Why you should plan a repeat trip to a familiar place—alone
See reliable old favorites in a whole new light.
I grew up in Wisconsin, went to college and met my now-husband in Iowa, and have a decade's worth of roots in Brooklyn. But I have another home—one I’ve visited 13 times over the past decade or so—that’s 2,600 miles from where I sleep at night.
Not many days go by when I don’t think about living in Reykjavik. More a thought exercise than an actual plan, the daydream is anchored by memories from trips with friends—plus one elopement on an exceptionally rainy Summer Solstice 2022. But it took me eight years after first setting foot in Iceland to finally visit my favorite city solo.
People around me didn’t get it: “Why not go somewhere new?” they asked. But solo trips in your “home away from home” are the ultimate test of confidence; in my experience, they also leave you with a new perspective on a place you already know so well.
There’s so much to learn when you dig a layer (or five) deeper on a solo visit to a repeat destination—you’ll be surprised (like I was) to feel like you’re experiencing an entirely new place. Here are a few tips that helped me along the way.
Plan an ‘been there, done that’ day
The concept here is simple: Fill one day with the things you know and love. It can help get you centered and serve as a little “you’ve got this; you’ve done this before” pep talk.
For me, solo in Iceland, that means visiting the library at the Nordic House. Designed by Alvar Aalto, the interiors are minimalist; there really isn’t too much to do, so I usually bring a book and settle into one of the comfy lounge chairs. From here, it’s onto shopping at Fischersund and Rammagerdin, walks along the harbor, and dinner at Hosiló. Knowing what to expect allows me to let my guard down and fully prepare for the trip ahead, whatever it may bring.
Lean on one—and only one—repeat restaurant
Maybe you loved a restaurant for its great playlist and niche menu when you first visited with friends, but a repeat solo visit can unveil a cozy nook with a table for one or an especially great people-watching perch at the bar. It can be way too easy to only dine at spots you previously liked, but challenge yourself to a single repeat and plug your other meals with new places. After all, you can tell a lot by how a restaurant treats its solo diners.
Once, at the subterranean wine bar Vínstúkan Tíu Sopar, I watched tables fill up with groups and crowds descend onto the small bar for natural wine. After being told to sit at any open table, I realized the only available space was a four-top in a corner. Nervous about taking up so much space in a busy spot, I sat down reluctantly. It wasn’t long before a few friendly strangers joined me—thus proving my fear unwarranted.
Do at least one thing that challenges you
I’m committed to doing something that scares me (just a little bit, in a good way!) on every trip; I highly recommend this as a general travel practice, particularly when you’re solo.
On my first solo vacation to Reykjavik, I booked a spot on an Inside The Volcano Tour, which (safely) brought me into the belly of a dormant magma chamber. Scary? Sure. But I now have some incredible memories that I created entirely on my own—a huge confidence-booster in itself.
Become a regular
There’s a bit of armor every solo traveler wears—you’re away from home, your guard is up, and you’re not entirely open to talking to strangers. But there’s nothing better than hearing your name called from a sidewalk so far from home, only to turn around and see a friendly face.
How does it happen? In part, the way it does in everyday life: by becoming a regular. Commit to a cool, new-to-you restaurant, cafe, bar, or shop; you’ll find that even a few repeat visits in a single trip can seed actual relationships.
Case in point: on one of my first visits to Kiosk, a shop run by a group of women in the local design community, I struck a conversation with designer Anita Hirkelar. Trip after trip from that point on, I ran into her, always greeted with a smile and a quick life update. I slowly got to know the other designers in the shop just by popping in to see what was new. And thus, my own little “community” was born.
Skip the car rides as much as possible
I don’t love driving, and the idea of navigating the many roundabouts between Keflavik International Airport and Reykjavik alone isn’t my idea of fun. So whenever I’m in town solo, I go all in on walking. As someone who is able bodied, I’m able to do this comfortably and I don’t take that for granted.
In addition to quashing my biggest solo-travel stressor—the very idea of renting a car—being on foot has also helped me notice details I might have easily missed if I were whizzing by. Some favorite memories: Stumbling across the Vatnsmyri Bird Sanctuary while walking to Nordic House one fall day and finding a beautiful shortcut through the Hólavallagarður Cemetery en route to dinner.
