Planning your first solo trip? Hurrah! You will have such a great time! Here are 13 things to consider as you plan your first solo trip to help you make decisions that will lead to a wonderful experience. FREE trip planning guide!

Taking that first solo trip

Well, look at you! You want to travel, and you aren’t waiting for the perfect companion to do it. You are going to have SO MUCH FUN on your first solo trip, and I’m here to cheer you on! You’re in for what I think is a deeper travel experience, as we notice so much more of the world around us when we aren’t distracted by conversation. Solo travel offers us rich, soulful experiences and opens up a whole new wonderful world.

I am so excited for you! Here are some things I’ve learned along the way traveling solo that can help you as you plan and go on your first solo trip. This is part of the Solo Travel collection on Wonder & Sundry. There’s a free travel planning sketch for you to use, too, so keep reading!

Big Ben
A snap from my first solo trip in 2004

My first taste of solo travel

I got my first little taste of solo travel in college when I flew overnight across the US from New England to the west coast for an off-campus program. It was one of those chaotic, cheap red-eye flights that we should only ever consider taking when we’re nineteen and healthy, but I was nineteen and healthy, and I found it absolutely thrilling.

A bigger taste in London

About a decade later when I went to London, I got even more of a taste of solo travel. I stayed at a friend’s flat, but I didn’t see much of her, as she worked the whole time (we did go to France for the day together). I wandered about London myself. 

As I navigated the Tube, explored, and stopped anywhere I found interesting, I discovered just how much I loved experiecing new places on my own. I even loved getting lost (these were the days of London A–Z, not Google Maps), because I always found something interesting along the way. I could stop and snap photos of anything I wanted to, and no one got annoyed with me (ask any of my friends—this can get old, fast).

First Solo Trip

London Eye, Hyde Park
Another snap from my first solo trip

Solo travel made me feel alive

Something about being alone in a sea of so many people made me feel so alive. I didn’t have to talk—I could just listen and observe. I felt excited and brave and serene and soulful at the same time. I can’t really explain it, but I knew that I loved it and needed more of it.

I haven’t looked back. Most of my subsequent trips I’ve taken solo, and I have had a blast on all of them, including a recent three-month journey in the Balkans. I’m here to tell you that you’ll love solo travel!

You’re going to go all by yourself? Why yes, yes, I am!

Solo travel has become increasingly common, and yet people still me how I can spend that much time alone. What am I going to do? Is it safe to do that? (Answers—what am I NOT going to do, and yes, provided that I take common-sense precautions.) If you’re thinking about your first solo trip, this post is for you.

Taking that first solo trip can fill you with wonder. A woman in a red polka-dot dress with a backpack on a narrow stone alley in Split, Croatia

Planning that first solo trip: 13 things to consider

Sometimes the hardest part of taking that first solo trip is simply deciding to do it. Solo travel is so rewarding, but lots of people feel daunted when just thinking about it. Here are 13 things to think about and consider when taking your first trip. I’ve divided this into a three sections—get excited (the fun part); how you’re feeling about your travel experience and spending time by yourself (so you’ll have the best trip for you); and the practicalities (what lets you have fun).

Spend a little time reflecting on these questions and do a bit of writing about them, as it can help to clarify thinking (and get you excited for your trip!). I have a worksheet you can use, as well, so please keep reading!

Click on the link to get the guide!

Get excited for your first solo trip!

1. What destination calls to me (and does not call to anyone else in my life)?

Do you have a destination you’ve always wanted to visit? I know I do. What about a destination where no one else in your life has any desire to see but tops your Wanderlust list? You may have just discovered the destination for your first solo trip!

If you haven’t already, start doing a little fantasy research on your destination (I love Pinterest for this—speaking of, are we Pinterest friends?). Check out travel blogs (like, say, this one) and find out more about what it’s like to visit there as a solo traveler.

I’m getting excited for you already!

2. What do I want to do there?

Now that you’ve done a little digging on what it’s like to travel there as a solo traveler, what kinds of things do you want to do in a given destination? Maybe there’s a historical site, or a dynamic café culture, or just a gorgeous beach that you would like to park your bum on whilst sipping something lovely. What about the food scene? Is there something you’ve always wanted to try but haven’t yet, because perhaps your friends aren’t into it? That can be especially fun.

Seriously, aren’t you getting excited?!

