Though the recent warm weather here in California may have you thinking otherwise, the holidays are rapidly approaching. And if you want a smooth, drama-free escape this year, the smartest thing you can do is start planning. Like, right now. Whether you’re heading to a snowy mountain lodge or back to visit the fam, a strategic approach can transform the most chaotic travel season of the year into your most joyful one.
1. Book Smarter, Earlier
When it comes to holiday travel, airfare is what you want to lock in strategically, and while the ideal time to book is actually late summer when airlines release the widest inventory, we’re now in the shoulder window where fares can still dip briefly, especially around 30 to 60 days before you travel, which could still work for the December holidays. (Same timing goes for hotels.) According to Google Flights, there’s no magic day of the week to buy holiday flights. Booking on a Tuesday versus a Sunday only changes prices by about 1%, so travelers are better off being flexible with departure days (midweek flights are still consistently cheaper) and setting price alerts to track fare drops in real time. For next year, mark your calendar for August, when airlines historically release the most competitive holiday fares and you’ll have the best shot at locking in the good stuff before demand surges.
2. Streamline Airport Day
The holidays bring long lines and jammed terminals, so buffer more time than you think you need. Pre-order airport food via apps like AtYourGate, Grab, or your Starbucks app so you can skip lines and avoid wandering around hangry in peak chaos. It’s also super helpful to order your rideshare service ahead of time, as there will certainly be surges. And arrive early for morning flights, which are statistically far less likely to be delayed. And do not wrap gifts until you arrive. TSA will absolutely make you open them if they can’t see through the packaging.
Getty Images
3. Dial in Your Carry-On Only Game
Carrying on is the single most powerful hack of the holiday season. It eliminates checked-bag lines, lost luggage stress, and carousel crowds. To do it well, build a micro capsule wardrobe in one color palette; use compression cubes; wear your heaviest items like boots and coats; bring travel-size beauty products or order full-sized versions you may need on Amazon to arrive at your destination; plan for one laundry day; roll soft items and fold structured ones; and pack an ultralight duffel for the return trip when gifts magically appear. If you must check something on the way home, put an AirTag or Tile in your luggage so you always know where it is.
Courtesy of Amazon
4. Ship Your Your Gifts (and Maybe Your Luggage)
A rising holiday hack is shipping your bags or presents ahead of time. UPS, FedEx, and dedicated luggage-shipping services like Ship & Play can send everything directly to your destination. It’s often more reliable than checking a bag during peak weeks and frees you to move through the airport hands-free.
5. Consider Ghost Airports
Secondary airports like Burbank instead of LAX, Oakland instead of SFO, and Paine Field instead of SEA often have cheaper fares, shorter lines, and far better on-time performance during winter. Of course, it’s important to consider that the FAA cuts due to the government shutdown could impact these smaller airports heavily, so it’s worth keeping up with updates on their site.
6. Rethink Holiday Conventions
A growing trend is celebrating off the actual holiday. Families and friends are hosting gatherings before or after the big days, freeing themselves up to travel when flights are cheaper, crowds are thinner, and destinations feel calmer. It’s a reset for both your budget and your sanity.
Getty Images
7. Book the Earliest Flight Possible
It may hurt to wake up at 4 a.m., but early flights are dramatically less likely to be delayed or canceled, especially during winter weather events.
8. Add Buffer Days
If you’re traveling to or from snow-prone regions like Tahoe, Montana, Wyoming, Colorado, or Utah, expect storms to cause 24 to 48 hours of ripple-effect delays even after the weather clears. Build in buffers. Even if you don’t deal with weather delays, you’ll love having a buffer day between your arrival to going back to the grind, allowing for grocery shopping, resetting, and bingeing movies.
9. Save Everything Offline
Airport WiFi and crowded terminals are notoriously glitchy, especially when they’re overloaded with travelers. Download your boarding passes, maps, transit directions, hotel confirmations, and entertainment before you go. Offline mode means instant peace of mind, and that you won’t have to raw dog your flights.
10. Rethink Holiday Travel Altogether
One of the best-kept secrets in travel is taking PTO the first week of January. Crowds evaporate, destinations shift into slower, more reflective rhythms, and wellness travelers treat it like a personal reset—sunrise beach walks, journaling, spa time, and rest before the year kicks into high gear.
We only recommend things we love. If you buy something through our site, we might earn a commission.