How To Plan A Solo Trip

Traveling alone is one of my favorite things I’ve learned to do in my twenties. The experience of getting on a plane, landing in a new town, and learning my way around has become a healing, fulfilling practice. But, like any habit you want to build, it does take practice and some forethought.

But once you do have your strategy in place, you’ll be able to use your framework to travel across the world or across the nation. I’ve used the same strategies to explore everywhere from Dublin to Washington D.C., Nashville to London.

Tackle all the reasons you would not do it

I live with anxiety and this is one of the areas where I see my anxiety (and imposter syndrome) surface the most. I tend to tell myself that it’s too scary for me to travel alone, that I don’t have the money, or that I’m not worthy of these experiences because X person can’t do it too. My way around these blocks is to tackle them one by one. I’ll take a clear look at my budget and price out how much I can spend on the trip, as a way to prove that I can afford it. I do the same with any feelings of unworthiness or fear that surface — I make sure that my boyfriend knows where I’m going, I have my location on, and I also set some time aside to write out affirmations that help me feel more grounded in my decision.

Give yourself both an out and a locked in reason to go

My most recent solo trip was to Nashville this past August. Before I even bought a plane ticket or booked a hotel, I bought a seat at a writer’s round I wanted to attend. Knowing that I was going for something specific helped center my first solo trip in years. It gave me a locked in reason to follow through, while also providing enough flexibility that I could make it as long or as short as I wanted it to be. For many people, especially if you’re just starting to travel alone, making your flights refundable or waiting to book your hotel until a week before, can help the travel feel less intense.

Plan your itinerary based on your interests, NOt the internet’s

When I went to Nashville, I did not have BBQ, go to any museums, or do a night out on Broadway. Two out of three of those things are things I’d love to do the next time I’m back, but when I sat down to think through what the purpose behind this solo trip, I realized that it was more about recharging creatively. So, instead of tiring myself out, I thought about all the things that make me feel full, no matter where I am. I sat at coffee shops, read, sat at the hotel bar, and went to the writer’s round. I spent more of my “travel fund” on the nice hotel room since I knew that I wasn’t going to spend it on touristy things. Setting your purpose for a trip means that when the time comes to tell others about it (either in person or on the Internet) you won’t feel the comparison game as much. You won’t feel like you visited a city the “wrong” way simply because you visited it “your” way.

No matter where I go, I tend to plan my trip around coffeeshops and bookstores. I’ll learn my way through new neighborhoods by following my Google Maps from one shop to the next. Along the way I’ll stop at local eats or ask someone to recommend their favorites. I know that traveling is a luxury, especially if you’re first generation like me or have a slew of other responsibilities to manage, but I also think it can be a form of self-care that, if you can, you shouldn’t feel bad about allowing yourself to have. I tend to spend money on those experiences more than I would clothes or makeup, we all have our own interests and traveling solo can be a fun one if it’s up your alley.

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