How-to: Pack a Carry-On for Two Weeks

If you’re a frequent flier, you know what a hassle it can be getting from one destination to the next. Between long lines at check-in and security to hopping terminals for connecting flights, it would be a miracle to travel without delays. One of the biggest pains of travel is checking luggage — no one wants to pay a $25 fee, just for their luggage to be lost. We can all agree that the last thing you want is to arrive in Europe and not receive your luggage for three more days. Case in point — we always try to fly with just a carry-on, when possible. We know what you’re thinking, “my trip is way too long to only pack a carry-on,” — but that’s where we come in. With the right tools and a savvy strategy, you can pack two weeks in a carry-on.

Don’t believe us? We’ll prove it. Our Digital Designer, Amanda, recently went on a two-week trip to Argentina. In just one carry-on and one personal item, she successfully packed 14 days’ worth of clothing, accessories and necessities. Here’s how she did it.

Luggage Essentials

22” Rolling Luggage

Weekender Travel Bag

PRO TIP: By using rolling luggage as your carry-on and a large travel bag as your personal item, you’re essentially able to fill two carry-ons, making this possible. The Weekender is perfect for the things you’ll need easy access to on the flight — laptop, travel documents, snacks, and ear buds (plus anything that doesn’t fit in your rolling luggage). This is also where you’ll stash your handbag (AKA, your usual personal item) while going through security.

Organization Heroes

• 3 Packing Cubes — 1 Small, 1 Medium, 1 Large
Keep your clothing compressed for maximum packing space

Hanging Travel Organizer
Perfect for keeping toiletries and jewelry neat and separated

Ditty Bag
Great for separating worn undergarments from unworn

Slim Travel Organizer
Travel documents will stay neat and safe with RFID technology

PRO TIP: It may seem like these extra items just take up more room, but you wouldn’t believe how much space they save! Packing cubes can easily compress and make your clothing more compact.

Packing List


8 dresses
2 pairs of jeans or shorts
3 cardigans
3 shirts
1 pair of pajamas
extra undergarments
2 bathing suits
1 pair of sandals
1 pair of wedges
1 pair of sneakers

PRO TIP: Whether you’re staying at an Airbnb or a hotel, you’re likely to have access to a washing machine at some point during your trip. USE THIS! You’ll want to be able to re-wear your tops, bottoms and dresses more than once. Try to plan your clothing to all be in the same color palette; it will make mixing and matching so much easier!


Carson Saddle Bag
other jewelry

PRO TIP: Wear your sneakers, hat and heaviest clothing on your travel day to save space in your luggage.


hair straightener
bobby pins
carry-on compliant shampoo, conditioner, body wash, toothpaste
powdered laundry soap
additional necessities

PRO TIP: Use the Hanging Travel Organizer to keep your toiletries neat.

Travel Accessories

travel documents
phone charger
ear buds
laptop and charger
irst aid: Dramamine, ibuprofen, band-aids, etc.

PRO TIP: If there is one thing you can’t forget, it’s an adapter! When you’re traveling to foreign countries, the outlets will likely not fit your iPhone charger. Order an adapter online ahead of time to save yourself the trouble.

Shop Travel


Leave a comment below or read what others wrote (3).

  1. Kaenhu said on :

    I have traveled with only carry-ons for 8 years and I have taught my kids to do the same. It is a shocking sight when we have arrived as a family with 4 kids and the only person with checked luggage is my husband. We have gone for 3 weeks to Africa, Vietnam, several countries in South America and Europe and even skiing trips with each person taking only carry ons. I can’t imagine doing it any other way now. I do all the things listed in this article! I would also like to add taking along clothing that dries fast in the event that you do have to wash (or at least rinse) your clothes in a hotel sink. Loved this article and VB travel bags in general!

  2. Tips for Spring Break: Travel Like a Pro - Vera Bradley Blog said on :

    […] you’re planning a long vacation, see how to pack a carry-on for a two-week trip and use our handy packing checklist. Wondering what bag is best for your trip? Take our travel quiz […]

  3. Lorraine said on :

    I personally do not like Vera Bradley at all!!!!!!!! Good luck!

Fill out your details below to submit your comment. Your name will be displayed, but not your email address.