3. Where will I stay?

Especially if you’re traveling to a city, where you stay will make a huge difference in your trip. Some neighborhoods are more touristy than others, and there’s often one with more nightlife or known for a vintage street market, etc. How do you want to feel when you’re there? Do you long to be surrounded by the gorgeous old town, or would you rather experience a slice of life as it’s lived by the locals?

Read up on the different neighborhoods and discover which one you see yourself in. I’ve done both the lovely old towns and the slices of local life, and, depending on the destination, have enjoyed both. What I love best is a place that has some of the beauty that drew me there in the first place without being right in the thick of it. What about you?

Can’t you just see yourself in that charming apartment, looking out the window or sitting on your balcony with a glass of wine?

Wine, Lisbon


We all come to our first solo trip differently, and a little self-reflection can help to ensure that you have the best possible trip. The following are helpful things to consider.

4. How brave am I feeling?

When you think about taking a solo trip, how brave are you thinking? Overseas brave? A weekend a quick drive away? We’re all coming from different places, and there’s no wrong answer here.

You want to make sure that you’ll have a great time, so it’s important to be honest with yourself. You don’t want to be halfway around the world and terrified if a weekend away someplace close to home was the adventure you felt up to having. Or, maybe getting halfway around the world and being stretched is exactly what you need. Only you can answer that question.

5. How comfortable am I with my own company?

While we can and do meet amazing people when traveling solo, let’s face it. The solo part means that we will very likely spend most of our time by ourselves. So, do you spend time by yourself a lot? Do you like it? What do you do for fun?

If you haven’t spent a lot of time by yourself before, here’s some ways to help you learn to enjoy your own company and ideas for solo dates (it’s good to get some practice in before you head out). Use your time before your trip to practice having a great time on your own, and you’ll be ready when you get there.

6. What kind of travel experience do I have?

Is this your first solo trip, or your first trip, period? Maybe you’ve traveled the world, and this is your first trip you want to take by yourself. Or, perhaps you’ve never left home before, and you’re ready to take the plunge (well done, you!). When planning a trip, it’s always a good idea to have a sense of what you’re getting into.

Maybe you’re one of those truly adventurous types and have at it! However, if you’re not, then maybe you might want to have a gentler first solo travel experience. Or maybe not. It’s all up to you.

7. What’s my comfort level with risk?

How do you feel about taking risks? All travel is a risk, and solo travel incurs more risk than travel in groups. You are indeed on your own, and you need to think about your comfort level and gather data to make an informed decision.

Practicalities to consider ahead of your first solo trip

OK, now for some practical bits. Alas, not the fantasy of daydreaming, but taking the following into consideration will help make sure that you have a wonderful first solo trip.

8. How much of the language do I need to be able to speak?

If you’re traveling abroad, it’s likely that your intended destination has a different language. Do you speak it? For those of us in the US, including me, the answer is often, alas, a no (insert rant about the US education system here—SIGH).

If that’s the case, how much of it do you need to learn? For politeness, it’s vitally important to learn at least a few phrases, but some places require more language skills than others. Google Translate can really help, but, again, it’s important to know what to expect.

Different regions, different experiences

When I visited Santiago, I was grateful for my terrible high-school Spanish. Even though Chilean Spanish baffled me, I was able to make myself understood and could understand just enough to get by (well, high school Spanish and Google Translate). With the exception of restaurants and museums, English is not widely spoken there at all. I remember my halting conversations with the friendly doorman at my apartment with both amusement and a bit of shame.

Conversely, in the Balkans, I was embarrassed by how little of the language I learned in my time there, since English was so common. However, that’s because I mostly stayed in cities—had I done extensive travel in the countryside, I would have encountered a different language landscape.

9. Should I do a tour?

I’ve never taken a group tour before for an entire trip, but it’s something to consider. There are several tour outfits that cater to solo travelers, and some that are for solo female travelers. Tours tend to be much more expensive than traveling on your own, but if you would enjoy yourself more on one, then by all means, look into it.

Keep in mind that if you decide to do a tour with a tour company that doesn’t specialize in solo travel that you’ll likely pay considerably more than the double-occupancy price.

10. What’s my budget and how much time do I have?

Do some quick research on what kind of budget you’ll need for your trip. My ten-day trip to Finland, for example, cost more than a month in Croatia. Paris is more expensive than Buenos Aires. Eating and drinking in Montréal compared with Boston is pleasantly cheaper, but lodging was pretty pricey. It’s important to know what you’re getting into.

