a designated tacky bar on every island if you’re in the mood for "Despacito" and chill.
Even if you hate punch parties and group fun, you would need to have a potato for a heart not to be moved by the beauty of the Greek islands which are just wall to whitewashed wall of vivid sunsets, leathery fishermen, bougainvillea and clip-cloppy horses. I spent my whole trip dipping my face and body alternately in tzatziki and crystal blue water. You can wake up every morning with a minor hangover and cure it without opening your eyes by launching yourself directly into the water like a felled tree.
Each boat in the convoy of eight had its own unique alchemy. There was a burnt stag do on the edge, a boat of travelling Australians who were all cheating on each other and I enjoyed catching fragments of tension from them all. I was aware that Hyacinth was probably beginning to get on her own crewmates' tits, so I found two equally immature media gals in their thirties on a neighbouring catamaran and became of stowaway of theirs.
We all fell quite predictably in love with Charlie the catamaran skipper, a Sylph-like, free love Sherpa cheeky Lost Boy, who intuitively tapped into our quarter-life crises. We drank and tanned irresponsibly all day. We talked sincerely about our star signs and our energies and, under his instruction, let the sunshine ‘kiss’ our armpits. We lay on the deck like three cackling rotisserie chickens and hopped on an off the islands getting overly attached to withered local cats and razzing around on quad bikes.
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At night we made bread on an open fire on the beach and consumed so much of the devil’s lettuce I actually dribbled. At one point I think I said the words, "the thing IS we're all just cogs in the capitalist machine".
The only mosquito in the ointment of that particular boat was a couple of 23-year-old Australian twins with quite staggeringly small dick energy, who we’ll call Toadfish and Rebecchi. They had intended to book a Malia lads holiday and their inability to judge the existing vibe was at first irritating, but ultimately heartbreaking. The boats all sit together at dinner where every night, the relentless sesh gremlins would buy two tankards of beer and shout "Let’s get fucked aaaahp!" to a table of frowns. During one soul-searching mezze session with cult leader Charlie, Toadfish tried to start a drinking chant that ended with him getting a kind, if patronising, lecture about sexual harassment.
One afternoon, wrapping up a two hour vegetarian banquet and DMC about the universe, tears of laughter streamed down our faces as Charlie shared stories from a goat farm in the Caribbean. “You have never seen anything more disgusting than a horny male goat," he said. "When they’re on heat their tongues come lolling out of their mouths and their eyes roll in their heads. When their pink willy lipstick comes out they give off this horrific smell…” I looked over his shoulder in the distance, Toadfish launching his second attempt at scrambling onto a paddleboard full of girls.
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While Toadfish was trying and failing to join the ‘Do Bits Society', I had inadvertently commissioned my own bits in the form of a hot, downy-blonde 24-year-old South African with salty Soltan lip from a neighbouring boat. Perhaps it was my eyes, bloodshot from Uzo and Marlborough reds, or my lectures on garden pruning and the patriarchy, but something was working. Despite the age gap, we found we had a lot in common. For example, we agreed that things were ‘cool’ and ‘good’ and the weather was ‘hot.’ This conversational minimalism worked very well for me, because after five days I was beginning to grow sick of the sound of my own voice. Instead, we spent the week going on long quiet walks and made the most of the whitewashed Grecian architecture by pressing each other up against it.
In any other mood I would have considered the last night of the holiday an actual Hellscape, flip flopping en masse up the cobbled streets in a toga made, Project Runway-style, from my own bedsheets. In theory it was a Dante’s inferno of embarrassment, but I felt none of it. I watched on fondly as sweet, sweet Hugo’s bedsheet loosened at the waist as he did the Macarena. In the corner, Taylor’s phone glowed as she frowned at her Instagram. Toadfish was slithering up behind a ra ra skirt with a boyfriend and Rebbechi was being waterboarded by his fourth pint in front of a baying crowd. Perhaps it was Guru Charlie’s influence, but I felt a sudden rush of relief and instant calm. Hyacinth and her naff hat were under no obligations. My heart filled with gratitude as I realised I was having the kind of reckless, chaotic group fun only 23-year-olds are supposed to have without having to actually be 23. Can't believe I'm saying it, but it's true what they say - youth really is wasted on the young.
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