Should I Pack That? 6 Questions to Ask Yourself First

Going on vacation is almost always a guaranteed good time. But packing for said vacation? Not so much fun. There are so many decisions to be made, from selecting the appropriate suitcase to settling on the right clothes for your destination and designated activities (not to mention fitting everything you need in a suitcase), it’s no surprise if you’re totally overwhelmed. Luckily, we can turn to travel professionals not only for help with booking our trips and vacations but also for assistance in the packing department.

We asked a few exploratory gurus to share the questions they recommend their clients ask before leaving for the train station or airport.

1. How many days will I be away?

The amount of time you’ll be away from home will determine the number of outfits and products you’ll need to pack. “On my packing list document, I indicate the number of outfits needed for each person, and then I add a couple of extra outfits for the kids,” says Jennifer Turner, Georgia-based Disney travel agent. “This is especially helpful for parents, as they’re not only packing for themselves but also the kiddos!”

2. What documents will I need for travel?

Of course, if you’re traveling out of the country, you’ll need a passport, but no matter how close to home you’re going, you’ll also need your driver’s license. Additional documents Turner recommends including are your itinerary, insurance cards, hotel confirmations and transportation confirmations.

3. Do I have all the charging cables I’ll need?

Turner learned this lesson the hard way when her phone kept dying midday at Disney because she didn’t have a portable charger. Now, this is an essential item for her to pack—and she tells her clients to do the same. Additionally, don’t forget regular phone and iPad chargers as well as any adapters for international destinations.

4. Do these clothes and shoes go with multiple outfits?

Jennifer Jacob, CEO and founder of Explorateur Travel, LLC., makes sure to ask the question of whether or not she can wear an outfit day and night, as well as if she can mix and match pieces to create different outfits. “If an item can only be worn for one specific instance (unless a wedding or an event), I lean towards leaving it out,” she says. “However, if I can throw on a different jacket, a different shoe and new jewelry and transition the outfit into a new look, I feel confident that it should make the trip.”

5. Do I feel comfortable and confident in what I’m packing?

It might be tempting to pack all of the new clothes you’ve purchased that still have their tags, but Jacob reminds clients that the last thing you’ll want to wear on vacation is something stiff and uncomfortable. “In the past, I spent so much time and money on packing my suitcase full of things that seemed like they would be cute in pictures, or things that I wanted to look good in, but I couldn’t enjoy myself because I felt self-conscious,” she explains. “I’ve learned over time that feeling confident is much more attractive than anything that you can wear.” Bottom line: Focus on styles that you know you will feel great in.

6. How much room does this take up?

Jackets, boots, wedges… they all take up a lot of room. “Unless I know that I will wear something more than once, or that I can wear it on the plane (I wear the bulkiest items to save space), I try to leave it at home,” says Jacob. “Denim also takes a lot of space, so simple dresses get favored a lot.” Her go-to for packing is “one-item outfits,” like maxi dresses.

 

Jenn Sinrich is an editor in New York City, a self-proclaimed foodie always looking for the healthier version of all recipes, a passionate lover of all things cheese, a friendly New Yorker, Bostonian at heart and proud Red Sox fan. Love cats? Cheese? Mac n' Cheese? Follow her on Twitter and Instagram.