How To Plan And Have A Kickass Time On Your First Solo Trip


Does the sheer thought of solo traveling unsettle your nerves? Do you ask yourself questions like, Why should I travel solo when I can travel with others? Will I feel lonely? Will I regret my decision? Will I be in danger? Will I come back alive?

I went through the same hesitations all the time. Is solo traveling for everyone? I’m not sure I can answer that, but I can tell you for sure, everyone should try solo travel at least once in their life. I took my first solo trip back in 2012 and it gave me whole new perspectives towards traveling and living my life afterward.

But before you read on, here’s a disclaimer so we’re on the same page: I’ve not taken as many solo trips as it may appear, so I’m only sharing what I know and learned from my perspective.

Here’s a practical guide to help you take that first step out towards your first solo trip.

Preparing for the Trip

Step 1: Decide the Destination

No one says you have to go somewhere you’ve never been. No one says you must fly to a place far enough to commemorate that first adventure. No one says you need to make the first solo trip a one-week or one-month length. It isn’t a competition, you don’t have to get over-adventurous if you don’t wish to. I personally feel that baby steps are good enough! A few days as a short trip is really very commendable already.

Here’s a helpful tip: Choose a city where you feel safe or a city where you have relatives or friends, or even a city you’ve visited before.

2. Book that Trip

Tip: To make it easier, have someone accompany you while you do the deed.

I had my friend stay on the line with me for moral support, till I clicked the “Book” button for my flight and accommodation. Of course, you have to find the right person who will encourage you instead of dissuading you from doing it.

When the transaction went through, I knew there’s no turning back.

3. Overcome Anxiety/Regret

After booking the trip, you might get overwhelmed by thoughts arising from anxiety, or perhaps even question your decision. I too have lost sleep after making a scary travel decision, wondering what I’ve done.


Stop for a minute and ask yourself, “What’s the worst that can happen?”

Halt any morbid thoughts of murder, terrorism, robbery or rape. The media often paints a frightening picture of a dangerous world out there. Indeed, it could well be a dangerous world out there and crooks can be everywhere (including your home city), but as long as you didn’t pick a place without basic awareness of conflicts and crime rates, if you’d exercised due common sense in selecting a destination, you’ll probably turn out fine. This world is really HUGE.

4. Research As Much As You Can About Your Destination

These are the general steps I always take:

  • Use TripAdvisor to get a general overview of a place, get key outlines to look out for.
  • Google thoroughly for deeper research on the key outlines. Use information from credible travel resources.
  • Check top travel blogs with relevant experiences and expertise.

5. Pack Properly

Packing the essentials will bring you peace of mind. For a first trip, I reckon it’ll be perfectly ok even if you overpack, be it clothes or shoes or medicine or even your favorite pillows that will bring you comfort.

However, do manage your expectations of places accordingly. For example, I’ve had to lug my luggage step by step up metro stairs and also narrow staircases at apartments, simply because not every train station and apartment in this world have lifts. Or sometimes they break down. Take note accordingly for your destination of choice.

6. Research 3G Options (if you really can’t live without the Internet)

In Singapore, we get access to high-speed Internet wherever we go. It is actually very impossible for me to imagine going through days without being online. If you really need 3G wherever you go, the general guideline is, research 3G availability options ahead for the cities you’ll be at.

There are some cities where you can buy prepaid data cards (eg. Bangkok, Johor Bahru, Hanoi, Milan, Seoul, Yangon); cities where you can rent a portable router (eg. Kyoto); cities where street WIFI is easily available (eg. Singapore, Seoul). There are also places where I couldn’t find prepaid data cards sold anywhere (eg. Athens airport, Santorini). Many cafes and accommodation providers also provide free WIFI in their premises.

Singapore’s airport has a service for Singaporeans called Changi Recommends, where you can rent routers if they’re available for the cities you’re visiting. I rented from them for Tokyo and also Taiwan.

If there’s no 3G guaranteed, I wrote a few useful tips to still travel effectively without 3G.

