How to Plan the Perfect Solo Trip (Part 1)
or, i refuse to edit a document down to a normal length
When it comes to traveling, I’m the Planning Friend. If we’ve ever traveled together, you can attest to this—I will come to you with a long list of carefully-researched things to do and see in each city we’re going to. If someone tells me they’re planning to visit a place I’ve already made a list for, the list WILL be sent to them. This all started a few years ago when a friend asked me for recommendations on what to do in New Orleans, a city I’ve been to twice. The resulting email, which begins like so, catapulted me into the delusion of thinking I’m great at planning trips.
Since the only place I ever traveled as a kid was that most azure coast of the Eastern Seaboard (the Jersey Shore), I got a late start in learning what to actually do on vacation. My vacations consisted of walking to the Seaside Heights boardwalk, soft-serve cone in hand, and begging my mom for $3 to play the game where you hit a plank with a hammer and launch a disgusting rubber frog into a pond of stagnant water that definitely contains flesh-eating bacteria. What was I supposed to do in, like, London?
When I moved to Madrid and started traveling more often, I came up with the idea of actually doing research before my trips, which led to haphazard lists and screenshotted ideas of things to do. But once I took my first-ever solo trip—to Valencia during the Covid summer of 2020, my cloth mask era—I got serious about planning. I made a list so detailed that I couldn’t possibly be bored for a second while alone there. And from then on, I started learning what it takes to have a perfect solo trip. I took another one. And another one. Until here we are, a bunch of trips later.
In my last newsletter, I said I would create a guide to planning a successful solo trip, so I’m going to do that now. The task has become bigger than I expected it to (definitely not due to my obsessive need to include every detail rather than trim things down), so this Part 1 is going to be about how to create your giant list of research before you go. Part 2 will be made up of tips to follow once you’re actually on the solo trip.
Get out your Notes app, get ready to have the time of your life without having to appease anyone but yourself, and just try to trust me here!
The List
Okay, okay, I’ve hyped this up too much to bury the lede.
Whenever I’m going to a new city, I make a note in my Notes app for that city/area only. I start with basic research on TripAdvisor, Instagram, TikTok, travel blogs, etc. in order to get a feel for what I’d like about the place, which usually starts with me Googling “best cafes lisbon” or something like that, then spiraling outwards from there.
I always make multiple bulleted lists inside my note, using the categories below. While adding places to the lists, I write down which neighborhood or area they’re in, which I’ll use to organize them later:
Cafes and brunch spots I want to check out
I am nothing if not a brunch and coffee bitch, so when I’m traveling, my most urgent need is to find a place to get food and coffee to start my day. These are also excellent places for just sitting down and spending time reading or journaling or whatever it is that relaxes you. When I’ve got nothing concrete to do, I can spend a couple hours in a cafe chilling and planning the rest of my day.
I typically start my search on Google, looking, as I said, for “best cafes/brunch [city].” This leads me to travel blogs with exhaustive lists on cute, cool coffee spots (with photos). When a blog recommends somewhere that I think looks good, I Google the place and find out (1) if it’s still open—Covid destroyed a lot of small businesses that tend to not update their Google listings, (2) if I can see the menu, and (3) if I can find its Instagram, where there will inevitably be pics of the food. If I’m still interested, I add it to my cafes/brunch list. I also look up its location and write down its neighborhood, days/times it opens, and how far it is from where I’m staying, on foot or by public transport. Do this, seriously! That way you have an idea of which things on your lists are close to other things, so you can plan accordingly.
Just to note, TikTok is a great source for things like this—there are tons of videos made by tourists and locals alike about the best cafes, brunch, clubs, restaurants, and more in each city. I use it a lot as a travel resource and have discovered great places through it.
Restaurants to eat non-brunch meals in
When I go on a solo trip, I relish eating brunch alone. I love the feeling of pretending to be a Mysterious Local Eating Eggs. No one knows who I am, the city is full of possibility, and servers are extra nice to women eating alone. Plus, I can eavesdrop more easily.
As much as I love solo brunch, I get anxious when I think of eating dinner by myself. For me, it’s the difference between being alone and feeling alone. At dinner, sometimes I look around and see other people with their families and partners and friends and feel absolutely awful about myself. I wish I was with people who I could talk to and laugh with and enjoy the meal with. I want someone to compliment my outfit! Compared to the scarce attention I get at a cafe, when I’m alone at dinner, I feel like everyone is watching me and…I don’t know, making fun of me? It’s not remotely true—and I’ve gotten a lot better at it with practice—but I still get Nervous Stomach when I do it sometimes.
That’s why this category is extra important for solo travel! When you look up “best restaurants [city],” you need to gauge whether or not the places you find look like places where you could eat alone. Technically, you can eat alone at any restaurant (please don’t let me stop you!), but there are some that I look at and just know I’ll feel anxious or sad if I go by myself. It’s a subjective thing, so it’s up to you to read that room. I like looking up restaurants on solo travel TikTok accounts, or reading reviews to see if others have gone alone or if the vibe seems chill.
Definitely remember to look up price points and opening times! Coming from Madrid, I got used to starting dinner at like 10:30 pm, but in some cities, restaurants close before that.
I tend to look up way more brunch places than dinner places, since I like starting my day knowing where I’m going and that there’ll be food there. I’ll put a handful of restaurants on my list, but I also like just winging it and looking up nearby restaurants when I’m ready to eat.
Historical/cultural things to see and do
Not everyone is into sightseeing, I get it. You get to choose how much history or culture to absorb on a solo trip. It’s actually so much fun to go to a museum or monument when you don’t have to adhere to anyone else’s schedule; you can approach it at your own pace. There have been times when I’ve been to a museum on a trip and walked right back out after not liking it for a few minutes. There have been other times when I’ve spent 4 hours looking at art and doing audio tours and getting lost in the sauce.
