Hey friend,
I just got back from a family vacation to Jamaica — and it was amazing. Two of my teenagers came along, and we went zip-lining, horseback riding in the ocean, swam with dolphins, and even tried snooba diving (which I now know is not my jam… I’m good with being on top of the water, thanks! 😂).
But here's what made this vacation different than ones we used to take…
It wasn’t stressful.
It wasn’t filled with guilt.
It was actually fun — all the way through.
Years ago, vacations looked very different. My husband and I would “discuss” what we could afford while we were already on the trip.
We’d go back and forth on how much was going on the credit card, if we could really afford it, and whether we should just “screw it” and figure it out later.
And that led to what I call the vacation guilt hangover.
Now?
We plan ahead.
We prepay for excursions.
We budget for the fun and give ourselves a spending buffer.
And let me tell you: We enjoy things SO much more now that we know the money part is taken care of.
🧳 So here are 6 sneaky money stressors that creep into vacations — and how to avoid them:
1. “We’ll Figure It Out Later” Thinking
Sounds fun in theory. But this thinking creates future stress. You deserve better than that!
→ Plan what you want ahead of time and budget for it on purpose.
2. Swiping Without Talking It Through
This one used to get us! One of us would say “YOLO,” the other would freeze up.
→ Avoid the tension by setting a spending plan together before you go.
3. Guilt That Steals the Joy
You shouldn’t be thinking about interest rates during a dolphin swim. 😅
→ Prepay what you can so you’re mentally free to enjoy the moment.
4. Unexpected Fees & Hidden Costs
Resort fees. Baggage charges. Tips. Snacks. All the extras add up fast.
→ Build a 10–20% buffer in your travel budget just for this reason.
5. Kids + Teens Asking for Everything
Gift shops, extra snacks, random purchases… it’s constant.
→ Give them their own spending amount and let them manage it.
6. Loss of Income While You’re Away
If you're self-employed or don’t have PTO, that time off costs more than the trip.
→ Pre-save for both the vacation and any missed income.
🛫 Want a Vacation With No Guilt Hangover?
It’s totally possible — and 100% worth the effort.
You can plan a trip that feels fun and financially free.
If you want a head start, I made a quick freebie for you:
👉 [Download: The Stress-Free Vacation Budgeting Checklist]
Your next vacation can be full of peace — not financial pressure. Let me help you make it happen.
Cheering for you,
Jenny Cioto
💛 Stingray-dodger, budget boss, vacation freedom fighter
See you next week!
