Earlier this year, after returning from a trip, a friend made a comment that got us talking: “Joe, you always come back from vacations looking so well-rested. I, on the other hand, feel like I need a vacation from my vacation.” I couldn’t help but laugh because I used to feel exactly the same way—burned out, exhausted, and weighed down after some of our trips.
As we chatted, it became clear that my friend’s problem wasn’t just about his overloaded schedule on vacation—it was his tendency to overpack everything. And I’m not just talking about his suitcase. He was cramming his itinerary with more activities than he could handle, and the result was a vacation that felt like work. The truth is, many of us fall into the same trap, and it wasn’t until I learned to “unpack” a few things from my travel routine that I started coming home truly rested.
Overpacking Your Itinerary: Why More Isn’t Better
We’ve all done it—made the infamous overpacked itinerary. You know the one: breakfast at 8, city tour at 10, museum by noon, and don’t forget dinner reservations across town at 7. My friend confessed that he never left any room to actually enjoy where he was. And honestly, that used to be me too. I thought if I could tick off more boxes on my vacation checklist, it meant I was getting the most out of my trip. Spoiler alert: It didn’t.
Vacations aren’t supposed to be marathons. Overstuffing your itinerary is like overpacking a suitcase—you end up dragging a lot of extra weight for no reason. Instead, focus on the essentials. I shared with my friend one of the best lessons I learned from The Joy of Missing Out: “When we focus on everything, we focus on nothing.”
The key to a great vacation? Do less, enjoy more.
How to Avoid Overpacking Your Time
Just like packing your suitcase, think about your itinerary in layers. You wouldn’t throw in every piece of clothing you own, right? (Okay, maybe my friend would…) But when you’re deliberate about what you include, you only bring what’s most important. The same goes for travel plans. Prioritize the experiences that matter most, and give yourself space to truly enjoy them.
I told my friend about my new approach: pick one or two must-do activities for the day and leave the rest open. He looked at me like I was nuts at first, but once he thought about it, it made sense. If you try to do everything, you won’t enjoy anything.
Lesson 1: Build in Time to Unpack and Relax
When you overpack, you know that moment of dread when you have to unpack your suitcase and realize you didn’t need half the stuff you brought? The same feeling applies to vacations when you look back and wonder why you didn’t just take a nap by the pool or linger over a long lunch.
One of the biggest shifts for me came from learning to intentionally block out time to rest. I mentioned to my friend how I used to feel guilty for doing nothing. But Essentialism taught me that rest is essential—not just an option if there’s time. Just like you don’t pack three winter coats for a beach vacation, you shouldn’t pack every minute of your day with activities. Build in time to unwind, and you’ll come home feeling lighter.
Lesson 2: FOMO and the Overstuffed Suitcase
Let’s be honest: the real reason we overpack—whether it’s clothes or our schedules—is FOMO. We’re afraid we’ll miss out on something amazing. My friend admitted he feels this pressure to squeeze in every possible experience. I get it. I used to think that skipping something meant I wasn’t making the most of my trip.
But here’s the thing—just like you don’t need seven pairs of shoes for a weekend getaway, you don’t need to do everything to have a great time. In fact, some of my favorite moments have come from saying no to overstuffing my days and just enjoying what was right in front of me. I shared with my friend the liberating lesson from The Joy of Missing Out that it’s okay to miss things. You actually gain more by focusing on what truly matters.
Lesson 3: Reflect, Don’t Cram
One of the best tricks I’ve learned is to unpack as I go—both literally and mentally. When I’m on vacation, I take a few moments at the end of each day to reflect on what made it special. This way, I can savor the highlights and let go of any pressure to do more the next day.
I encouraged my friend to try this on his next trip. Instead of cramming his suitcase and schedule with “just in case” extras, I suggested he reflect on what truly brought him joy each day. It’s a simple way to extend the feeling of relaxation long after the vacation ends.
The “Unpack and Relax” Mindset at Home
My friend asked me how I manage to keep that refreshed, well-rested vibe after vacations. I explained that it’s all about bringing the vacation mindset home. Just like you shouldn’t overpack for a trip, you shouldn’t overload your daily life either. I’ve learned to simplify my routine, creating space for moments of rest and reflection. Whether it’s enjoying a quiet morning coffee or taking an afternoon walk, these little breaks keep me feeling recharged.
I suggested he do the same—finding ways to “unpack” his daily schedule, leaving room for rest and enjoyment. It’s a way to make sure that vacation glow lasts long after you unpack your suitcase.
The Takeaway
By the end of our conversation, my friend was ready to rethink how he plans his vacations (and his packing strategy). I’m hopeful that his next trip won’t leave him needing another vacation afterward. Overpacking—whether it’s your suitcase or your itinerary—adds unnecessary stress. The key is to keep things simple, focus on what matters, and leave room for rest.
So, the next time you plan a vacation, remember: don’t overpack your time or your suitcase. Sometimes, less truly is more. And who knows? You might just come back looking as well-rested as ever.