How to Plan Your First Solo Trip

So you’re thinking about taking the plunge and finally booking your first solo trip. Maybe you’re tired of waiting around for others to join, or you’ve just realized how much you enjoy your own company. Well as a woman who has been on several domestic and international solo trips, I’m here to give you some of my tips on planning your first solo trip. Below are some questions you can begin to ask yourself while in the planning process.

Exploring the islands of Greece.

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What kind of experience do I want to have?

Before you pick your destination, think about what type of experience you want to have. Do you already have a dream destination in mind? Perfect, book that if possible. If not, what sounds like your vibe and what locations will be able to provide that experience for you? Do you love cities and want to explore a new one? Are you looking for a relaxing beach vacation? Do you prefer being in the mountains or hiking? Do you want to do a mix of these? Start by asking yourself what type of trip you’re looking for, so you can begin narrowing down your destination ideas.

Beautiful turquoise water and palm tress at a beach in Tulum, Mexico

What if I don’t want to go far from home?

If you’re nervous about being far from home by yourself, consider planning a trip that isn’t too far from home, whether it’s domestic or international. For example, I live in New York. So maybe if I wanted to explore a new city, instead of Paris or Tokyo, I could pick Montreal or Chicago. If I was craving a beach vacation, instead of Australia, I could start by going to south Florida or Aruba. Think about some relatively close destinations that will be able to give you the type of experience you’re looking for.


What if I don’t speak multiple languages?

I get why this can be a concern, but it’s not usually a huge issue if you mainly travel to cities or popular tourist destinations. English is widely spoken around the world, but you could also simply choose to go somewhere that it’s more commonly spoken, like The UK or Canada. Or if you also happen to speak Spanish, you could choose to go to Spain or Costa Rica. But generally, Google Translate and sticking to more touristy destinations will do the trick.

My metro card in Taiwan, with Pokemon characters pictured on it.

How will I stay safe?

How do you stay safe normally when you’re out and about by yourself? That’s how you’ll do it abroad too. Generally, unless you’re going to a place that is notoriously unsafe, you’ll be fine as long as you take precautions like being aware of your surroundings and not telling strangers where you’re staying or that you’re alone. If someone asks me if I’m alone, I will usually lie and say something like my friend decided to stay back at our hotel because she had work to catch up on or wasn’t feeling well.

Do a bit of research about what the most common safety concerns are in that area, so you can feel prepared. For instance since pickpocketing is common in some European cities, I packed a bag that could be held close to my body and a mini carabiner to make it more difficult for someone to open it without me noticing. Just use your common sense, like not carrying your phone in your back pocket or getting black-out drunk, and you should be fine.

Another safety precaution I like to take is booking travel health insurance, just in case anything were to go wrong on my trip, otherwise it at least gives me some peace of mind. I personally use the SafetyWing Nomad Insurance, because you can pay either by the dates of your trip, or monthly if you don’t know how long you’ll be traveling.


What if I get lonely?

You might, I have before. But this is a chance you have to sit with that feeling, notice how you respond to it. Do you reach for your phone? Or do you allow yourself to sit with it for a bit? You can always call or text a friend or family member and tell them that you’re thinking of them and how things are going, just like you would if you were feeling the same way back at home. But I personally think it’s healthy to learn how to enjoy some alone time. After all you’re in a new place with no one else to answer to, which means you can basically do whatever you want at any time!

Some of the ways I avoid feeling lonely on a solo trip is by booking hostels or guest houses, where other guests are likely to be solo traveling and in the mood to socialize. For hostels, I typically use the app Hostelworld, or you can search hotels via Google Maps, if location is the most important factor to you. Hostels will usually offer the option of both private rooms or shared rooms with other travelers. I often stay in female-only shared rooms, since this makes me feel more comfortable. I’ve met some really interesting women that I still keep in touch with years later by doing this!

You can also book a tour and strike up a conversation with other tourists, or even the tour guide. I personally like GuruWalk, which provides free walking tours in numerous cities around the world. It’s a great way to learn more about the location you’re visiting while meeting new people. Just make sure to bring some cash to tip your tour guide at the end!

Alternatively, you can book a group tour or retreat, which means you’ll be traveling around and staying with the same people throughout the trip, making it easy to socialize and hopefully make a new friend or two. A lot of social media influencers host group tours, so Instagram and TikTok is where you’re most likely to find these. And retreats are often based on a common interest, like yoga, surfing or co-working. For co-working retreats, I can personally recommend The Better Neighbors, which currently hosts retreats in Spain and Romania.

Delicious food I enjoyed with other guests while on a vegan group trip in Greece.

Just book it!

I hope this blog post has eased some of the worries you may have had about booking your first solo trip. Even though I solo travel all the time now, I was absolutely terrified at first! But being scared to do something, doesn’t always mean you shouldn’t do it. Think about you 10 years from now, would you be glad you went? Most likely you will, I know that’s how I feel for sure! And if it’s the actual travel part that stresses you out, be sure to check out my post about my essentials for less stressful travel next. Happy travels!

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