Where to Go for Holiday Cheer

Traveling during the holidays is tradition for a lot of people. We tend to stay close to home during November and December, but we are lucky to have our family in town. People often plan to travel for the holidays all year long, for different reasons and occasions. Looking for holiday cheer? Here are the states with the most and least. 

infographic credit

Last year, New Hampshire ranked #1 for the second year in a row as most spirited, and Wisconsin moved from #16 to #2. For some reason, Oregon ranked 49th, only beating out Alabama and DC. Oddly, we have so many holiday markets and events, so I have no idea why we rank so low, but I guess what matters is how you feel on your own. Maybe we don't Google enough holiday stuff or stream enough Christmas music or tweet about the season. 

Whatever the case, I'm glad that more people have been influenced to spend more time with family because of the pandemic. Family can be important, if you enjoy them, and can do wonders for your mental health and happiness. If yours don't, I hope you have a friend group that is family for you and have celebrations surrounded by the ones you love.

Or maybe you just want to travel to a state that's more Christmassy. In that case, here are 20 cities for you to check out. And here are 30 more for taking a spirited winter getaway. 

Do you agree with your state's ranking? Where will you be spending your holiday season?

6 Packing Light Tips for Winter Trips

Packing even for a beach trip in just a carry-on can be a little tricky if you aren’t used to packing light. Carry-on travel has become more and more popular as baggage fees have become the norm among most airlines. 

Not only does packing light save money, but it also saves time, because travelers don’t have to stand around the baggage carousel waiting for their luggage to (hopefully) make it off the plane. Having minimal baggage can save your back, too. Not sure where to start when planning your winter travel bag? Here are some tips to keep your carry-on light, but still have a large wardrobe.

Mix and Match

When you carry fewer items, you need all your clothing to work together. Throw out the idea of packing a whole outfit for each day and instead look to mix and match everything you bring. Pick a color palette and stick with it, or make sure either all your tops or all your bottoms are a neutral color. If all your tops go with all your bottoms, you’ll find your choices are more than expected.

Scale Down

The only one who will know that you’ve worn the same clothing separates more than once on vacation is you (and your travel companions). It’s unlikely you will see the same people more than once on a trip, and if you do, they probably won’t notice that your outfit is similar to what they saw you in before. The magic numbers for what to bring: Five tops and three bottoms. These, coupled with the outfit you’ve traveled in, net you over three weeks of unique outfit combinations.

Layer, Layer, Layer

Just because it’s cold today, doesn’t mean it will be tomorrow. Plan for days that can vary in temperature by packing layers. You might have an unseasonably warm day in the middle of winter or an unexpected cold snap in fall. Be prepared. Pack a few sweaters, a scarf and a mix of tanks and tees. When it’s warmer out, you can opt for a t-shirt. When it’s really cold, you can add two or more layers together to keep chill out. If you’ve brought a dress, toss a pair of tights into your bag to protect your legs. Don’t forget your favorite jacket, which you should leave out of your carry-on to save space for other necessities. It can double as a pillow on the plane or can be stashed under the seat in front of you.

Choose Two

Shoes are the biggest challenge of everyone’s travel bag, it seems. A pair of flip flops is a staple to any carry-on, as they take up little room and are perfect for quick jaunts to the lobby or to the hotel pool. Other than those, two pair of shoes is all you need. When your destination is projected to be cool, a pair of comfortable boots and another pair of walking shoes are going to be your best bet. Don’t bring anything you haven’t worn before or that you can’t walk in for long periods of time comfortably.

Wear your walking shoes on the plane and leave your dress up shoes at home. You’re not going to want to wear high heels after a day of sightseeing. If you really want to wear a pair of nice shoes out, look for a fun pair of ballet flats or wedge booties that will go with other outfits as well.

Accessorize

If you feel that what you’ve brought is kind of drab and not really exciting for a night out, then accessories will elevate those plain Jane items. A scarf, a belt and some statement jewelry can pack small and make a big impact. Jazz up your little black dress or a simple tank with a funky necklace. Even if you’re specifically planning to go to an upscale restaurant or clubbing, you probably won’t feel like leaving your fancier clothes at home was a bad idea. If you aren’t going to wear something two or more times, it is just taking up valuable real estate in your carry-on.

Do Laundry

There’s no way around it. If you pack light and you’re gone for more than a week, you’re going to have to do laundry. Schedule some downtime (which you should do anyway) to clean your clothes. It doesn’t sound fun, but you can take the time to hit the pool, watch a show or catch a nap. Just need to freshen up a piece? Spray some vodka on it. It deodorizes, and since it doesn’t have its own smell, you won’t reek of booze.

Carry-on packing can be difficult at first, but with some practice you can become a pro and save baggage fees. With fewer bags to deal with, you’ll feel freer as you waltz off the plane and get right onto your vacation while everyone else is still waiting for their suitcases. 

Necessary Holiday Travel Tips

The holidays are coming and that means braving the crowds and being ready for all the extra headaches that come along with it, including delayed and even cancelled flights. Soon you'll join the millions of people traveling to visit friends and family or, if you're lucky, going on a winter getaway. I definitely approve of those, because the holidays can be stressful and getting away from everything is always nice and relaxing.

The airport during the holidays is a madhouse and security lines can be longer than usual, so let's talk about how to get through them with as little annoyance as possible (at least when it comes to yourself). This year will see a lot more delayed and cancelled flights due to pilot and crew shortages. 

