10 tips for planning your first solo travel trip
Photography by Teal Thomsen
The idea of setting off on your first solo travel trip can be an intoxicating mix of excitement and anxiety. All the choices are yours but…all the choices are yours.
And for most of us used to traveling with friends, family, or partners, it can feel a bit daunting or even selfish to take the time out for a trip just for us. As women especially, we’ve got the added narratives around female solo travel and safety to get past.
All that said, anyone who’s made the leap can attest that the freedom, confidence and strong sense of self that come from taking the bold step into the world of solo travel makes it 100% worth it. There’s nothing like having an entire day to spend as you wish. Three hours browsing a local book store? People watching at a cafe? Starting that novel you’ve always wanted to read, from your sun lounger? Solo travel is the perfect opportunity to step outside your day to day obligations and focus on you.
As someone who got hooked on solo travel a bit later than many, here are my go-to tips for planning your first solo travel trip.
1. Try out a place nearby
You don’t have to quit your job and move to Bali to give solo travel a go (though if that’s your thing, absolutely!). You can get a lot of the same benefits without an expensive plane ticket. Open a map and check out some places within driving or train distance from where you live and book a weekend away just for you. The advantages? Logistics are much simpler — no need to learn a new language, you’ll already be clued into cultural norms, and you won’t even need to think about a SIM card for your phone.
Your first solo travel trip is going to be a lot of trial and error. Going somewhere close to home can give you a soft landing. You can even take the first step in your own city by taking yourself out to dinner in a different neighborhood, or popping into a museum you’ve never been to on your own.
2. Add time on to a business trip
This is how I got my start in solo travel, and it’s a great (budget friendly!) way to explore a new place. Are you traveling to visit a client or heading to a conference? Check out tickets to stay the weekend, leaving a day or two later. If the flight is the same cost and you cover your own hotel, many companies won’t have an issue with you heading back on a different day. A night or two of hotel costs is a small price for a holiday abroad.
As a bonus, if you add the time to the end of your trip, you’ll already have had some time to get your bearings. You can ask those you meet with on your business trip for recommendations on where to eat, and what to see or do after your trip. I’ve always found my colleagues to have the best recommendations – after all, we know each other, and they live there!
3. Choose a walkable city
It’s difficult to get bored when you’re surrounded by shops, museums, galleries, and restaurants. I love mid-sized cities where you can walk everywhere without the hassle of learning the public transit system. And sometimes the best discoveries will happen along the way – a newly opened wine bar that hasn’t made it on Google Maps, or a pop-up popsicle stand that you discover on your way to dinner.
For picking a neighborhood to explore, I’ll often pop open Google Maps. Zoom in and look for the yellow shaded areas. These indicate high foot traffic, and tend to be good spots to wander. You can also search for sub-culture neighborhoods, like Chinatown or Little Italy. San Francisco’s Japantown is one of my personal favorites.
4. Have a purpose
This could be bringing along your camera, a book you’ve been wanting to get through, or a list of top bakeries to compare their interpretation of the croissant. Having a mission will help get you out of your room, give you a specific place and activity, and something to share back on when you return.
My personal favorite? Researching local wineries and booking in a tour to learn about different winemaking techniques and cultures. Even when there’s a language barrier, we both have a shared love and understanding of wine that helps us get by. It’s a great way to really see how connected we are. Plus you’ll learn some cool cultural takes – like how Sancerre is made in giant concrete eggs in France, or the batting-cage like nets that protect grapes from hail in Mendoza.
Photography by Teal Thomsen
5. Try working remote
If you’re worried about getting bored or lonely, bring your laptop along. Do a search for co-working spaces in that city in advance — some even offer live-work combinations. Having a co-working home base for a week or more can also help you find a community of other travelers, and pick up some great recommendations on the way.
Some great places for digital nomads include Lisbon, Bali, Austin, and Buenos Aires.
Join the waitlist to check out our local’s guide to Lisbon and other female solo travel destinations.
6. Book a day tour
While time alone is great, sometimes saying “table for one” can get a bit lonely. Check out Airbnb experiences, Viator, or search for “tours + [topic] + [city]” on Google. Look for tours by locals in your native language — it can be a fun way to get to know the culture, food, art, or nightlife. Small group tours with locals can often give you exposure to places you wouldn’t necessarily feel comfortable popping into on your own.
Tip: if you book online in advance, you don’t have to worry about exchanging cash at the tour itself (though I always like to keep a few small bills in case tipping feels appropriate).
7. Learn a new activity, hobby or sport
Have you always been interested in photography? Always wanted to know how to surf, or super into yoga? You can often find places with week-long local programs that give you the chance to try out a new interest and meet a group of people along the way. Personal shout out to Selena’s surf packages in Santa Teresa that are great for beginners.
Photography by Teal Thomsen
8. Make plans to meet up with someone
It could be an old friend from university, a cousin you haven’t seen in years, or a friend of your mom. Traveling solo to a new city is a great excuse to look at your network and see who you might know in the area. Most people are happy to welcome you into their town, and share some local recommendations. And who knows, you just might end up with a new (or newly reacquainted!) friend out of it.
9. Bring your running shoes
Don’t enjoy running? Doesn’t matter. Pack a pair of trainers and ask the hotel concierge for a good route. Runners are notorious for getting off the beaten path, and planning a scenic run across the city will likely take you through some beautiful parks and neighborhoods outside of the tourist zone. No worries if you walk the entire thing either – no one’s there to judge!
A personal tip, I always pack my flip belt. It fits easily under a loose t-shirt and holds my phone and hotel key. This way you don’t have to worry about flashing valuables if you happen to turn down a slightly uncomfortable street. I’ve even used mine on travel days when I want to keep my wallet close to me and not have to keep a constant eye on my purse or backpack.
10. Follow your curiosities
So many times holidays become about shared experiences — and that’s great. But the magic of solo travel is you get to focus on you and your own interests. Pull up a map. Zoom into areas you know nothing about. Get inspired by books you’ve read or movies you’ve seen. Daydream about trekking through the alps, lounging on a beach in Brisbane, or discovering the best ramen of your life at the tiny counter of a second-story Tokyo restaurant.
And the best part? It doesn’t matter if this daydream isn’t interesting to anyone else — it’s yours. Solo travel gives you the space and the freedom to follow your interests, and maybe discover something about yourself along the way.
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Photography by Teal Thomsen
