Solo Female Travel Travel Planning

Beginner’s Guide to Solo Travel: Start Small, Dream Big

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Traveling solo is so exciting for me now, but it wasn’t always that way. And for many, it’s not like that at all. I talk to friends who wonder how I don’t get bored, if I’m scared, if I’m sad I don’t have anyone to share memories with. But there’s a beauty in sharing these things with yourself, spending enough time with yourself that you get to know yourself better. And some people want to travel solo, but the idea seems so daunting, intimidating. They ask, how did you get the courage to do these trips? The secret is to start small. If you want to get started traveling solo, here’s a handy confidence ladder to start doing solo things in smaller doses close to home, until you work your way up to a grand adventure far away. Read on for more details and motivation for each step.

For my full guide to solo travel for women over 35, start here →

A Confidence Trick No One Mentions

The less you pack, the more in control you feel out there on your own. Start with my free custom packing checklist. You’ve got this. 

1. Be a Tourist in Your Own Town

One of the biggest concerns I hear is people being self-conscious about doing things alone. Will people stare if I’m solo in a restaurant? Will I stand out among the couples and families in a museum? What will the bartender think of me alone having a drink? These are all valid worries – and I’ve had them too! The key is to get comfortable with this the way you get comfortable with anything – through practice!

Starting with a local solo day trip is a great way to practice how to travel solo

The good news is you don’t have to dine alone in a country far far away. You can do it in your own town! And it’s not just dining – see the sights, go to the theater or a museum, visit a park or the beach, go on a hike, have a drink, and yes, have that meal. Consider sitting at the bar for dinner if sitting at a table is still too intimidating. I do these things at home all the time and not only does it get me comfortable with being solo, but it also brings a richness to my life with all these fun activities, while also making me appreciate the place I call home. I live in San Diego, a tourist mecca, but just about every town has something you can do solo. What’s one thing you can do today to give this a try?

2. Take a Weekend Trip 2 Hours Away

Doing a solo weekend getaway lets you get a feel for being alone without being far away

After getting used to the solo bit, you can tackle the next part of angst – navigating public transport/airports/trains/foreign languages solo. Again, starting with something a bit more manageable takes this out of the equation. Find a spot a couple of hours away from home, somewhere you can drive to, and stay for the weekend. If that’s too much, try a night. Even a night away can help you see that staying in a hotel solo is not so bad, it’s actually quite relaxing. And the hotel staff? They’re not thinking twice about you being solo. They see it all the time. The only person worried is you!

You can simply enjoy the hotel pool, spa and restaurant, or decide to venture out around the town to see what it has to offer. Either way, you’re gifting yourself a wonderful weekend while testing out those solo travel chops. For me, weekends to Palm Springs or Orange County are fun little mini vacations that don’t take a ton of planning, travel or time. Where would you want to go to on the second rung of your travel confidence ladder?

3. Join a Group Tour – Solo, but not Alone!

If you're not sure how to travel solo, join a group trip so you can be solo but not alone

So, you’re used to the alone bit, and you’re ok staying solo in a hotel for a weekend. But the idea of going to a foreign country/boarding a plane/doing something more adventurous is still too daunting. This is where a group tour comes in! No, not the ones with 50 people on a tour bus. Thanks, but not thanks. I’m talking about small group trips, typically 14 people or less, with itineraries built for specific destinations.

Multi-Day Tours

I first did one of these when I wanted to see Machu Pichu in Peru and the Galapagos Islands in Ecuador. You could plan them on your own, but I was also interested in hiking, kayaking and the like, and decided it was easier to do this with a group. I was also doing marketing for a company that offered these tours, so I had to check out the product for myself! Not only did I fall in love with the format, but I fell in love with the people. The guides make you feel completely safe and cared for, and the other travelers become fast friends. This first trip was eleven years ago, and I STILL travel with some of the people I met on that tour.

There’s something about being with like-minded travelers, having these unique experiences, and being in a new place that brings you together and bonds you. That, and lots of laughs. Since that first trip I’ve done several others – three in different parts of Italy, one in Japan, Thailand, New Zealand – and all have been amazing. Just like the first trip, there’s people I connect with on the others that I planned trips with our met up with later in my travels – I’m about to see some this week when I visit England!

I can’t rave enough about this trip format, and this is coming from someone who wasn’t a believer. Well, consider me a convert! There are several companies to check out – Intrepid Travel, Salamander Adventures, Sage, are a few I can personally recommend.

How Many Days with Strangers (soon-to-be-friends)?!?

If a multi-day group tour seems a bit much, try organized day tours. Viator and TripAdvisor are good places to look for these. Look for ones that are small group – it’s typically easier to connect with others and not get lost in the crowd this way. Unless getting lost is what you’re after – then get on that big bus and enjoy! Everyone’s travel style is different, and all have their place!

4. Take Your Own Grand Adventure

Eventually you'll be brave enough to take a solo trip on a grand scale

By this point, you’re cool as a cucumber dining solo in a restaurant, feel calm instead of anxious cruising the streets of a nearby town as a tourist, and have traveled solo with the safety of a group. The only thing left to do is take your own solo adventure!

One way to do this is to add a few days on the end of your group tour, either in the final city of the trip, or somewhere on your route home. By this point, you’ve gotten to know the culture a bit, have likely seen some of the town, and have your bearings about you. Extending the trip by a few days is a great way for you to see things you didn’t get to, while trying out that solo travel prowess. I tend to do this on most group trips, as inevitably there’s something or somewhere else I want to see – and if I’m already all the way over there…yes, my justifications to travel are pretty ubiquitous.

See Two Places for the Price of One

I’ve also added stops in a different city along the way. Typically, this is because my flight is connecting through another city, and that city sounds pretty cool! Several airlines offer extended layovers for free – typically these need to short, 7 days or less, even shorter is some places. But it’s a great way to see a city that you might not have seen. I’ve visited UAE, Qatar, and China this way, and I’ve had friends do the same in Seoul and Iceland! Emirates, Qatar Airways, Icelandair and Korean Airlines offer these, and others likely do too. They even offer great rates on hotels and organized day tours while you’re there. It helps them drive tourism while allowing you to see somewhere new!

The highest run on the ladder is to go it alone the whole trip! This can be domestic or international, relaxing or cultural, nearby or far away. The key is continuing to expand that comfort zone from where it’s been. I’ve had relaxing days in Hawaii, fun weekends in New York, and cultural exploration in Italy – all very different but all amazing solo. That’s the other secret in all this – being alone doesn’t equal loneliness. In fact, some of my best trips have been when my only travel companion was Google Translate. So, pick that spot, board a plane or a train, give it a go. You’ll learn you’re stronger than you think, and you’re braver than you feel. Where would you want to go?

Conclusion

There are many ways, I'm here to help

Hopefully this gives you a game plan to try if you’ve been thinking about traveling solo but not sure where to start. Taking a grand solo adventure may not be for everyone, and that’s ok. At the end of the day, it doesn’t matter which rung of the ladder you make it to. It’s about confidence in who you are, enjoyment in where you are, and knowing you are capable of more than you may give yourself credit for.

Interested in traveling solo, but want more help getting started? Contact me for custom trip planning guidance!

Wherever you go, however you do it, I want you to have a trip to remember.

Happy travels, kindreds!

Ready to Start Traveling Solo?

There are two ways to keep going from here. If you want the full playbook on traveling solo as a woman, start with my Solo Female Travel guide, it’s everything I wish I’d known before my first trip alone.

And if you’re ready to take the leap but want someone to handle the where, the how, and the details while you enjoy your trip, that’s what I do. I’d love to help you plan your next solo getaway.

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