Going to a bar alone isn't weird. You just need to know where to sit.
I've walked into wine bars in Sydney, cocktail bars in Rome and hotel bars in cities where I didn't know a single person. And after years of flying and travelling solo, I've learned that some of the best travel experiences start with simply sitting down for a drink.
But I remember when it wasn't quite so easy.
The San Francisco night that changed how I travel
The first time I went to San Francisco, someone warned me to stay away from a particular street and be careful because the area was dangerous.
Well, that was encouraging.
I was suddenly too nervous to go anywhere, so I went downstairs to the hotel bar, thinking I'd probably spend my entire trip hiding in my room.
Then I met a lady from Melbourne who happened to be sitting next to me.
We got chatting, and she started telling me about all the wonderful places to visit along Polk Street and down towards Fisherman's Wharf.
And just like that, my trip changed.
The next day, I ventured out. I found a wonderful old diner by the water, visited The Buena Vista Cafe for its famous Irish coffee, caught the cable car and wandered along the waterfront to the markets.
I wouldn't have done any of it if I hadn't met that woman at the bar.
The Buena Vista Cafe, opposite the cable car terminus at Fisherman's Wharf, is famous for its Irish coffee. It's one of those San Francisco institutions that's worth experiencing for yourself.
I can't remember the name of the breakfast diner I visited, but I remember the experience.
You just don't know who you're going to meet, or where one conversation might take you.
Sit at the bar. It's your friend.
If you're nervous about going to a bar alone, my advice is simple: look for a seat at the bar.
You're part of the room. You can watch the bartender, see what's being poured, ask questions and chat if you feel like it.
And if you don't? That's fine too.
Some evenings I want conversation. Other evenings I want a glass of wine and a little peace.
You don't need to pretend you're waiting for someone, bring a book or spend the entire evening looking at your phone.
You're there because you wanted a drink. That's enough.
Start early and keep it simple
If you're trying this for the first time, go around 5pm or 6pm, when many wine bars and neighbourhood bars are a little quieter.
Choose somewhere with comfortable bar seating. Order a glass of wine or something you enjoy. Ask the bartender for a recommendation if you're unsure.
You don't have to stay for hours. Have one drink, enjoy the atmosphere and leave whenever you like.
When I choose somewhere, I'm looking for welcoming staff, somewhere comfortable to sit, good drinks and an atmosphere where one person feels perfectly at home.
It's also why I ask other crew where they go when travelling. We spend so much time arriving in unfamiliar cities that we've learned the value of a good recommendation.
What about safety?
Trust your instincts.
Choose somewhere you feel comfortable, keep an eye on your drink and surroundings, and have a plan for getting back to your accommodation.
You never have to stay somewhere that doesn't feel right, and you never owe anyone a conversation.
Confidence isn't about ignoring your instincts. It's about trusting them.
Where to go in Sydney
From Surry Hills to Newtown, Enmore and Marrickville, Sydney has plenty of neighbourhood bars where you can settle in for a drink on your own.
If you're ready to give it a go, I've put together my guide to the Best solo bars in Sydney, with places to enjoy a drink without needing to organise a group or wait for someone else to be free.
Because sometimes the best thing about travelling alone is the person you haven't met yet.
You might find a new favourite bar.
You might discover a neighbourhood you never knew existed.
Or you might meet a lady from Melbourne who changes your entire trip.
You don't need to wait for someone else to be free. Just go.
See the Solo Sips and Bites Venue List for Sydney where you will find lots of solo friendly venues to try. Also check out the flight trails where you can download our free Sydney Wine Trails.