Solo Drinking Is The Most Fun (& Most Frustrating) Thing About Travelling Alone

Photographed by Anna Jay
Recently, on a solo holiday to California, I met up with a friend for lunch, who wanted to know everything I’d been up to since I’d landed. After a highlights rundown that mostly included tacos, gelato and quite a lot of wine tasting, I told her about a brilliant little bar I’d stumbled across, where the Manhattans were so good I’d ended up staying for three.
"You went on your own? That’s amazing!" she said, with the same stunned admiration as if I’d just rowed solo across the Atlantic. I understood her reaction. As confident as I am with pretty much all aspects of solo travel, sitting alone at a bar still feels slightly out of my comfort zone — and it's the same for a lot of other women I know. We’ll board a plane to the other side of the globe on our own, navigate public transport in a foreign city and even sit in a restaurant by ourselves. But rock up solo to a bar? Now that’s gutsy.
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"I’d feel too self-conscious to enjoy it," one friend told me. "It's more hassle than it's worth," said another, who’d given it a shot but got sick of being pestered by men when she just wanted a quiet drink.
Why does a woman drinking alone still feel like such a big deal? After all, walk into pretty much any bar and you’ll see a solitary man hunched over a pint. Perhaps it has something to do with the fact that, in 2019, women who sit at bars alone are still being mistaken for prostitutes. Maybe because we’re constantly fed messages about how vulnerable we are. Or because we know from experience that a woman who dares to carve out her own space in the world — even if that’s just a spot at the bar — still draws scrutiny.

I sank mind-bending Martinis while the bartender filled me in on Keith Richards' favourite order (Campari with a side of liver and onions).

Here’s the thing, though. Taking yourself out for a drink — at home or abroad — is one of life’s greatest pleasures. Whether you want to meet people, silently people watch or quietly read a book with a cold glass of rosé, it's too much fun to leave to the men.
It took a long time for me to feel okay going to bars on my own while travelling. I’d happily spend all day exploring a strange city by myself, go for dinner alone, even to gigs solo. But if I fancied a drink, I’d go back to my hotel room and hit the mini bar, or crack open a bottle of supermarket wine in my apartment.
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But there were bars I wanted to go to, drinks I wanted to drink. So I started braving the odd solo afternoon beer. I’d have a nightcap or pre-dinner wine in hotel bars, where I realised there were loads of people happily drinking by themselves. Small steps.
Then, on a trip to New York, I met up with a friend — and seasoned solo drinker — who convinced me to throw myself in at the deep end. "Just do it," she said. "After the first drink it's fine." She was right. That night, I took myself out to a Brooklyn bar and ordered a glass of wine. I spent the first few sips feeling hideously awkward, pretending to read a book and constantly reaching for my phone. Two drinks in, I was chatting favourite boxsets with the bartender and having a ball.
Since then solo drinking has become as much a part of my travels as sightseeing. I’ve sunk $15 cocktails in fancy bars and €2 wine in pavement cafés, enjoyed cold beers in the blazing afternoon sun and ordered Old Fashioneds to see out the day.
Some drinking spots have been as memorable as any tourist attraction: Vienna’s 27-square-foot architectural wonder, Loos American Bar; Washington DC’s wood-panelled political watering hole, Off The Record; and LA’s glorious Musso & Frank Grill, a 100-year-old oasis of old school Hollywood charm, where I sank mind-bending Martinis while the bartender filled me in on Keith Richards' favourite order (Campari with a side of liver and onions).
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Then there was the time I ducked into a fancy New York hotel after an afternoon pounding the Soho streets to take the weight off my feet with a glass of wine. As I savoured each eye-wateringly expensive sip, a man dressed in beige chinos took the stool next to me, joining his friend for an afternoon whisky. His voice sounded familiar. Readers, it was James Bond. (Okay, it was Daniel Craig.)
Unfortunately, 007 didn’t strike up a conversation with me, but many others have. When you’re perched at the bar, people often want to talk. I’ve had conversations with strangers that lasted five minutes and one that stretched for five hours. I’ve had good chats and infuriating ones (Brexit, mainly). I’ve got recommendations for restaurants, galleries and local beauty spots I’d never find in a guide book.

I left one bar in LA when a seemingly polite man from Leeds started talking intensely about my calf muscles.

It’s all good. Until it isn’t. Because, inevitably, there are people — okay, men — who think a woman alone at a bar must be after more than just a decent drink. "Are you waiting for someone?" a fiftysomething man in a cowboy hat asked me on a recent trip. When I shook my head he took it as his cue to pull up a stool, compliment my dress and — an old favourite — tell me I should smile more. His friend was busy having a one-way conversation with another woman sat on her own who, despite keeping her eyes firmly glued to the pages of her book, hadn’t managed to get the message across. "Was he harassing you?" I asked her, after they’d finally left. "It’s fine, I’m used to it," she said.
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It sparked another conversation about how frustrating it can be trying to have a drink on your own as a woman. The assumptions. The pestering. Oh god, the pity. "I always think a book will help, but it weirdly seems to encourage guys to start a conversation," said my fellow solo drinker.
Even chats that start off innocent can take a turn for the worse. I left one bar in LA when a seemingly polite man from Leeds started talking intensely about my calf muscles.
It's moments like this which mean I still have to steel myself a bit every time I go out for a drink alone. It’s also why I prefer to perch at the bar, rather than a table. Bartenders have a pretty good instinct for if you want to chat or be left alone, and the good ones clock when someone is bothering you. I take props — a book, newspaper or magazine to read — but more often than not, I just sit there. People watching. Eavesdropping. Thinking. Drinking. And trying really hard not to look at my phone.
I’m careful about where and when I go. I don’t hit up city centre pubs at 10pm on a Saturday night. Restaurant and hotel bars are usually more sedate, and a good option if you’re dipping your solo drinking toes in. And if a bar has something on, like live music or comedy, it can give you more of a purpose to be there.
Really though, if you fancy a drink, you should just have one. Whenever and wherever you want to. People might talk to you. They may stare. After all, us lone female drinkers are still a rare beast. Ignore them. Order the good wine. Enjoy every sip. And if I see you there, the next one’s on me. Unless, of course, you just want to be left in peace.
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