The Type A traveler's guide to spontaneous fun

I’m the type of person who plans my entire life in advance. From what I’m ordering at brunch next Sunday to the exact hotel I want to stay at in Belgium two trips from now, no part of my life is left unscathed by my need for some semblance of control. In fact, I would argue my skills truly shine when I’m curating the perfect vacation. My last trip abroad included several meticulously planned documents, featuring screenshots of maps, alternative options in case something went awry and every single restaurant I wanted to try along the way. And, yes, I pack at least three extra outfits… just in case.

Needless to say, I’m Type A through-and-through—but my fiancé is far from it. Allowing spontaneity in my life–especially when it comes to travel—has been somewhat difficult, but not impossible. After 10 years and dozens of trips together, I’ve picked up quite a few tips that can help bring a little more impulsivity into your adventures, especially when you’re traveling with someone that’s far more Type B.

Whether you’re planning a last-minute summer getaway or an extended sabbatical across the globe, I rounded up some of my best tips and tricks to giving up (some) control while traveling.

If the success of your trip depends entirely on completing every single thing you pre-planned, you’re setting yourself up for failure. Fellow Type A travelers can relate to the disappointment when something doesn’t go quite right. Maybe that restaurant you’d been dreaming about is suddenly closed for a private event—or perhaps you pulled a me and got on the wrong train without a ticket and ended up paying a $150 fine.

The only way you’re able to not let these impromptu problems ruin your trip is by ditching the idea that everything has to go perfectly. Allow for mistakes. Be open to last-minute plans. You’ll be so much happier when you look back at the photos of your trip and realize that not everything went the way you thought it might, but you still had fun—and got a few mishap stories out of it.

I’ve lived in New York City for over 10 years, so walking everywhere is basically a habit—and it turns out that going on walks is one of the easiest ways for me to give up a little control while I’m on vacation. There’s a sort of magic that happens when you stumble upon an old church that wasn’t mentioned in any blogs or a quirky local museum you would have otherwise overlooked. Sure, it might take a little longer to get from Point A to Point B, but you might find the cutest locals-only café along the way that wasn’t even on your radar.

For these tiny moments alone, it’s worth it to lose yourself in the streets of a new city. I did this a lot when I lived in Prague to help better acquaint myself with the city and ended up finding the best tucked-away spots that weren’t jam-packed with tourists.

No matter how many Google searches and how much Instagram stalking you do, the best way to find hidden gems in any city is by talking to the locals. The last time my fiancé and I were in New Orleans, the bartender at Arnaud’s French 75 Bar wrote half a dozen of his favorite places on a napkin for us. It included restaurants and bars spanning far outside of the French Quarter, including a wine bar along the Mississippi with live jazz.

While I’m a firm believer in embracing the touristy aspects of different cities, locals know all the places that are actually worth your time and money (and probably don’t have any lines). Taking their recommendations in lieu of plans I’ve already made feels spontaneous, even if I am thoroughly reviewing each of the menus and reviews before I commit to changing said plans.

Alright, this one could be controversial. Sometimes I’m a little too obsessed with proving how much fun I’m having and making it look like I’m being totally spontaneous when in reality I took 200 photos to get the perfect shot and completely over-thought the corresponding caption. The thing is, disconnecting from social media (read: not posting until the end of the day or the end of the trip) can help you embrace on-the-whim plans. It also helps you evaluate why you’re planning on going to certain places. Are you going to the bakery with a four-hour line just to take a photo of a viral croissant—or are you okay with spending that time doing something else that might be more memorable, even if it wasn’t a part of your original plan?

The thing about being a Type A personality is that we constantly want to know what’s next. Where are we going? How long is it going to take for us to get there? Is it cash-only? Sometimes all our pressing thoughts and questions can be a little much for our travel partners that prefer to live life on a whim. For the sake of everyone enjoying themselves, it might be worth it to take turns picking different activities to do throughout the day. You pick the breakfast spot, they pick lunch, and so on.

Alternatively, you can both write everything you want to do on tiny pieces of paper, put them in a bowl, and build out your vacation in a way that feels a little less formulaic.

I know, it’s a terrifying thought, but staying true to your beloved Google Sheet vacation is the death of spontaneity. So, I double-dog dare you to leave at least one day plan-free until you arrive at your destination. Learn what the city (or country) you’re in is most well-known for and then book a last-minute tour or cooking class to experience the local culture more authentically. I did this on a free day in Italy’s Cinque Terre and ended up at a private pesto-making class with unlimited Champagne and a recipe that I still use to this day. It was one of the most fantastic impromptu plans ever and I can’t say I regret ditching my original plans to do it.