01 June 2019
Plane wing

I recently took a trip to the literal unknown. I packed my bags and I headed for Stansted Airport with my passport in hand, but I did not know where I was going.

See, I’d vowed that for one year, I would try to live my life as an extrovert. I vowed to do things that scared me – and travelling to the unknown, with zero preparation of my own was on the list. For around £200, you can book a flight and accommodation with a company called Srprs.Me. They choose your destination for you, and they reveal it to you just before you get to the airport. All you have to do is ‘prepare for ceaseless adventure’.

Find a quiet spot.

Sure. Easy. Fun, you say. Except I’m a shy introvert, so while I don’t mind spending time by myself, I’m not built for travelling solo, because I struggle to make quick and easy connections with people and I get overwhelmed by large crowds.

On this trip, I’m in search of a feeling: that magical sense that you can’t possibly predict what’s going to happen next or who you are going to meet or where they are going to take you. In this state, everything flows, every surprise is a delight, and new people guide you to special adventures. My friend Hannah calls this ‘la-la land’. Sometimes you can fall into la-la land (not the musical) on your doorstep, but we all know it’s easier to find that feeling of infinite possibility when you are in a foreign land.

Here is what I learned about travelling alone:

1. Pick your location carefully and embrace ‘shoulder season’

While I put my fate in the hands of the travel gods, I did learn that location can be the most important factor on a solo trip. If, like me, you loathe large crowds, try to avoid peak tourist season… don’t book Rome in the middle of summer. Learn to love ‘shoulder season’ aka spring or early autumn for better deals and fewer people. Always research this – it could make or break your holiday, transforming a peaceful beach break into a crowded free-for-all.

2. Find the quiet spots in busy areas

Even if you do end up in Rome during peak season, make a point of wandering down the quieter streets. It’s always so wonderful to see what real life somewhere else actually looks like. Talking to locals or people watching is a sure fire way to get a feel for the place you’re in and to make the most of it.

3. Take small group tours

Introverts aren’t necessarily built for solo travel, it can just be overwhelming to take in so many new things at once. I’ve found that by taking small cooking classes or short group tours, you can meet new people in a friendly, low-key environment, but if they tire you out, you’re usually done in a few hours so you can escape for vital alone time. Last summer, I took an amazing boat trip with about 15 strangers and it was really fun to share in the gorgeous views, the snorkeling and the hidden beaches. Then I waved them goodbye and ate a delicious meal alone by the sea. 

4. Pack a book and headphones

I always bring a book and my headphones with me on any day trip. You might be in a beautiful spot, but, if the peace of the moment is ruined by the people around you, headphones can literally save the day. 

5. Loneliness does strike, so be open to making friends

One reason I challenged myself to a solo trip was because I wanted to see if I could make friends on the road. In the past, I’ve been terrible at this because I’m far too shy and always assume people won’t want to talk to me, but then I can end up feeling horrendously lonely. But I’ve learned that most people are friendlier than we imagine they will be. While sitting at dinner alone, I noticed the woman on the table next to me was also eating by herself. I took a deep breath, introduced myself and we ended up having dinner together, exchanging travel tips and going on to a bar. It was a wonderful evening, and it was all because I smiled at her and said, ‘Hi’. One of the most important things I learned from this year was to make the first move; you’ll find most people are actually very open.

6. Always have an exit strategy

No matter where I go or what I do, I always have a ready-made excuse to leave if suddenly the situation turns or I need to be alone. That sounds extreme, but I find it empowering to think, ‘I’ll go to this event but if I hate it, I can leave.’ Knowing this is often the thing that gives me the courage to try something new. 

7. Have a friend meet you halfway through your holiday

Jess Pan

Jessica Pan

I love travelling somewhere alone for a few days and then meeting up with a friend for a few days. It’s the best of both worlds – you get to soak up everything with someone you really like, but you also get to have those transformative moments alone to really appreciate everything.

I never thought I’d like solo travel, but with these few adjustments, I’ve come to really love it. Throughout my year of extroverting, I did so many things that scared me: talked to strangers on the tube, performed stand-up comedy, went on friend-dates with strangers – but with every misadventure, I met amazing people along the way. And it’s even better when it’s in a foreign city full of potential.

Read about more of Jessica Pan’s misadventures in extroverting in her book, Sorry I’m Late, I Didn’t Want to Come: An Introvert’s Year of Living Dangerously out now.