15 Travel Essentials for Multi-generational Trips

I’ve been traveling with my mom and sisters before I was born. When my mom was eight months pregnant with me, our family moved from the U.S. to the U.K. Since my mom was too pregnant to fly, she hopped on Cunard’s Queen Elizabeth II for the transatlantic crossing, bringing along my three sisters, who were all under the age of 10. 

We spent our childhoods crammed in the back of a car as we road-tripped through Europe to go skiing in the winter, or flew back to the States to spend summers at my grandmother’s house near the Jersey Shore. Now, as adults, my mom and my sisters are still my favorite travel companions. We don’t live near each other, so we’re just as likely to meet up for a vacation at my mom’s house in Idaho as we are to rendezvous in Porto, Palawan, or Provence. 

In our lifetime of traveling together, we’ve perfected the art of packing. Below, you’ll find the 15 travel essentials we rely on for successful multi-generational trips. From versatile travel clothes and UPF-protective accessories to useful gadgets, these must-haves keep us safe and comfortable wherever we go together.

Hiking Shoes

On trips with my mom and sisters, our main objective is usually to go on a really long walk, whether that means traipsing 30,000 steps through Paris or hiking in Montana. Everyone in my family (except for me) owns a pair of Hokas and they talk about them as if they’re the holy grail of shoes. I have yet to join the club, but I have to admit I’m Hoka-curious, especially seeing how easily my mom can zoom up hills — even after a hip replacement. She owns a neon-accented pair of high-tops, but I think I’d probably go with a more basic style like the Hoka Transport Shoes, which would easily pass for everyday sneakers in a pinch. 

A Versatile Black Dress

You never know where the night will take you, so it’s important to travel with something nice enough to wear to a Michelin-starred restaurant or a cocktail bar at a fancy hotel. It’s easier to dress something up with jewelry and a shawl than to pack a formal gown, so we’re all fans of the versatile black dress. My mom’s favorite is one she bought at Anthropologie years ago, and my sister, Monica, has a simple black sheath dress (similar to this satiny, almost-sold-out, V-neck frock from Madewell) that works as both a beach-appropriate bathing suit cover-up and an elegant evening dress. 

This silk dress from Quince is a travel staple for my sister, Abby. The lightweight, washable, stretch-silk fabric ensures it packs up small (it looks good with a few wrinkles, don’t worry). You can wear it for a day of sightseeing with a pair of sneakers or dress it up with heels and earrings for an event or dinner out (she’s even worn it to a destination wedding). 

Comfy Travel Pants 

All of us have been served targeted ads for Ripley Rader pants on Instagram, but I was the first to cave. I now own them in multiple colors and, while I’m embarrassed to have spent nearly $200 on a pair of lounge pants, I have yet to find a better alternative (and now, I’ve turned my whole family onto them). The wide-leg pants are universally flattering and fit the bill for a comfortable travel look that’s still polished and put together, especially when paired with a button-down. If you can’t justify the price tag, check out these Adrianna Papell lookalikes at Amazon; they’re on sale for $33.  

A Packable Down Jacket

I live in New York, my mom lives in Idaho, and two of my sisters live in Montana. Unless we’re going on a ski trip, we usually travel somewhere warmer than home, especially in the winter. But, that doesn’t mean that outerwear isn’t at the top of our packing lists. We all travel with a packable down jacket that’s cozy enough to keep us toasty during the commute to the airport, but lightweight enough to stuff into a pouch for the duration of the trip. My mom’s favorite travel jacket is from Stio, and my sister Abby and I love our puffers from Uniqlo — though, I have my eye on this colorful option from Cotopaxi.

Lightweight Cashmere Sweater

One thing I never knew about cashmere until the material is that it’s warmer than it looks — almost too warm sometimes. This makes it a convenient travel staple since you get an extra-warm layer without wasting space in your suitcase on a heavy jacket. On nearly every trip, my mom can be counted on to have her trusty navy blue cashmere sweater in her bag, similar to this affordable cashmere crewneck from Everlane. But, if you’re shopping on a budget, there’s a wallet-friendly version of the classic sweater at Quince that’s just $50. 

