1. Choose your destination carefully
Let’s face it: if you’re going to an amusement park (we all know planning is a must at Disney …) or a continental cosmopolitan city full of must-see museums or other historical sites, You won’t be able to let go of your planning tendencies. Choose your destination to keep the vibe relaxed and cool. To me, that’s a lovely home on the beach. For you, it might be a cabin in the woods or a mountain cabin. Keep it low-key, cute, and classy, and you’ll be more inclined to soak up your surroundings instead of running from point A to point B every day. I also find it helpful to focus on natural beauty rather than man-made wonders. In doing so, you’re less likely to start sketching out your daily, can’t-miss itinerary.
2. Rough outlines are ok
I know I know. I’m just telling you to ditch the schedule as much as possible. That said, rough outlines are fine. For example, we knew we wanted to hit the local farmers market during our beach visit, so after breakfast one morning we meandered away to peruse and shop. We knew we wanted to go to the beach and at least hit the waves every day, so we did. Instead of cooking every night – without doing any serious meal planning – we opted to go out for dinner one night and have it delivered the next day.
We set overall goals for the day, but didn’t kill ourselves with it down to the potentially troublesome minute. It was so freeing. Sure, we’ll go to the beach, but maybe we’ll enjoy mimosas in the house first. Maybe we’ll have a Gabe happy hour before dinner, who knows where that’s going to be, or what it’s going to be? There is a lovely little shop in the town next door, maybe we should check it out sometime. Bottom line: nothing is urgent. We had ideas of what we wanted to do…but we did it and saw them at our own pace. It was as fulfilling and restorative as any other vacation I’ve taken. This is high praise from serial planners!
3. Consider your crew
this is a big problem. Of course, many of us can and do travel alone, and it’s a rich and wonderful experience where you can really set your own pace. However, if you’re on the road with a small group of friends , individuality needs to be considered for the best “go with the flow” experience. Our staff includes several planners (myself included!) who need extra encouragement from our friends to resist the urge to make such an arrangement. Thankfully, at their gentle, caring cries, we were able to actually pause. I am very grateful for this fact!
Personalities make a difference: that’s why traveling with friends is so great. But keep in mind that if you have some large schedulers on your team, you may need to support them to keep things going for a while. Don’t worry: you’ll get them there!
4. Enjoy hobbies
Many of us lead very busy lives: maybe we’re still working, or maybe we’re caring for a parent, child, or other family member. It can be hard to carve out time for yourself, and that includes time spent on beloved hobbies. So, to keep the holidays low-key, consider engaging in one of these activities that you don’t necessarily have time for.
Case in point: During our recent beach vacation, a friend brought her watercolors. She wanted to practice several new techniques, so every day she set up supplies, gave herself a quiet space to work, and drew. We marvel at her focus and focus, but she insists that it’s relaxing to be able to devote herself fully to her art.
Whether it’s taking time off for an unplanned jog or hike, jotting down notes or observations in your favorite journal, or sketching out your vacation surroundings, if you spend time on the road pursuing a favorite hobby, you’re likely to Slow down and focus.
5. Keep it simple
There are many ways to complicate a good vacation. You may feel the need to fill the time you spend away from your home or office with sightseeing, shopping, entertainment, and other activities. While these kinds of outings are great, trying to cram too many people in at once can actually damage your vacation, squeeze the schedule, and—often—put a little strain on the mix. If the intention of the holiday is to go with the flow, you don’t want that.
Advice: Keep it simple…although if you’re usually the busy type, that’s easier said than done. Pick your must-dos, but don’t rush to fix everything at once unless they’re on a specific timeline. Let things go and pop as you please. That’s when the good stuff will find you. A special conversation, a perfect sunset, or a resonant passage in a book you’ve been putting off—these are all examples of simple, indulgent pleasures that you might miss when you over-plan or plot.
6. Nothing is necessary except…
Last but not least, keep in mind that the most important part of “Surviving” Going with the Flow is a little perspective reset, nothing is really going on except doing your best to make sure everyone is having a good time necessary.
Again, I’m reminded of our recent outing to the beach. Our tour group was texting back and forth about a week before our departure. “What are you collecting?” a friend asked. “Should we plan a menu every day?” another chimed in. “Should I carry a bag?” a third wondered.
look? The planning has already begun and we are days away from actually hitting the beach. Full disclosure: I may be the main culprit.
We went back and forth until another wise woman in the text stream gently reminded us: “Nothing is necessary but sweatpants and sunscreen. Just throw something into a bag and here you go. We’ll all enjoy each other’s company and not have to worry about anyone else for a few days!
No truer words have ever been spoken, or in this case, texted. There’s no need to drive yourself crazy by over-processing travel. Staying in the moment, taking every opportunity and embracing the chill vibes turned out to be the perfect way to spend a few days with friends.
I know very well that this is not the way all my travels, trips and adventures are. When my family resumes international travel, I’ll definitely pull out guidebooks, stalk Google, and pack all the can’t-miss items each day. I’d probably plan to squeeze the most out of it every day.
But the trip taught me a valuable lesson: It’s okay to let it go once in a while. I’m so glad I gave it a try!

