How I Pack for Holiday Travel
- Sam Wheeler

- Nov 13, 2021
- 6 min read
Updated: Nov 19, 2021
Traveling from warm weather to cold weather and vice versa.

We are officially in the holiday travel season!! Woot woot! For many, this may have always included long hours and/or days of travel to get to their destination. I have had the luxury of only having a scenic New England-esc 4 hour drive from Milford, ME to Derry, NH for the past 6 years. Not only has that changed (still short travel time but will be earning my wings from now on) but what and how I pack is significantly going to change. When I would drive down to NH, I had my whole car to put items in, I could have a suitcase and whatever other bags I needed and room to put things I buy from Black Friday shopping/Christmas shopping. That clearly cannot happen now, so I have to be very strategic and aware of what I pack and how much I pack. Therefore, I decided to dedicate a post, that nobody asked for, about how the heck I am going to go about doing this.
So let's jump right on into this!
Tip #1 - Avoid Checking a Bag
Traveling by plane versus car is definitely more expensive. Thank goodness for Allegiant because flights are much cheaper than higher-profile airlines and leaving your car in long-term parking also isn't horrible. But listen, your girl is always looking for more ways to save money cause we living that paycheck to paycheck life on steroids, so anyway I can save move, Imma do it. Not checking a bag is practically a no-brainer. However, that means I have less space to pack things, which stinks because I tend to like to pack extra as in case of emergencies (emergencies being that I spill food on myself or I get indecisive the day of me putting on an outfit that I picked out a week earlier). It's fine though, everything's fine and it is totally worth it to save some money. Other than the fact that you save money not having a checked bag, you are completely avoiding the possibility of losing your bag at bag pick-up. Granted, sometimes I will volunteer my bag if there is a full flight and they need space, but you are way less likely to lose it then. Or at least that is what I tell myself so don't tell me I'm wrong.
Tip #2 - Utilize My Personal Item
I love my personal item. This is basically my lifeline when traveling and use a big 'ole backpack as my personal item.
Side note: does anyone else sing this from Dora the Explorer in their head when they say the word backpack:
Backpack, backpack, backpack, backpack, I'm the backpack loaded up with things and knickknacks too, anything that you might need I got inside for you.
Yes? No? Just me? Okay, sweet. But I will say that if you haven't you certainly will now. You're welcome.
My favorite backpack right now is the one I got from IKEA (Kevin actually got it for me when we first came down here and we're exploring Florida before he had to fly back to Maine). Also, side tangent because I have not done this yet in the post, IKEA is fantastic and there is one in Orlando and I had not been in one for a very long time. And no, we did not get the Swedish meatballs (one, because I cannot eat them cause of that gluten and meatballs from a store like IKEA, freaks Kevin out, I mean I get it). Why I love this bag is because it is large but not clunky, has a zipper pocket on the back so you can access items in your bag without having to open the whole dang thing, has a front zipper pocket with convenient slots, and two, yep TWO pockets for drinks. I use this as my work bag in addition to my personal item. Highly recommend.
What actually goes into my backpack depends on where I am going, how long my flight is, how early I get to the airport, what mood I'm in, if its' a full moon, etc., etc., etc.
Here are the basics:

Empty water bottle. Hydration nation.
Gum. Since my ears hate the change in altitude and it helps alleviate any nausea I have from the stress of flying. P.S. I have a total love-hate relationship with flying. I love everything about going to the airport but actually getting on the plane and going a bazillion miles high in the air, no thank you
Phone, charger, headphones, and power bank. In case I cannot find a spot next to an outlet, which we all know can be impossible at the airport)
Downloaded books and podcasts on Audible. I just recently had a free audible download with a free trial of the premium of Audible but this broke girl straight up signed up for the premium, downloaded my free book, and then canceled the subscription BOOM. What I have for this trip home is the new Stanley Tucci book, Taste (very excited about this one, I freaking love Stanely Tucci), and Morbid: A True Crime Podcast (I am obsessed with this podcast, y'all need to check it out if you like podcasts and true crime).
Snacks. Cause this girl loves to eat and airport food is waaaaaaaay too expensive for this frugal female.
Cardigan. It can get super cold at the airport and on the plane so if I don't have one wrapped around my waist like a cool person, it is most likely in my backpack.
A laptop or iPad. Usually, it is my iPad I bring with me to have as another means of listening to music, podcasts, or movies on the flight and if I have to do any work when I am away. This time around, I will be bringing my laptop (just recently got an Acer Chromebook to have at home for late nights and to work on this blog since I am apparently a blogger now thanks to you guys :)
Tip #3 - Choose & Pack Organized Outfits
This is the part I always struggle with and this trip is going to be so much worse. I stink at packing lightly. I mean STINK AT IT. I always have good intentions going in but I always need to have backups to my backups. Can't really do that this time since I want to leave some space for items that I realize I forgot to bring with me from Maine when I go to visit or if (I mean when) I go Black Friday shopping with Momma Wheels. One nice thing about moving to Florida, I did not bring that much cold-weather attire cause Florida, which narrows down what I will be able to bring to New England anyways. And guys!!! I AM SO EXCITED TO WEAR COLD-WEATHER ATTIRE! I honestly miss being able to wear sweaters, vests, boots, etc. without the possibility of sweating my butt off. It is still weird to me that I am not doing that right now. I am literally writing this post in shorts and a t-shirt with the windows and my patio door wide open in mid-November. My goal is to pick 7 outfits for my trip but bring pieces that I can re-wear in different outfits. I usually only bring two pairs of jeans, a few tops, a cardigan, and two pairs of shoes (including what I will be wearing to the airport). I have everything picked out but let's see how it will fit.
Tip #4 - Trial and Error to the Perfect Pack
If anyone had ever traveled with me recently, so basically by BFF Brynne and Kevin haha, you know that I tend to re-pack my bags multiple times throughout the trip. It is either due to purchasing souvenirs and needing to make things fit, or it just turns into a cluster and it just needs to be re-organized, or I am bored/stressed and it is something to do. I know myself enough that no matter how well I pack initially, this is going to happen at least once during my trip. Even still, I find that the better organized I have my carry-on in the beginning and the more efficient I am in packing (basically the amount that I pack) the better things are for everyone. What I have found to help me is getting packing cubes from Amazon. These things are a total game-changer and make it so much easier to get things to fit and stay organized. Another item I highly recommend.
*This straight up, 100%, full disclosure took me an hour+ to get to this stage.*
To say that I am excited to be traveling home for the Thanksgiving holiday is a complete and total understatement. I get to spend a few days in Maine (all my Maine peeps, where you at!? I want to see your beautiful faces) and then the rest in New Hampshire, and it will be the best reset I need. I know it is going to make me even more homesick but that just means I will need to make more trips up North throughout the year. Good thing I somewhat know what I am doing when it comes to packing haha.
What tips and tricks do you have up your sleeve when it comes to traveling for the holidays? Leave a comment for me and fellow readers!

Be sure to check back here/follow along to hear about my excursions in New England and if I am able to get everything back to Florida!









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