When’s the Best Time to Book a Trip? CIRE’s Month-by-Month Guide to Travel Planning

By Jamie Edwards

Every year, like clockwork, mid-September rolls around, and I find myself wide awake at 3 a.m., gripped by a familiar panic. The holidays are coming, and I haven’t planned a thing. Where are we going for Christmas? Why haven’t I booked our flights? Are all the best hotels already taken? How is it that a holiday that happens at the same time every year always seems to sneak up on me?

There are all types of travel planners in the world. And despite my line of work, I often forget to plan travel. Advanced planning has inherent benefits, but there’s no need to beat yourself up if you can’t (or don’t want to) book travel a year out. Fabulous experiences await regardless of how or when you determine your next adventure as long as you keep an open mind.

The travel advisors at CIRE are ready and waiting to help every type of planner curate trips throughout the year. Every year. So, what type of travel planner are you? Let’s find out.

The Early Bird

Early Bird travel planners are the ones we love to hate. They snag the most coveted restaurants at prime dining hours, having researched the reservation rules far in advance. They get the hotels they want, and the rooms they want, at the destinations they want. They take advantage of lower airfares. These uber-planners take travel planning to stratospheric levels. The benefits of early planning are evident. But, perhaps the biggest perk of being an Early Bird planner is lower stress levels. Yet another reason to hate them.

Travel advisors love Early Birds because they can spend time creating extraordinary experiences with every detail fine-tuned. Advisors uncover exclusive deals, suggest more convenient flight routes, and even have the luxury of scouting for hidden gems. If you’re not an Early Bird, don’t worry—your travel advisor will still work wonders for you, even under pressure.

The Outsourcer

The Outsourcer is strapped for time. They are busy professionals or parents juggling a packed schedule. They have the big picture in mind—where they want to go, when, and maybe even the type of trip they want. But when it comes to details and execution, they call in the experts.

For Outsourcers, CIRE Travel is a lifeline. They handle the nitty-gritty so you can focus on enjoying the trip. Over time, your advisor learns your travel preferences—like aisle seats for shorter flights and window seats for long hauls. They know you prefer quiet, luxury boutique hotels rather than over-the-top glam. Every trip they plan makes the next one even more seamless.

The Procrastinator

We’ve all been there, booking a last-minute trip and crossing our fingers everything goes as planned. There’s a certain kind of thrill to spontaneous travel—some of my favorite trips were made on a whim. The key? Staying flexible and open-minded.

While the Procrastinator might not always get their first choices, they may stumble upon something even better, more exciting, and unexpected. Travel advisors specialize in turning last-minute bookings into unforgettable adventures, often discovering unique places before everyone else.

Other benefits of last-minute planning could be lower airfares (especially when dates are flexible) and the inherent thrill of spontaneity. Be kind to your travel advisors, dear procrastinators, as they will be under a tighter deadline than usual. But rest assured, they’ll find you a vacation to suit your travel needs and style.

10 Trips to Plan (At Least) One Year in Advance

Some adventures demand early planning due to limited availability or the popularity of the destination. In others, it’s due to logistics, for instance, when visas or special permits are required. These trips might even encourage Procrastinators and Outsourcers to start planning like Early Birds. Here are ten bucket-list adventures to book at least one year in advance:

  1. Cherry Blossom Viewing in Japan
  2. The Wildebeest Migration in Kenya
  3. A Nile Cruise in Egypt
  4. Carnaval in Rio de Janeiro
  5. Trekking Machu Picchu in Peru
  6. Tracking Silverback Gorillas in Uganda
  7. An Expedition in Antarctica
  8. Climbing Mount Kilimanjaro in Tanzania
  9. Hiking The Tiger’s Nest in Bhutan
  10. Running with the Bulls in Pamplona, Spain

The CIRE Travel Planning Calendar

Whether you’re an Early Bird, Outsourcer, or Procrastinator, consider adhering to a planning calendar to stay on top of travel. CIRE’s month-by-month guide follows. It can help you plan your dream vacations in a stress-free manner. Extra credit to those who set reminders for key dates to get the travel ball rolling.

September-October: It’s that time of year. The kids are back in school, carpools are organized, and some semblance of normality is resuming. Pat yourself on the back. You’ve made it through another crazy summer. But don’t let that freshly mown grass grow under your feet. Getting next summer’s vacation in the works now will prevent it from sneaking up on you later.

November-December: As the days get shorter, consider your long-term travel goals. Write a wish list that spans the next few years. Don’t hold back. Then, share it with your travel advisor, who can help organize, prioritize, and plan it within your budget.

January: The beginning of the year can be cold and bleak. But this is the ideal time to think about Fall. Yes, Fall! If you wait until late August to organize a colorful, leafy weekend in Stowe, you’ll discover that every inn and lodge has been booked since early spring. Consider maximizing long weekends. Adding a day on one or both ends can ease the hassle of traveling at peak times, especially when flights are involved.

February-March: Though the festive season feels far away, planning for Thanksgiving, Christmas, and Hanukkah in advance is a gift. Not only will you be able to get those coveted early morning flights (the ones that, on average, have the fewest delays), but you’ll also have one less item on your holiday to-do list to stress about.

June-August: School’s out! While the kids enjoy their summer break, start organizing spring break. Grab those coveted beachy, family-friendly hotels before they disappear. If you typically take this vacation with another family or two, get them on board now.

Travel Planning Tips and Tricks

Every kind of planner can benefit from expert guidance. Here are a few tips and tricks to help make your hard-earned holidays run smoothly.

  1. When looking at the calendar, consider school breaks. Most schools have a ‘Year-at-a-Glance’ page so parents can plan accordingly. Conversely, for those who’d prefer not to spend their vacation with hordes of teenagers and toddlers, avoid those dates like the plague.
  2. Think about traveling on the shoulder season or even off-season for lower rates and fewer crowds.
  3. Plan around world events, like Wimbledon, Oktoberfest, or Mardi Gras, in advance. Or plan to avoid them. Unless you’d rather experience The Big Easy with thousands of tipsy tourists.
  4. Always check passports are up to date and research visas and immunizations that may be required.
  5. If you have time and flexibility, fly by the seat of your pants. The surprises accompanying this kind of travel will be fodder for the vacation tales you tell time and time again.

Just Plan It

Having trips to look forward to throughout the year makes the routine of daily life more tolerable. Don’t underestimate the calm you’ll feel knowing your vacations are in the books. But, remember—if you don’t plan it, it won’t happen. Get those trips in the works. Then try not to be smug when friends scramble for hotels and reasonable airfares.

Whether you’re an Early Bird, an Outsourcer, or a Procrastinator, CIRE is there to help. My relationship with CIRE means no more 3 a.m. panicked wake-ups about travel. This leaves me free to panic about more pressing things, like what I’m making for dinner tonight.

I think I’ll just make a reservation.

Jamie Edwards 2023

Jamie Edwards is an avid traveler, travel writer, and photographer. After 25 years of living and traveling around the globe, she launched I am Lost and Found, her adventure/luxury travel website. Jamie’s goal is simple: to inspire travel.

CIRE Travel is a full-service travel agency headquartered in New York, NY.  Our expert corporate travel planners, honeymoon travel agents, and luxury travel planners support clients across the country and around the world.


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