Remember to think about the time that you have to travel. That will have a huge impact on your ability to be flexible with your travel schedule and, obviously, your budget.

Quick-and-dirty flight/train/bus budget

When I’m considering a destination, I tend to go onto Google Flights and do a quick search for a roundtrip around when I was thinking about going, just to get an idea of the ticket price (I consider this a baseline and then look for deals). When you’re doing this, make sure to look at baggage limits and number of layovers, so you aren’t fooled by a super cheap ticket that’s 36 hours Chicago to London where you can take your toothbrush and that’s it when what you need is a direct flight and a checked bag.

Obviously, if you’re planning on traveling by train or bus, look up those prices instead. Given gas prices these days, it would be a good idea to do that if you were planning on driving.

Quick-and-dirty budget for everything else

Then I look up Airbnb and something like or Expedia to get a general idea of accommodation prices. If you have a definite timeframe in mind, use those dates. If not, ballpark it. I don’t usually travel to places where I need to rent a car (I do drive, but prefer not to), but if I need one, I look that up, too (don’t forget to look up the price of gas and factor that in!). It’s also important to ballpark travel insurance once you have these basics (yes, you need travel insurance).

Finally, I look at food and activity prices and do a little quick-and-dirty math. How does it look? Does it look like I could go and have a great time? Could I go if I decided to nix an expensive activity without feeling deprived?

Budget look good?

If yes, WOOHOO! However, if you can’t afford one destination right now, don’t despair. You may well be able to afford another without sacrificing fun. Repeat the budget process with that one.

11. How safe is this destination?

Your research into traveling solo for your destination probably gave you a feel for the general safety level, but individual experiences do not necessarily give the whole picture.

If you’re going abroad, check out your government’s travel advisories for a given country. As a US citizen, I tend to check the State Department Travel Advisories routinely. The UK Foreign Travel Advice also gives good information, and it’s not a bad idea to check a couple of different sources to get a good picture to help you make an informed decision. You may make a different decision than is recommended, but you will know what you’re getting into.

Health advisories are important, too

It’s also important to check on vaccinations and the like, especially if you’re traveling someplace that’s dramatically different from your home. I check the CDC Traveler’s Health for this. Some destinations necessitate vaccinations that should be administered well before travel, so check this before booking your trip. Note that you may need to use a travel doctor, depending on your destination (I needed to do this when I went to Argentina).

12. What are the entrance requirements (if going abroad)?

When planning our own travel, we’re in charge of everything, so it’s important to know the entrance requirements of our destination if going abroad. Do we need a visa? Proof of vaccination(s) (note: this isn’t just for COVID)? Proof of a return trip? Make sure you know what’s required before you book.

13. What are the transportation options?

How will you get around your destination? Would you drive? Fly/take the train or bus? Is there public transportation (and is it reasonably safe?)? How will you get from, say, the airport to your lodgings?

Do you need to rent a car when you arrive? If so, do you have a general idea of what the driving conditions are? Do you need an International Driving Permit if traveling abroad? Oh, and if you’re from the US, can you drive stick?

Vacation Photos

Do some general research on driving conditions, too

I had intended to rent cars while in the Balkans, but thanks to a delay in getting my physical license from the State of New Hampshire after moving from Massachusetts in August, I wasn’t able to get my International Driving Permit. I was fuming mad about it and feared that it would ruin my trip.

Once I arrived in Montenegro, I thanked my lucky stars that I didn’t try to rent a car there. While I can drive stick shift, I would have died on those twisty, narrow roads that require you to back up in order to yield to oncoming traffic. And that doesn’t even get to the aggressive drivers (understatement of the year). I feel faint just thinking about it. I took small-group tours for day trips, and I would do that again in a heartbeat, because I want my heart to continue beating, thank you very much.

Click on the link to get the guide!

I’m so excited for your first solo trip!

I am so excited for you and your first solo trip! While it’s important to do some reflection and research before booking your tickets, I hope that you find this helpful and that your trip has started to feel real to you. I’d love to hear from you about where you’re going and how you made your decision!

Free planning guide!

To help with your information gathering and reflection ahead of your first solo trip, I’ve put together a little free initial planning template for you. You can get it in a form you can print out and write in by hand or fill in on your computer. Simply subscribe below, and it’s yours!