Holiday Travel Tips and a Winter Travel Outfit

Hello, friends. Happy Monday! Today I’m excited to partner with AIG Travel to share my best holiday travel tips and the perfect winter travel outfit.

The perfect winter travel outfit!

I can’t believe I’m saying this, but the holidays are fast approaching, and it’s time to start planning! For many of us, that means planning recipes and menu plans, starting holiday baking, decorating, buying presents, and making holiday travel plans.

My Top 5 Holiday Travel Tips

We often travel over the holidays to visit family, and it definitely takes more preparation and creativity to travel at holiday time than other time of year. I’ve learned a lot through trial and error over the years so here are some of my best holiday travel tips.

#1. Pack efficiently with outfits that mix and match. In the summertime, I’m always happy to throw in one more outfit or one more pair of shoes “just in case,” but in the wintertime, I try to pack as efficiently as possible because winter clothing and outerwear is so bulky. After all, no one wants to be loaded down like a pack mule on vacation!

Holiday Travel Tips

I recently watched a fellow blogger as she traveled Europe, and she packed almost everything in shades of black, grey, and camel. Everything went together, and she always looked put together without being redundant. It was quite impressive!

Holiday Travel Tips

#2. To save room in your suitcase, wear your heaviest clothing en route. Sometimes I wear my coat and carry it on the plane with me, and other times I stash it in my suitcase when I get to the airport, but I always wear my heaviest shoes which are usually tall boots. I also like to have a big blanket scarf because I can wrap it around me to stay warm in the car or the plane, and I always feel chic and put together, even if everything else I’m wearing is casual.

Another great item to have is a packable coat. Packable coats are lightweight so they don’t add extra weight to your luggage, AND they compress so they don’t take up much space in your suitcase. Get one with a hood, and it will double as a rain coat. This is a great example of a winter travel outfit.

Holiday Travel Tips and the Perfect Winter Travel Outfit

Holiday Travel Tips and the Perfect Winter Travel Outfit

Holiday Travel Tips and the Perfect Winter Travel Outfit

Holiday Travel Tips and the Perfect Winter Travel Outfit

similar scarves // similar coat (plus size option) // jeans // similar boots // tote // suitcase // sunnies

#3. Mail presents and other oversized items to your destination ahead of time. The hardest thing about traveling for the holidays is transporting presents. Not only does it make playing Santa difficult (I’ve had to come up with more than one creative excuse when the kids discovered a present hidden in the trunk of the car…) but it’s extra baggage that can be hard to fit in your suitcase or the trunk of the car. Even if you’re not flying to your destination, shipping the bulk of your presents ahead makes the trip much less stressful.

Holiday Travel Tips and the Perfect Winter Travel Outfit

#4. Consider purchasing travel insurance such as Travel GuardOne thing a lot of travelers don’t readily think about is protecting their vacation. We spend considerable time and money to plan a holiday travel experience, so I want to make sure to protect my investment in case of winter storms or other unexpected events. A moderately-priced travel insurance policy can help with the costs of unforeseen trip delays or cancellations, lost or damaged luggage, and medical emergencies while traveling. Of course no one wants to think of what might wrong on their trip, but if something does, it’s nice to know you have protection.

Two years ago, we took a family trip to Arizona, and my son came down with the flu. We had to cancel all plans and stay put while he recovered. Fortunately we were able to secure a hotel room for the duration of our time there and use our return flights, but if anyone else had gotten sick, we would have had to change our plans and we could have lost considerable money on the hotel and return flights. Most. Stressful. Vacation. Ever. I’m grateful it worked out, but having travel insurance would have provided much needed peace of mind.

Another example of a time we could have used travel insurance is last year when we bought plane tickets to Maine to visit family after Christmas and our flights were cancelled due to winter weather. You just never know what’s going to happen when you travel, so the best practice is to plan for the worst and hope for the best. Travel insurance can provide assistance with navigating canceled flights, lost bags, sudden health emergencies, and more.

AIG Travel’s Travel Guard insurance solutions include global travel assistance, emergency medical services, and even concierge services to help you with whatever you need, whenever you need it. To learn more, visit or call 1.800.826.4919.

#5. Be patient and get creative when necessary. Traveling for the holidays is extra stressful because so many people are doing the same thing. Airports are often crowded, highways are likely jammed, and everyone is cranky and anxious to get to their final destination and pour a glass of eggnog! Do your research and avoid peak travel dates — especially with air travel. This can save you money as well.

If you’re driving, leave extra early or late in the day. We’ve been known to drive through the night to avoid crazy daytime traffic on busy holidays. Be prepared to detour if the GPS warns you of a traffic backup ahead, or take an extra day and explore a new area on the way. Pack plenty of snacks, and if you’re flying, eat before you get on the plane. Make sure you have medications and all the necessities in your carryon in case of lost luggage.

Most importantly, pack your sense of humor. It will make the trip so much more pleasant for all involved. After all, if momma ain’t happy… We all know how that ends!

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17 thoughts on “Holiday Travel Tips and a Winter Travel Outfit

  1. Definitely some great tips Jo-Lynne!
    I know my mom & Nancy usually get travel insurance especially in case something happens to their health, but I never thought about it for them cancelling a flight!
    I try to wear my heaviest items on the plane too!
    The great thing about travelling during the holidays—people watching!!

  2. These are great tips! One other travel tip I learned from an earlier post of yours is, when planning outfits for travel, start with shoes- that really works for me! I look forward to coffee and your blog each morning!

  3. Thanks for the tips – I’m traveling next week and needed a little boost to get my act together. Also watched a Hallmark Christmas movie last night and you are a dead ringer for the lead actress….movie was Christmas Incorporated and the actress was Shenae Grimes-Beech!

  4. We are leaving for Italy in 3 short weeks they have had 2 earthquakes and a tordnado
    in the last 2 weeks. We are regretting not getting the travel insurance. We are going on a wing and a prayer right now #lessonlearned P.S. Love all the packing tips I will be the trourist in black gray and camel!

  5. Love your ideas for traveling. Coordinating clothing is the key. I need to remember that when I make purchases. You asked us we had any questions that you could answer on your blog. You have made me try ideas that I wouldn’t even have thought of before like pattern mixing Could you give us some of your suggestions for using brown boots instead of black with a blackish outfit? This is out of my comfort zone but looks really good when you do it! You might have covered it before but I’ve forgotten. By the way, I love the sweater you’re wearing in this post!

  6. Hi Jo Lynne! Are you liking your Bernardo jacket? Does it fit true to size! Also, what size are you wearing? Thanks so much! Freezing in MN!

    1. Hey Jeanie, I loved it, but it was a medium and a little snug when zipped, so I actually returned it. When I look at these pictures, I always wish I’d kept it or tried the large. It has such a nice shape to it.

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