10 Costly Mistakes to Avoid on a Warm Sunny Vacation This Winter

Judy Antell Avatar
Fruit snacks are an option for gluten and dairy free snacks for kids.

Going south for winter feels like a tonic to those us who reside in the frigid north. But people who are out of summer mode are likely to forget a few things when heading to Florida or a Caribbean island to relax on a beach in mid-winter. A little advance planning can help smooth the way and limit the damage — to your skin and your wallet.

These are the mistakes we’ve made so you don’t have to. You’re welcome.

1. Forgetting that Kids Grow. A lot. 

It always seems like a shock how fast kids can grow. And there is no more telling evidence of that than trying to squeeze a 5-year-old into his 4-year-old swimsuit — the one you bought extra big last year because you knew you would be going south for winter.

Do a test fit before you pack to make sure that swimsuit and those shorts from last year still fit. Nothing like wasting your time packing clothes no one can wear once you arrive.

If the summer gear doesn’t fit, pad the family holiday budget a bit to allow you to buy new online before you go. It will save you from wasting precious vacation time at the mall once you arrive.

2. Not Asking for What We Need

My mother, who lived in Florida, insisted that her skin was “used to” the sun, so she didn’t need sunscreen. That meant I had to:

A.) Check bags so I could carry my own more-than-three-ounce tube of sunscreen,
B.) Buy sunscreen when we arrived or,
C.) Ask my mom to pick some up for the grandkids so we could head straight to the pool when we arrive.

I learned after just one trip that asking Mom to buy some sunscreen is the answer.

Read More: The Best Sunscreens for Babies and Kids

3. Not Doing Our Homework

If you are visiting grandparents who live in a retirement home, check regulations on pool use, swim diapers, etc.  When my middle daughter was a toilet-trained toddler, a busybody at my mother’s adult community followed her around the pool, making sure she didn’t have an accident.

4. Wasting Precious Vacation Time

Pool floats at the Hilton Sandestin Beach Golf Resort & Spa in Miramar Beach FL
Bring inflatable floaties so you don’t have to waste vacation time and budget buying them when you arrive. Photo credit: Cindy Richards

Bring inflatable floaties and beach toys. These pack easily and you’ll want them at the beach or pool. If you forget them, you’ll be spending time (and vacation budget) buying them at the local tourist-gouging store.

Or, if you’re visiting Grandma, add that to her “buy before we arrive” shopping list.

Read More: How Grandparents Should Babyproof the House Before the Grandkids Come to Visit

5. Bringing Too Much

A host of companies rent everything a vacationing family needs. There’s no need to pack bulky items such as cribs and high chairs. Rent them instead, along with bicycles, bed guard rails, Razor scooters and plastic Little Tikes cars.

At least check the price on equipment rentals before you pack the trunk full of stuff you may not need. You’ll be happy you did if you have a flat tire on the road. No one wants to unpack the whole trunk to get to the spare.

6. Not Doing Enough Research Before Going South for Winter

This is especially important if you’re visiting family at seniors-only complexes. You’ll want to scope out local playgrounds so kids can run around and be loud without disturbing anyone.

7. Not Accounting for Local Norms

At home, you might eat early with your kids to avoid crowds. In Florida, you will want to eat late – after the early bird rush.

8. Not Bringing Warm Clothes 

At some point, your family holiday in the warm sunshine will end and you’ll have to return home. If you don’t want to do laundry on vacation, bring a clean cold weather outfit for the way home. We always see someone at JFK in January, shivering in shorts and a t-shirt.

Of course, you can wash the clothes you wore on the way south so they’re clean for the trip home. But we believe vacation means never having to say you did laundry.

9. Looking at the Calendar, not the Weather Reports

Just because it’s supposed to be warm in February wherever you’re going doesn’t mean it will be. Check the forecast so you’ll be prepared for cool temperatures, rainy days and other weather unpleasantries.

10. Not Expecting Bugs

No bugs to bug you is one of the highlights of a winter up north. But if you’re going south for the winter, plan for bugs. Bring insect repellent, or plan to buy it once you arrive.

Bonus Tip

With all of the extreme weather, raging fires and other unnatural phenomena, don’t make the mistake of not buying travel insurance.

Judy Antell is an empty-nester mother of 3 who spends a lot of time visiting her daughters. Why don’t they live in Brooklyn? Judy and her husband love to travel, by bike, car, or plane, whether to see their kids or have friend or couple adventures, mostly centered around vegetarian food.
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3 responses


  1. Thank you for the tips. I hope this year we will go on vacation, at least now I know what is important in preparation.

  2. very helpful. I always forgot to do the homework before the vacation 🙂 I will make a detailed plan next time.

  3. Thank you for the tips! I definitely got caught with the first one myself last trip. In no way you expect kids to grow that much and you don’t even notice it yourself because you see them every day, but when you try to fit last year’s or even a few months old clothes – just wow! They grow horrifyingly quickly. Also, please never forget the sunscreen! It is one of the most important things and people often forget completely about it until all of the family is pink or even bright-red from the sun!

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