Sign up for TSA PreCheck

You probably have time to apply for PreCheck and get approved before the holidays, since the government has restarted processing applications. For $85, you get 5 years of bypassing the main security lines and going through a much shorter line with less strict rules. You can keep your jacket, hat, belt and shoes on and your laptop and toiletries can stay in your bag. When we were up for renewal, we decided to upgrade to Global Entry, which works internationally and also includes domestic PreCheck for just $100. We used it on our trip back from France and we were able to use the Global Entry monitors and skipped the long customs line and ended up going straight to an agent while everyone else was waiting. Both of these require you to go through a Federal background check for approval.

Get There Early

Longer lines mean longer wait times and the holidays means more traffic. Don't cut it too close to get to the airport. Give yourself at least two to three hours before your flight if it's domestic and three to three and a half if it's international at the airport. Accidents happen, extra long lines happen, computer glitches happen. Just be prepared. Bring a book or magazine to keep you occupied if you end up having a long wait at the gate...or go check out your airport's art or do some gift shopping. 

Fly With Just a Carry-On

I've been flying with just a carry-on for a decade now. I've gotten my packing down to almost just the bare essentials, since I now know what will get worn and what won't. The trick to packing small in the winter is layering and not caring if all your pictures are you wearing the same coat and scarf (maybe two). Here's a post I did on packing light in the winter.

Don't Wrap Any Gifts

If you are visiting friends and family and haven't shipped your presents ahead (which I highly recommend), don't wrap them and stash them in your carry-on. TSA may very well want to inspect them and will not be sorry for you if they have to unwrap them. So, I suggest packing small gifts and saving the wrapping for when you arrive. This takes up much less room too. If you need travel gift ideas, check out this post.

Go Left

Most people get to the security lines and head right to go through the x-ray machines. This makes these lines longer. Instead, go left if given a choice. These lines are shorter, making them a bit faster. Try skipping any lines with small kids, because they usually take longer.

Keep a Zip-Top Bag On Hand

Always have a bunch of things in your pockets? If you don't have an empty accessible pocket on your bag, have a plastic bag with you and then empty your pockets into it, so it doesn't get lost in the bottom of your bag or you don't have to stand at the end of the conveyor picking everything out of one of those little round bins to load your pockets back up.

Have Your Liquids Bag and Laptop Easily Accessible 

This is super annoying. All your liquids need to fit in a one quart see through bag in 3.4oz or less containers. Have this out and ready to toss in the security bin along with your shoes and laptop. When you're holding of the line rummaging for things that you knew you needed to have out, everyone gets that much more irritated and grumpy. You saw the signs. Don't pretend you didn't.

Wear Slip-On Shoes

Having to tie and untie your shoes to get through security is just another hassle you don't need. Pack those in your bag and wear some easy on easy off shoes. You will thank me. Anything that's hassle-free is nice, and can get you on your trip faster.

Don't Wear Any Accessories 

If you can get away with it, skip the jewelry and watch and belt. Those are just more things you'll need to take off to put through the scanners and nobody wants to wait behind you while you're spending an extra five minutes de- and re-accessorizing.

Download Your Airline's App

Carry one less thing. You're already walking around with your phone, so download your airline's app so you can easily check in, get updates and have your boarding pass on hand instead of stuffing it into your pocket or a book and then having a small panic attack when you can't find it. You can have everyone's boarding pass in your party on your app. Another brilliant tip: screenshot your boarding passes in case your app logs you out or the airport has shoddy WiFi right before you need to show it to someone. This has totally happened to me more than once. Never again!

Your Chill

Don't be that person who gets all irritated when things don't go your way. Everyone's trying their best, the airline employees are already dealing with dozens of jerky people everyday. Don't make their life harder. Just close your eyes and breathe before you start yelling. Find your chill. Ask if it's really that important. Everyone's having a hard time, but they're dealing with it. Lots of things can't be helped, so you being grouchy and mean isn't going to change anything.

The holidays are supposed to be a happy time. Smile, even when you don't want to, think of the awesome trip you're about to go one, play games with your travel buddies and think of this as just another part of your adventure.

Don't Forget:

With Covid still hanging around, make sure you're staying safe, because having to quarantine from everyone in the middle of a trip due to sickness isn't going to be fun at all. We still wear our masks on planes, in the airport, and crowded indoor spaces (ex.: we wear them in grocery stores, sporting events, concerts, and while waiting in inside lines at amusement parks.) 

Aside from voluntary (but I think still necessary) masks, make sure to bring hand sanitizer, anti-bacterial wipes, and a few Covid self-tests for each person in your party. If you're trying to make your flight more comfortable, a short list of must-haves is:

• compression socks
• eye mask
• noise-cancelling headphones
• a reusable water bottle
• snacks from home (or purchased before you get on the plane, because chances are they will still be cheaper than once you're airborne).

With a little pre-planning, you can make holiday travel as comfortable and stress-free as possible. Stats say that, despite the cost of travel and the inconvenience, over 70% of people surveyed plan on traveling for at least some of the holiday season, with half of them saying they're traveling more than last year. Most are looking at spending less on holiday gifts, but also many prioritize experiences over physical gifts. This has been my and Eric's approach for years and we take a trip at the beginning of the year instead of exchanging gifts with each other.

Where will you be going for the holidays?

Disclaimer: This post includes affiliate links and I may be financially compensated if you make a purchase through one of the links. This allows me to keep this blog running, so thank you in advance.