A solo trip can be daunting, unfulfilling, or dare I say boring. But over the years I've worked really hard to get good at traveling solo and hope to empower you with the tools to have a good time on your next one.
Solo travel is a gift. It’s one of my absolute favorite ways to experience the world and spend the precious time I have on this planet. It’s a wonderful adventure waiting to be embarked upon ripe with rich memories to be made. But this piece will not discuss the “why” of solo travel. I wrote about that last year. This piece you have before you now, my dear friend, is about the “how.”
Solo travel is a skill, one that can be strengthened and honed with a little bit of focus, research, and intention with just a dash of spontaneity and a pinch of self-awareness. It’s a very peculiar recipe, but I hope this piece will help you in planning your next lone expedition!
Darling, I’m goin need you to get a reason for your trip. A highlight. An anchor, if you will. Partially to have an interesting answer for the cute stranger at the jazz club who asks what you’re in town for, but largely for you to feel a sense of direction and intention. When you have a specific event or task you’re going to this city to accomplish, you’ll feel like you belong because you do. Wandering aimlessly can make you feel vulnerable, so make sure you have somewhere to go. A main event.
Until very recently, most of my solo trips have hinged on a performance I wanted to see. That’s typically my anchor from which the rest of my trip can sprout up and it often doesn’t even take up the entire trip. When I went to Chicago for Lollapalooza, I didn’t actually go to the festival for the whole time. I went to go see my husbands, Mick and Tyler, and explored the city for the rest of the trip. Those two very fine and musically inclined men were the anchors of my trip. They were why I went to Chicago, but I built an entire itinerary around their performances filled to the brim with things I knew I could enjoy all by myself. So if a cute stranger had asked me at the jazz club I went to why I was in the city (spoiler, no one asked me anything lmaooo), I would’ve said “Oh, yeah I’m here for Lollapalooza.” And called it a day.
This ain’t a group trip and it ain’t goin feel like one. It’s just you, friend. It’s just you and the wondrous destination you’ve selected. The massive part of this is to intentionally do things you will enjoy by yourself. Don’t go out and do stuff that’d only be fun in groups. Don’t do an escape room or rent a karaoke room by yourself. You will probably feel very lonely and bored. Instead, find things that are fun all by yourself or that allow you to meet other people.
My recommendations? Concerts, sporting events, museums, cooking or art classes, plays/ballets/musicals, fitness classes, self-care (saunas, massages, facials, etc), working out (a run, a walk, a paddle down a river), go grocery shopping and make yourself a rad meal, get dressed up and go to that restaurant you found on TikTok. Don’t overwhelm yourself either. Just do like 1-2 things per day that you’re really looking forward to or you’re really interested in and by the second day you’re gonna be like “Wait, wait hold up. Is this…a good time?”
Also, check in to remind yourself of what you already like doing. You like parks at home? Go to a park on your trip. You like cafes at home? Go to a cafe on your trip. Make your destination your home for a while.
Okay, but like minus all the crime. Don’t go to jail. What I mean by this is you’re gonna need some side missions. You have your main mission (your anchor) and then you have the other parts of your itinerary (the activities), but between those things are side missions! Every solid solo trip needs a few side missions.
Side missions are things that are kinda in the back of your mind that you’d like to do, but you don’t have to do. These aren’t reserved or booked ahead of time. They’re kinda like a if you get to them, you get to them, and if you don’t, you don’t
When I went to Tokyo for 48 hours back in 2019, the anchor was going to teamLab Planets (10/10 HIGHLY MF RECOMMEND). The side mission was going to Shibuya Crossing and the nearby store, Next Records. It was something I wanted to do, but it wasn’t necessarily written into the itinerary.
Same thing in Budapest, where the side mission was to find a good pair of jeans. I could’ve done it there or I could’ve done it at home. But I wanted to do it there. So when we had downtime or when we woke up early from a nap, we just started walking around on a casual hunt for denim jeans. We’d go grab lunch and just dip into the thrift store next door. We eventually walked upon a mall and I snagged my first pair of Levi’s there and I was overjoyed. Side mission complete. Idk it just adds a bit of fun and direction to my movements tbh. Granted, that wasn’t a solo trip, but still a very solid side mission example.
Other side mission examples: finding a specific item you’ve been trying to buy for a long time, swinging on a swing in a park, getting a specific thing to eat that’s not necessarily on the itinerary (an ice cream flavor you ain’t got at home), seeing a monument that’d be cool to see but you’re not pressed about it.
Get you 1-3 side missions, depending on the length of your trip, and you’ll be steady on the move!
So next time you’re thinking about going on a solo trip, make sure you have an anchor, a side mission, and solid activities that are aligned with how you already enjoy spending your time alone. Solo trips provide a unique opportunity to move in a way you just couldn’t do if you were with a group of people. It’s a bit difficult to make the most of that opportunity, but I sure do hope these tips have helped.