7. Tell Someone Your Plans

Don’t just scoot off and take off. Let a trusted someone (or a few people) at home know about your trip’s outline, destinations you’ll be at on which days. Pass that person a copy of your passport too.

This is more for reasons that someone at home will still keep a lookout for you now and then.

8. Mentally (& Financially) Prepare Backup Plans

Some people try Couchsurfing or Workaway and discovered their hosts are not anything they had expected. Or sometimes, things go out of plans and you need to leave a place quickly for your own safety. Ensure you have the means to make alternative plans, i.e, if you need to book an air ticket or a different hotel at the last minute, you should be able to afford it.

During the Trip—Adventure begins

9. Embrace the Freedom!

Say hello to traveling on your own terms: waking up at your own timings and only doing activities that you wish to!

10. It Helps to Keep to Some Rituals from Home

If you always have a morning coffee back at home to perk you up, feel free to keep to the habit on your solo trip. As for me, I don’t always do morning yoga back in my home country, but if I’m overseas on my own, I try to start my day with some morning stretches and sun salutations. It helps to keep me grounded in the new town!

11. Be Ready for New Eating Experiences from Traveling Solo

I feel you. Dining solo, even in a city where no one knows me, is not something I will be excited to do. Here are a few tips you can try to make mealtimes on your solo trips more comfortable:

a) Bring A Book / Kindle. Ever since I was a kid, I read books at meal-times. Now, I have my Kindle ready when I’m traveling solo and having meals at food joints.

b) Eat Mindfully. Yes, we don’t have to be occupied all the time. During my first solo trip, I had no WIFI nor was I that dependent on my handphone. It was perfectly fine for me to simply focus on that bowl of ramen right in front of me on the table.

There’re lots of benefits to mindful eating, by the way.

c) Pack and Eat Somewhere Else

Have a mini picnic on your own in front of the beautiful river you passed by earlier, or at the park, or perhaps your hotel room if you prefer.

12. Take Photos, Keep A Travel Journal

There was a time when most people around me didn’t like to take photos. With the development of social media habits, now, everyone everywhere takes photos. Regardless of your intentions, take photos for visual documentations of where you visited and things you did!

Also, when you’re exploring new places overseas on your own, it’s normal to feel the sensations deeper than say you’re traveling with a bunch of friends. I think a lot, feel a lot, and write them down in a journal at the end of the day if I’m not too tired by then.

At the end of the trip, I get an easy reference to the memorable incidents and places!

13. Handle Sleeping In A Foreign City Like A Boss

Sometimes, I find it extremely challenging to fall asleep in foreign places. What I do is to switch on my Headspace app for a 10 or 15 minutes sound-clip of guided meditation. My mind calms down so I drift off to sleep. The pleasant audio clip also makes the night’s silence a little less intimidating.

Because I also don’t like to sleep in the hotel room in complete darkness, I always bring a pair of sleeping eyeshades with me to block out the light as I sleep.

14. Stay Mindful of Surroundings

Practice common travel sense and be mindful of your surroundings. Watch out for pickpockets, thieves, any forms of tricksters and stalkers. Always be aware of where your valuables are kept and have your eyes or hands on them especially during unfamiliar scenarios, or when someone tries to distract you.

15. Stay in Contact with People Back Home

Feel free to take a full social media break if you want, but you should still stay in touch with some people back at home, and let them know now and then that you’re safe.

16. If You Feel Lonely, Know that You’re Never Truly Alone

You might be surprised to know that there’re lots of solo travelers out there, even in the most unlikely places such as Santorini, and in winter! Even if you might be alone at times, learn to enjoy your own company! It will teach you a lot about yourself.

17. Keep An Open Mind & Have Fun!

Stay open to new experiences — not everyone is out to cheat you (although you might meet into more than one who tries). Get to know different cultures and the people you’ll come across during your trip, the exotic food you’ll be having and embrace all the new sensations. Travel may be exhausting but it is also invigorating, and I promise you that your first solo trip will be a memorable adventure!

Hope this entry encourages you to take the first step out! Thought Catalog Logo Mark

Kristine is a petite wanderess, designer & yogi.

Keep up with Kristine on Instagram, Twitter and Website

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