Dear Annie: When vacation feels like work

Published On: August 18, 2025

TO ANNIE: Every summer, I organize a vacation. I see my family laughing together, with beverages in hand, toes in the sand, on a serene beach. But what’s the truth? Complete chaos.

Even though I arrange the travel, locate the rental, ensure that everyone has sunscreen, passports, food, chargers, and swimwear, I still am held accountable when something goes wrong. My youngest usually seems to get sick as soon as we get there, my teen pouts because the Wi-Fi is slow, and my spouse gripes about the price. We didn’t spend as much time unwinding last year as we did debating over where to eat. Not to mention the incessant packing and unpacking, delayed flights, and airport meltdowns.

I’m more worn out by the time we arrive home than I was before we left, and I typically require a vacation to recuperate.

Is it possible to make summer travel more pleasurable and less stressful? Or should I embrace the staycation lifestyle and give up on the ideal family vacation? — Overwhelmed and Overpacked

DEAR OVERWHELMED: You’re not by yourself. When actual people with actual needs, feelings, and opinions begin to move through airports and strange hotel rooms, the ideal of the ideal family holiday frequently vanishes.

You seem to have taken on the responsibilities of packing expert, travel director, and emotional manager all at once, which leaves little time for you to truly enjoy the vacation. Letting go of the need for perfection is one of the best strategies to reduce travel-related stress. Instead, strive for adequate and schedule downtime for yourself.

Assign work. Give your teen an engaging project to research. Let your significant other handle the logistics or organize a meal. Select more leisure time and fewer activity. Take a deep breath, laugh when you can, and keep in mind that even the nasty bits can become cherished family tales if things go awry, which they most likely will.

For a vacation to have purpose, it doesn’t have to be perfect. Mistakes can occasionally create memories.

For Annie Lane, send inquiries to [email protected].