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The Essentials: Multi-destination vacations

Tote along everything you need, for every stop

Ariel Kanter
By Ariel KanterAug 1, 2022 3 minutes read
Woman organizing open luggage filled with items ready to go on vacation.
Image: Getty Images

After more than two years of travel restrictions, far-flung vacations suddenly seem very—well, involved. And many travelers feel that if they’re to board a plane, the effort needs to be “worth it.” Enter the multi-destination vacation, which hits several places in one go and often promises a rewarding, enriching mix of cities and countrysides, beaches and mountains, and everything in between.

But packing for these trips can be tricky, especially if you’ll be gone for a while, criss-crossing climate zones and partaking in an assortment of activities. Below, a curated list of packing essentials.

Away F.A.R. Convertible Backpack 45L
Vans Classic Sneaker
Girlfriend Collective Black Compressive High-Rise Legging
Jonathan Adler 2-in-1 Travel Game Set
From left to right: Away F.A.R. Convertible Backpack 45L, Vans Classic Sneaker, Girlfriend Collective Black Compressive High-Rise Legging, and the Jonathan Adler 2-in-1 Travel Game Set

Away F.A.R. Convertible Backpack 45L

Buy now: $220, awaytravel.com

Made from recycled materials, Away’s 45L convertible backpack fits a carry-on’s worth of stuff. Removable padded straps take it from a backpack to a duffel bag in seconds; dual compression systems help you pack more in less space; and exterior pockets keep your devices organized.

Vans Classic Sneaker

Buy now: $60, nordstrom.com

Shoes take up a lot of luggage real estate, so bring a pair that does double duty, like the Classic Sneaker from Vans. They’re comfortable, they look cute when dressed up or down, and they're lightweight enough to keep your feet cool in hot climates.

Girlfriend Collective Black Compressive High-Rise Legging

Buy now: $78, girlfriend.com

Wear Girlfriend Collective’s compressive, ultra high-rise leggings on the plane, then wear them again for anything active you have planned on your vacation. Made from recycled plastic bottles, they’re sweat wicking and squat proof, feature a hidden back pocket for keys or cards, and come in black for ultimate versatility.

Jonathan Adler 2-in-1 Travel Game Set

Buy now: $25, galison.com

Containing both backgammon and checkers, this handsome game set will help you pass the time on travel days. It’s also beautifully designed and perfectly practical, with wood pieces and a hinged, double-drawer construction.

Herschel Fifteen Hip Pack
Everlane Linen Picnic Jumpsuit
Uniqlo Supima Cotton Crew Neck Short Sleeve T-shirt
Reformation Classic Crew Sweatshirt
From left to right: Herschel Fifteen Hip Pack, Uniqlo Supima Cotton Crew Neck Short Sleeve T-shirt, Reformation Classic Crew Sweatshirt

Herschel Fifteen Hip Pack

Buy now: $32, herschel.com

Keep your belongings close with Herschel’s signature fanny pack. Use the adjustable, clip-fasten strap to wear it around your waist or over your shoulder, and you'll never worry about leaving it behind.

Everlane Linen Picnic Jumpsuit

Buy now: $110, everlane.com

Made from soft, breathable linen, this jumpsuit with a removable belt is a dress-up, dress-down piece. The square neckline and cropped straight leg are flattering, while the adjustable (and bra-friendly) straps and elasticized back ensure comfort no matter where you’re headed.

Uniqlo Supima Cotton Crew Neck Short Sleeve T-shirt

Buy now: $15, uniqlo.com

Great on its own or layered, Uniqlo’s basic tee will be the workhouse of your vacation wardrobe. It’s made from Supima cotton for a soft, elegant feel and features a basic cut that goes well with a variety of bottoms.

Reformation Classic Crew Sweatshirt

Buy now: $68, thereformation.com

Stylish but cozy, Reformation’s crewneck sweatshirt works just as well on the plane as it does over a sundress on chillier evenings. Details include ribbed detailing on the neckline, cuffs, and hem, plus a comfy, roomy fit.

Ray-Ban Wayfarer Folding Classic sunglasses
Ampere Tech Unravel Wireless Charger
Ray-Ban Wayfarer Folding Classic sunglasses (L), Ampere Tech Unravel Wireless Charger (R)

Ray-Ban Wayfarer Folding Classic Sunglasses

Buy now: $114, ray-ban.com

A perfect space-saving option, these Ray-Bans fold up when not in use, but still sport a highly durable frame. Modeled after the brand’s Original Wayfarer Classic, they’re always in style and can be fitted with prescription lenses.

Ampere Tech Unravel Wireless Charger

Buy now: $69, ampere.shop

Keep your devices at full battery while on the go with the Unravel wireless charger. It folds up into a one-inch stack, can charge three devices at once, and features a patented double hinge so you can use it in multiple orientations, including as a charging stand.

Kangora Plain 100% Cotton Adjustable Baseball Cap
Pack-It Essentials Cube Set
Master Lock 4688D Luggage Lock
Andie Tulum Ribbed Swimsuit
From left to right: Kangora Plain 100% Cotton Adjustable Baseball Cap, Pack-It Essentials Cube Set, Master Lock 4688D Luggage Lock, Andie Tulum Ribbed Swimsuit

Kangora Plain 100% Cotton Adjustable Baseball Cap

Buy now: $9, amazon.com

Sun hats are fun, but they hog a ton of space in your bag. Instead, bring this simple, one-size-fits-all baseball cap, which comes in a range of fun colors and has a pre-curved bill so you won’t end up bending it too much.

Pack-It Essentials cube set

Buy now: $55, eaglecreek.com

Keep your luggage organized with Pack-It’s Essentials cube set, which includes an antimicrobial shoe organizer, a medium-sized cube to store dirty clothes, and a small compressor cube to maximize space. The packing cubes will help you remember what you brought and stay tidy no matter how many stops you've planned.

Master Lock 4688D Luggage Lock

Buy now: $10, amazon.com

If you have a long layover and plan to leave the airport in between flights, store your luggage in a locker with this TSA-approved lock. You can also put it directly on your luggage—it can be unlocked and relocked without the risk of being damaged by security screeners.

Andie Tulum Ribbed Swimsuit

Buy now: $115, andieswim.com

Pack a swimsuit designed for all sorts of activities, like Andie’s cult-favorite Tulum one-piece. It provides plenty of coverage and looks chic, thanks to criss-crossed straps and a ribbed texture.

Go-to gear for going new places
Ariel Kanter
Ariel Kanter is a freelance writer and editor with over a decade of experience covering food, travel, and fashion. Her work can be found in The New York Times, Vanity Fair, New York Magazine, Serious Eats, Resy, Afar, and more. For the latest, follow her on Instagram @ArielKanter and subscribe to her newsletter.