With a little planning — and a travel pro in your corner — you can actually enjoy the journey and the destination.
The truth? This time of year has its quirks. Flights fill fast, prices jump, and everyone’s energy is dialed up to “festive chaos.” But I’ve helped hundreds of travelers pull off smooth, even magical, holiday trips — and it always comes down to a few smart strategies (and a calm mindset).
Here are 7 tips I share with clients every year, plus a few insider twists you won’t find on just any travel blog:
#1 Book early — but don’t panic if you didn’t.
Sure, advance planning helps, but don’t assume you’ve missed your chance if you waited. Sometimes airlines quietly release last-minute inventory, or resorts run unadvertised promotions to fill the last few rooms. Flexibility can be just as valuable as timing.
👉 Pro tip: If your dates are firm, let me monitor the market for you — I often catch dips or cancellations that never hit public listings.
#2 Avoid peak dates when possible.
The difference between flying out December 21st and December 20th can be hundreds of dollars and hours of stress. Shift by even a day — or fly on the holiday itself — and you’ll find calmer airports, happier gate agents, and maybe even an extra seat to stretch out.
👉 Pro tip: Early-morning flights tend to be less delayed and less crowded, too.
#3 Pack smarter, not harder.
You don’t need to bring your entire closet to the Caribbean. Cross-pack (half your clothes in your partner’s bag, half of theirs in yours) so one lost suitcase doesn’t ruin the week. Use packing cubes to stay sane, and resist the “just in case” temptation.
👉 Pro tip: Always pack one outfit for warm weather and one for cool, even if you think you know the forecast. Planes get chilly and tropical evenings can surprise you.
#4 Know your airport game plan.
Holiday airports can be their own kind of obstacle course. Check your terminal layout in advance, use mobile boarding passes, and download the airline app for real-time updates. TSA PreCheck or Clear can feel like a holiday miracle.
👉 Pro tip: Pick flights with slightly longer layovers this time of year. It’s much better to have a relaxed airport coffee than a frantic sprint across terminals.
#5 Let someone else handle the logistics.
From airport transfers to excursions, the more you arrange before you leave, the smoother everything feels. Having a pro (hi, that’s me!) coordinate those details means fewer “Wait, who’s got the confirmation number?” moments and more actual vacation.
👉 Pro tip: Group trips? Let me collect everyone’s payments separately — no chasing down your cousin for her half.
#6 Build in buffer time.
Travel delays are more common during the holidays, so avoid scheduling anything big right after you arrive. A dinner reservation or excursion the first night sounds fun until your flight’s delayed. Give yourself a cushion — and permission to rest.
👉 Pro tip: I always suggest a “nothing day” in every itinerary. Those are often the best memories: lazy breakfasts, slow strolls, and spontaneous fun.
#7 Remember why you’re traveling.
It’s easy to let stress sneak in when the airports are packed and Aunt Linda’s texting you hourly updates. But at the end of the day, this isn’t about getting there perfectly — it’s about being there fully.
The smiles. The stories. The sunrise over somewhere new.
Because perfection isn’t the point — connection is.
If you’re traveling this season, I’m cheering you on.
And if you’d like to make it all a little easier (or start planning next year’s holiday escape before the rush hits), I’m here for that too.
Let’s make this season feel a little lighter — and a lot more joyful.