If you are into this stuff, you can start like I do—looking up “things to do in [city].” Broad, I know. But that usually yields lots of results on historical things to see, as well as places off the beaten path. You’ll find posts like “15 Sights You Need to See in Paris” alongside posts like “25 Things to Do in Paris We Bet You’ve Never Heard Of.” I comb through lists like that and add the usual info: name, brief description, neighborhood, opening times, and distance from where I’m staying. I like to look each of them up on TikTok and TripAdvisor to get a feel for them. It’s also helpful to go through the top-ranked things to do in that city on TripAdvisor.
Want some ideas for historical and cultural things to do on your solo trip? I like museums, art exhibitions & galleries, parks, street art, tours, monuments, seasonal activities like Christmas markets, plazas, historic districts, iconic stores, things like that.
Nightlife (bars and clubs) you’re interested in
Maybe you don’t go out much, and especially not alone. Even if you don’t—or don’t drink—I still encourage you to try going out alone on at least one of your solo trips. Obviously, there are plenty of factors involved. For women especially, it’s not always safe to go out alone, moreso if you’re drinking or need to find a way home at night. As usual, I read the room when I go out in a new city. Is it more of a “party” city where it’s socially acceptable to go out by yourself? Am I staying in an environment (like a hostel) that means I’ll probably meet people to go out with? Is it safe at night? Will I feel sad?
For example, in Berlin I had no problem going out alone when needed. I was far from the only one by myself, and the environments I was in were respectful and safe. It was also an easy city to meet people in. But in a city like Naples, I didn’t want to go out drinking alone. It didn’t seem to have a “culture” of women going out solo to party like Berlin does, and although I didn’t feel unsafe at all, I wasn’t totally comfortable with the idea of walking through the streets by myself at 4 am if I had to.
The types of bars or clubs you put on this list are up to you. When traveling solo, I prefer divey and old-school bars. I look up bars around where I’m staying and in the neighborhoods I’m going to check out. When looking up clubs, I usually do so under the assumption that I’ll meet people on the trip who will also want to go to clubs, since I’m less inclined to do that alone. I’m not super into huge Euro clubs packed with study-abroad students, so I research places that play music I like to dance to. Best resources for this are TikTok, Instagram, and Resident Advisor.
I use Resident Advisor to find parties or DJs that look fun in the city I’m going to, and the events they post there are usually the type where it’s either fun to take the friends you’ve just met or safe to show up solo. I’ve done both! The RA app lets you save events to a calendar, so once you’re on your trip, you’ve got this whole little nightlife calendar of possibilities.
Shopping (stores or areas)
I like need to shop when I’m in a new place. I don’t typically buy touristy souvenirs—I do like them, but it’s not good to have too many in my apartment, or else it starts to feel like a museum. My favorite vacation shopping has always been at vintage and thrift stores, so those are what I look up first in this category—their Instagram accounts are really helpful if you want to see what type of clothing a vintage store usually sells and whether it’s your style or not.
Lots of cities have main shopping areas if there’s a bigger store you’re looking for. I like to see which mega-companies are native to the country I’m visiting, so I can hopefully get things cheaper than in my home country. It’s like when people from the U.S. come to Spain and see that Zara is wildly cheap there compared to the U.S.—it’s a nice surprise! Main shopping areas can be good for getting a lot of shopping done in one go, too.
I also tend to look up concept stores or design stores when I’m in a new place. Jury’s out on whether I’ll be able to afford them, but lots of places have surprisingly decent ones. I love using Lisbon’s LX Factory as an example—it’s a huge complex full of street art, concept stores and boutiques, and cute places to eat or have a drink.
Pro tip: some of the best souvenirs come from museum gift shops. I’d much rather have something that reminds me of a piece of art I saw on my trip than a keychain that says the name of the city. They’re also great for finding gifts for other people.
Lastly, I love looking for bookstores wherever I’m going. If I buy a book on a solo trip, I’ll always be reminded of the trip when I see it. I like having extra new books to read during my stay or while traveling back home, too! Lots of cities have very cute and cozy local bookshops that you can spend hours browsing…another thing that’s usually better done alone.
Neighborhoods that look notable
Every city has neighborhoods that appeal to different people—let’s use NYC as an example. Maybe you’re into designer shopping and luxury goods, so you go to the Upper East Side or SoHo. If you want bookstores and aesthetic cafes and an underground show that makes you feel like a local, you go to Bushwick. For sightseeing, you head to Midtown or the Financial District.
I like to get a feel for the neighborhoods in a city while I’m putting my other lists together. The resources I find about restaurants, cafes, etc. will surely mention different neighborhoods and what their reputations are. Then, when I’ve noted down the neighborhoods that look interesting and/or contain the highest concentration of places on my lists, I go to Maps and locate them geographically. I make a mental or literal note of which neighborhoods are near each other, which ones are too far for me to walk to, all that. This helps me so much in editing my lists and getting my bearings once I get to the city. I also then re-order my lists in order of how close things are to how far they are from where I’m staying, but you don’t have to reach that level of insanity.
I’m going to stop here for now, because I feel like this is my manifesto and I couldn’t stop typing until I got it all out. Of course, you can take and leave whatever you want from this guide, depending on what you want your solo trip to be. I’ll get to Part 2 soon, which will go over all the things you can do while on your trip to make it fun and easy and comfortable. Until then, feel free to send me questions or feedback or whatever (you can respond to this email or leave a comment), and I’ll see you on my next sleepless night.
Kim