A Packable Hat

My mom’s signature travel accessory is this packable hat (in royal blue) from Scala. It has a UPF 50 rating so you can get away without putting on sunscreen when you’re feeling lazy. Though I wasn’t a fan of the style when my mom first started rocking it, I have to admit that I’ve been influenced; I keep considering getting one just because it’s so easy to pack and does a great job of protecting your skin.  

A Steamer

My mom is weirdly obsessed with ironing. If we get to a hotel or rental with an ironing board, she will iron all of the clothes in her suitcase, even if we’re packing up and leaving the next day. Whether or not a hotel room has an ironing board is a make-or-break criterion for her. Oddly, I don’t even own an iron or ironing board at home, so this is not a trait I inherited. Since she can’t travel with her own ironing board, the next best thing is a top-of-the-line portable steamer from Steamery. Similarly, the Bear Steamer, which is $40 at Amazon, will get those pesky wrinkles out of your favorite travel clothes fast. 

A Water Bottle

A trait I did inherit is that I’m incredibly picky about the taste of my drinking water. My main reason for having the Delta credit card is that I prefer to fill up my water bottle there instead of the crusty-looking water fountains in JFK airport. I have a LifeStraw water bottle for camping, but my sister, Abby, brings hers everywhere since it can make any tap water taste good with its filtered straw. The double-wall insulated bottle filters bacteria, parasites, microplastics, sand, dirt, and cloudiness in two stages to ensure clean, safe water.  

Sunscreen

I can’t remember which of us first started using Elta MD sunscreen (or whose dermatologists recommended they try it), but now we’re all fans of the tinted mineral sunscreen and bring it on every trip. It’s lightweight and offers mostly sheer coverage, and I’ll even use it in the evenings instead of makeup. I also have the waterproof version for beach vacations, which is a bit thicker and stickier, but stays on for hours. 

Jewelry Case

My sister, Carly, wears a lot of big jewelry pieces, and one of her favorite travel accessories is a sturdy jewelry case similar to this one from Dagne Dover, which holds all of her bangle bracelets and dangly earrings and protects them from getting bent out of shape. Side note: My mom is no longer allowed to travel with jewelry because she’s left her jewelry case in the hotel too many times.

A Sleek Crossbody Purse

While Monica and I have been known to use a fanny pack in our travels, Abby absolutely refuses to. Instead, she prefers a slim crossbody bag similar to these options from Cuyana or Madewell that are just big enough to hold a phone, a wallet, and a passport (and small enough that the nicer flight attendants don’t count it as a dreaded “third item” when boarding). 

A Travel Backpack 

My sisters all have kids of their own now and have realized how important it is to be able to travel hands-free with a backpack instead of a tote bag. My sister, Carly, has one similar to Lululemon’s Wanderlust Backpack (which has now become a travel staple of mine). It holds everything you need for the plane and fits nicely under the airplane seat, making it ideal for long journeys. 

A Space-saving Toiletry Kit

Carly also swears by her Cadence travel container set for everything from face serum to vitamins. The multi-use leakproof canisters come in various sizes and fit together via magnets, and they don’t take up any precious real estate in a suitcase or personal bag. 

A Travel Pillow and Blanket

We grew up flying back and forth to Europe, so we’ve all mastered the art of staying comfortable on long-haul flights. My sister, Abby, and her three-year-old daughter (who has already been to eight countries) never fly without this ultralight travel pillow and a packable down blanket. The pillow is technically for backpacking, but it works great for the plane and weighs just 2.1 ounces. 

Travel Games and Entertainment

Books are an essential part of our travels. We’ve started an informal sort of book club where we plan to read the same novel before the trip so we can talk about it. But we’re firmly divided when it comes to our reading formats. My mom and Monica are Kindle people, while the rest of us prefer paperback books. We’ve also never traveled without a deck of cards and, conveniently, our favorite card game, Oh Hell, requires five players. We also love a good game of Backgammon, which tends to involve less back-stabbing and spiteful grudges than Oh Hell — overall, it’s a safer option for already hectic travel days. 

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