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What Are Your Winter Travel Plans?

By: Jen Shoop

Any great destinations on deck? We have some smaller local getaways here and there (hoping to take the kids skiing a few times this winter), but in terms of big travel, in 2026, we’re hoping to take our first international trip as a family, and in 2027, Landon and I have our sights set on Japan. I’m also hoping to squeeze a trip to London in somewhere in the next year. I’ve never been with Landon, which feels wrong. My sister lived there for several years and I deeply regret not staying with her for a stretch while she was there, but it was during a chaotic time in our life (babies, moving cities, selling a business and a home, trying to figure out New York City real estate market, etc.). Just another reminder to take the trip…!

What about you? What’s on your itinerary?

I also wanted to foreground two posts from the archives here: first, Magpie readers share their top tips for smooth travel days, and second, Magpie readers share their strategies for planning amazing vacations. We Magpies are highly strategic people; lots of incredible tips in the comments.

Now, a couple of travel finds for you. As an aside, I LOVE to gift travel gear. It’s such an exciting way to anticipate future memories and experiences (bonus points if you tuck in a travel itinerary or ticket!), and it’s not necessarily something you’d upgrade yourself. I can’t tell you how long I clung to the old, inherited, busted-at-the-seams suitcases from my parents’ garage. If it ain’t broke don’t fix it, but those were some shabby pieces — i.e., we “had a trick” to zipping it closed, one wheel didn’t work, etc.

fall + winter travel gear

BEIS ROLLER // LUGGAGE TAG // VINYL STICKERS // HEADPHONES // SAINT JANE TOILETRY KIT // BYREDO TRAVEL PERFUME // COMPRESSION SOCKS // HAND SANITIZERS // PASSPORT HOLDER

Even more finds below —

01. The Away carry-on .

02. Also, their Commuter backpack is so spacious.

03. My BEIS roller luggage (above), which I can’t travel without at this point. I love the Atlas Pink color.

04. This carryall bag from Dagne Dover.

05. This toiletry bag set.

06. These are the best travel size capsules for toiletries.

07. Travel day set.

08. Family passport holder. Genius!

09. Refillable hand sanitizers.

10. Really great quality headphones.

11. MagSafe battery pack from my favorite — Velvet Caviar.

12. Essentials from Saint Jane.

13. Mini toiletry set.

14. One of my favorite travel perfumes.

15. Puffer from Athleta.

16. Compression socks.

17. This expandable suitcase.

18. Chic luggage tag.

19. Kids backpack.

20. Kids carry-on in cute colorways.

21. These stickers for identifying luggage, water bottles, etc. (10% off with MAGPIE10)

22. Custom luggage tags.

Travel Day Style.

(Layering is key for me — )

fall + winter travel gear

HEADPHONES // CLOGS // CARRY-ON // TOTE // UTILITY PANTS // LONG SLEEVE // CARDIGAN // HAND SANITIZERS

fall + winter travel gear

SWEATPANT JEANS // TURTLENECK // COAT // BACKPACK // SNEAKERS // PASSPORT HOLDER // COMPRESSION SOCKS // SAINT JANE TOILETRIES // PERFUME

My Travel Toiletry Favorites.

Travel toiletry favorites collage

TRAVEL CAPSULES // SAINT JANE TOILETRIES // EYE SERUM // PERFUME // TOOTHBRUSH // FACE WIPES // EYE MASKS

P.S. Styling vests for fall.

P.P.S. Are you friends with your parents?

P.P.P.S. On sounding like yourself.

+Shop all of my recommended products + Magpie promo codes.

This post may contain affiliate links. If you make a purchase through the links below, I may receive compensation.

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Kelly
Kelly
4 months ago

Christmas we stay put and mostly expect guests. Monaco is low key the most magical Christmas market.

Our spring will include 2 trips to Paris with kids for necessary paperwork, and it’s my first time! Possible trip to Norway on the horizon depending what my SIL decides for her 40th. Hoping to take a camping trip during the Grand Prix and avoid the craziness. And I’d like a trip to Ireland every August to become a new tradition! I like the idea of going back to a place and building memories there, and my SIL is there a few years.We also don’t have any US trips currently, we will see if I do a solo trip to see my nana or if we do one with this kids and all.

Claire
Claire
4 months ago

We are hoping to do Japan next year as well! Spain this spring break. You are amazing to take the kids to Europe this year, I first took mine to Paris when aged 8 and 10- it went well! Lots of Jet lag but we had a wonderful time and they were old enough to remember the trip

Iris
Iris
4 months ago

Funny— we just did a trip to London this past summer and we’re headed to Korea and Japan over the holidays! We had so much fun with our daughter (she’s 4) in London and we go to roughly once a year to see family. Happy to provide recs if/when you need them 🙂

Emma
Emma
4 months ago

I have a family ski trip in February and lots of smaller trips scattered around 2026. I’m also hoping to get to London, we’ll see how it goes!

On the topic of said ski trip, it’s been years since I lived somewhere/had the ability to ski often and my ski gear is woeful. My helmet and goggles are thankfully still kicking but I am in need of a new jacket and pants, Do you have any recommendations beyond the usual Patagonia/North Face/Spyder etc.? I am hoping this gives me the push to start going move often even if it’s just on my own for the day.

Shauna
Shauna
4 months ago
Reply to  Emma

Helly Hansen is great. Marmot and Arcteryx too!

Emma
Emma
4 months ago
Reply to  Jen Shoop

Thank you so much! This is SO helpful!

Alicia
Alicia
4 months ago

My husband and I leave to Japan on Thanksgiving Day. The two of us are then spending Christmas in San Diego. London is one of my favorite cities in the world – I would go back over and over.

We find long weekends (president’s day, etc.) to spend with family and other weekends for some family who is closer. That way while my sister and other family members are in our 40’s we can use some of these longer holidays to do things we want like longer trips to Europe/Asia. Doesn’t work for everyone, but its worked for us for a long time! Everyone once-in-a-while we all do something together (like a family trip to Belgium a few years ago over Thanksgiving), but no one is pressured.

Madeleine
Madeleine
4 months ago

Hi Jen! Random but do you have a favorite corduroy pant? Thinking about putting a pair on my wishlist xx

Madeleine
Madeleine
4 months ago
Reply to  Jen Shoop

Thank you so much!!

Anita
Anita
4 months ago

We are going to Florida for a wedding in December. I am thrilled because I have never actually seen Florida. My mom grew up in the Caribbean, so I have been through Miami airport so many times to see my family, but never actually done anything other than the occasional overnight stay in a hotel between flights.

But I do need tips for flying with morning sickness. I am hoping that it will be less by then, but I am nervous about six hours stuck in a plane with my heightened sense of smell. Any tips?

Jennie
Jennie
4 months ago
Reply to  Anita

Anita, I traveled while super sick from pregnancy, and my biggest tip would be: wear a mask, both because you absolutely don’t want to get sick because you can’t take any of the good meds AND because it can reduce some smells/give a sense of control of smells. Bringing a little essential oil in a smell that helps the nausea was helpful—I could dab a teensy bit on the mask and that helped me a lot! This is def something to try out before you are on the plane, though—gotta make sure the scent works for you, etc.

Bringing your own little snacks that you can keep down is also necessary! Can’t rely on the airport or the plane.

And also let the flight attendants know you are pregnant and not feeling well! People are kind, and they will do what they can to help you (ginger ale? Tea? A smile?)

Sending you good travel and pregnancy vibes!

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