Back to school season is the most important time of the year to plan your year of trips ahead. Yes, you read that right, you should start planning for the whole year in September. Why is this time so important?
Summer has officially ended, the kids are back in school, the boys are back in town, and the ladies who lunch have resumed their seats at their favorite cafés. There’s a feeling in the air, a mixture of renewal and urgency, a perfect moment to reflect on what matters most and start planning something you can look forward to.
This isn’t just another new year marked by a change in the calendar or fireworks in the sky. It’s the first of the year that actually matters, a fresh start for your future journeys. At this moment, the Tuesday after Labor Day, the travel world stirs back to life. It’s the calm before the rush, a time when the phone starts ringing, the inbox starts filling, and everyone realizes it’s time to book their holiday trip.
For many, this is the busiest and most crucial time of the year to learn how to plan a trip or how to plan a vacation in a way that avoids the stress of last-minute decisions and skyrocketing prices. The key lies in understanding the rhythm of the industry and acting at the right moment. That’s because this is when the best accommodations including suites, private guides, and hard-to-book restaurants become available. The Tuesday after Labor Day isn’t just a day on the calendar; it’s a window of opportunity.
The advent of COVID in 2020 and the upheaval it triggered made a huge impact on how we travel today. All those canceled trips from 2020 were pushed forward into subsequent years, causing a domino effect that made desirable accommodations scarce and prices soar. It was a tough period for last-minute planners, who found their choices were either unavailable or wildly expensive. Naturally, this forced a dramatic change in habits. Today, in 2024, advanced booking isn’t a luxury, it’s a necessity.
So how to plan a trip in this climate? “Don’t be behind the curve or late to the party,” says Erica Jackowitz, co-founder of Roman & Erica and Rêve Travel Club. “Get in front of it, cancel later, and know that you can do it at little or no financial risk.”
The best travelers start thinking about their vacation plans nearly a year in advance, sometimes even longer, securing suites, guides, and dinner reservations while the rest of the world is still wondering where to go.
How to plan a vacation, then, starts with choosing your dates and your destination. But it’s more than just booking a flight; it’s designing a memory. Begin by asking yourself: How do I want to feel on this vacation? Do I want relaxation or exploration, indulgence or education?
“For many, at the top of this list, is planning out their travels with family and friends. I know this because this is our busiest week of the year,” says Jackowitz. People use this moment to reconnect and create lasting memories.
For many, this means securing a destination well in advance; a Japanese ryokan during cherry blossom season, a safari in Botswana with a private guide, or a cliffside hotel in Capri when the Amalfi is at its most magical. The best properties and guides aren’t mass-produced; there are only a handful of suites with a view, a small number of seats at a chef’s table, a limited roster of guides who specialize in a particular park. Booking early lets you choose, not settle.
When you learn how to plan a vacation this way, you’re not reacting to scarcity; you’re designing something extraordinary from the outset.
This approach applies to holiday travel, too. The last week of December, the most popular travel period of the year, doesn’t have to be hectic and rushed. If you treat it as a celebration instead of a scramble, you can create a rich, intimate holiday experience. The trick is to select a destination that feels festive and restful at once, make a few key reservations in advance, a special dinner, a spa day, a family activity, and leave space for spontaneous moments. The result is a holiday filled with indulgence, relaxation, and genuine connection.
Some of the best planners employ a simple principle: plan intentionally. They start by choosing their dates and destination. They consider their preferences and their must-dos. Then, well in advance, they book the components that matter most. That might be a suite with a view, a renowned private guide, or a dinner at a restaurant that books up a year in advance.
This kind of forward thinking transforms the vacation from a hectic, last-minute rush into a rich and restful experience, a true vacation, not just a change of scenery.
So today, raise a glass, dip into the sweetness of honey, and toast to a year filled with boundless and meaningful journeys. The future is yours to shape and it starts now. The greatest modern-day travel tip is this: The earlier you plan, the more the world opens up to you.