Tips for Planning a Weekend Getaway Around the Holidays

joyful modest woman on square in downtown at new year night

There’s a special kind of chaos that comes with the holiday season. It’s the time of year when your calendar fills up faster than your phone storage, and you start using the word “festive” as both a compliment and a cry for help. Which is exactly why sneaking away for a weekend, just a quick breather between the gift wrapping and the endless small talk, feels so tempting.

Whether you’re escaping pre-holiday chaos, sneaking in a break between celebrations, or plotting a New Year’s reset, a short getaway can be pure magic. Think cozy lights, wintery views, and maybe a mug of something warm that doesn’t have to be shared with anyone. But to make it actually relaxing (and not just “holiday stress in a new zip code”), here are a few tried-and-true tips.

Time your escape for maximum calm

The holidays tend to shrink our free time, so if your ideal weekend is Thursday through Sunday, great. But if you can slip away Friday afternoon, or extend through Monday morning, you’ll dodge the busiest travel windows. And if you’re willing to travel on the holiday itself, you’ll breeze through airports. Less time stuck in TSA lines, more time sipping cocoa with a view.

Pick a destination with charm, not just “holiday décor overload”

When you’re choosing where to go, think “cozy twinkle” instead of “mall-Santa energy.” Look for places with real personality like local shops, festive lights that don’t require sunglasses, and cafés where you can sip something warm without being photobombed by twelve reindeer sculptures. The sweet spot is somewhere that feels spirited but not manic.

Two coffee cups placed on a surface, with a backdrop of warm, glowing lights and decorated trees, evoking a cozy holiday atmosphere.
Photo by Mâide Arslan on Pexels.com

Book lodging early, so future you can relax

Holiday weekends attract the same number of travelers as a Taylor Swift concert, so book early. The best spots, like cozy boutique hotels, charming bed-and-breakfasts, and reasonably priced downtown rooms, tend to disappear faster than you can say “sold out.” Even if you’re not sure of every detail yet, it’s worth reserving something flexible while options are still good.

Pack light, even if your holiday sweater collection says otherwise

You don’t need much for a weekend. A few layers, comfy shoes, and one outfit that looks just a little more festive. The goal is to keep your bag light enough that you don’t have to play Tetris just to close it. Remember: it’s only a few days. You’re not starring in a Hallmark movie (probably).

Exterior view of a home with a bright red door, adorned with various pumpkins and seasonal decorations on the steps, surrounded by plants and flowers.
Photo by Sasha P on Pexels.com

Choose one “wow” moment and let everything else be easy

Holiday weekends are short. Instead of trying to see every light display, parade, and artisan market, pick one highlight. Maybe it’s an incredible dinner, a snowy hike, or a stroll through a beautifully lit historic district. The rest can be flexible. You’ll enjoy your trip more if you’re not racing around. If that means you spend an afternoon reading by a window with cocoa in hand, congratulations, you’ve won the trip.

Outsmart the travel chaos

Check travel times (roads, flights) and business hours ahead of time. Holiday traffic loves to surprise you…and not in a fun way. If driving, aim to depart outside peak rush. If flying, consider less-popular airports or times. If visiting attractions, stores, or other businesses, be flexible as their hours might be different than you expected. A little cushion goes a long way.

A decorative cake with 'happy new year' written on top, surrounded by festive greenery and twinkling lights.
Photo by Iuliia Pilipeichenko on Pexels.com

Create your own traditions

You don’t have to go full turkey dinner mode to feel the holiday spirit. Maybe it’s a quiet fireside picnic instead of a crowded event or a cozy market stroll instead of a big festival. Bring a little of your own tradition along, like a playlist, a special treat, or a book you only read this time of year. The point isn’t to escape the holidays. It’s to enjoy them on your terms, ideally with less glitter involved. Seriously. Stop putting glitter everywhere, you sociopathic holiday card/gift wrap/décor companies.

Capture the moment, but actually live it too

Take photos, sure. But also set your phone down long enough to remember what the crisp air smelled like or how that random bakery made the best cinnamon rolls of your life. The best memories aren’t always the ones you post right away. And if you do post, at least include one ridiculous, honest shot, like you trying and failing to balance your cocoa and your camera in mittens in 28 degrees.

A beautifully lit street scene during the holiday season, featuring decorated trees with colorful ornaments, twinkling lights adorning the building facade, and gently falling snow creating a festive atmosphere.
Photo by Kirill Lazarev on Pexels.com

Plan your return like a pro

The only thing worse than post-holiday exhaustion is compounding it with post-getaway exhaustion. Give yourself a little breathing room on the way back. Maybe leave a bit earlier, or keep your first morning back clear of major commitments. You’ll be glad you did when you’re sipping coffee in peace instead of sprinting into reality.

Final Thoughts

Getting away during the holidays isn’t about escaping the season. It’s about rediscovering the calm hiding underneath it. A few smart choices, a sprinkle of humor, and a good travel mug can turn even a busy weekend into something you actually remember fondly.

Got a favorite place for a holiday weekend escape? Drop it in the comments. I’m always up for adding another spot to my travel list!


4 responses to “Tips for Planning a Weekend Getaway Around the Holidays”

  1. Marcy Brodsky Avatar
    Marcy Brodsky

    Love how you framed this escape plan. I actually felt a calm while reading versus a frenzy.
    Now where shall I go…..

    1. Becca Avatar

      Definitely need an update when you decide!

  2. G1 Avatar
    G1

    Hey…don’t dis the glitter🤣
    Yes, after experiencing my first FULL ON Christmas last year, your reminder of how to find some quiet is just on time!

    1. Becca Avatar

      I stand by my stance on glitter.

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