When Is the Best Time to Book a Winter Vacation?

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Pam MacIntyre

Maple Grove, MN
Australia & New Zealand Specialist

New Zealand

In all my years as a Travel Professional, I’ve asked countless people, “What’s on your must-see list?” And without fail, New Zealand is always at the top! Honestly, who wouldn’t want to experience this majestic ...

Thinking About Your Winter Getaway? Here’s Why Booking Early Pays Off!


Winter might feel like a distant memory right now, but in my world, it’s always just around the corner. After all, planning the perfect escape takes time—and that’s what I’ve been helping people do for a while now.


I just wrapped up my 27th winter travel season—not sure how that happened, but here we are. Come May, I’m already starting to book trips for next winter. And around this time each year, the same question always comes up:


When’s the best time to start planning my winter vacation?”


Before COVID, the sweet spot for booking was about 4 to 6 months ahead—early birds would contact me by June, another wave came in the fall, and ideally, everything was locked in before the holidays. After the new year, prices for the best resorts tend to go up.


But today? Things have changed.


Savvy travelers are booking even earlier—sometimes as soon as flights are released! Airlines like Delta, American, and United open their schedules 331 days before your return date, while others like Sun Country and Southwest release theirs around June.


Here’s why planning early is a game changer:



  • Low Deposits, Flexible Payments: Many travel options allow you to secure your trip with a small deposit, with the balance due closer to your departure date. This flexible approach helps you manage your budget without the stress of large upfront costs.

  • Budget-Friendly, Stress-Free Payments: Spreading out your payments over time makes your trip more affordable and less stressful. With extra time to budget, you might even upgrade your experience—like moving from an oceanview room to a balcony suite or from a moderate resort to a deluxe stay. After all, once you’re there, you can’t get back that time or money, so it’s worth booking the experience you truly want!

  • More Time to Choose: Booking early gives you ample time to compare destinations, accommodations, and activities. You can make informed decisions without the pressure of last-minute choices, ask questions, and explore options to find the best fit for your preferences.

  • Best Selection & Savings: Early booking often unlocks better rates and greater availability, so you can select the options you want. Last-minute deals tend to be limited and may come with higher costs or less desirable choices.

  • Peace of Mind: Securing your plans early lets you relax and enjoy the anticipation of your trip instead of stressing over last-minute arrangements. It also gives you extra time to review and book experiences before you travel, so you can fully enjoy your destination.

  • More Time to Look Forward To: With your plans set, you can focus on the fun parts of your trip—like shopping for vacation outfits and daydreaming about your getaway.


I’ve seen it time and again—travelers who plan ahead usually pay less, get exactly what they want, and skip the stress of last-minute scrambling. As your travel advisor, my goal is to make that whole process easy and stress-free, every step of the way.


There’s real value in getting ahead of the game.


If you’d like, I can even send you a yearly reminder to keep your travel plans on track—just let me know!


Thinking about a winter getaway? I’m here to help make it happen.


 

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