When to Plan and When to Book Your Trip
One of the most common questions I’m asked is, “When should I start planning my trip?” And while I wish there were one easy answer, the timeline can vary pretty drastically depending on where you’re going and what kind of trip you’re planning.
A week in the Caribbean is very different from a multi-country European itinerary. A safari has its own set of logistics, while a trip built around specific hotels, experiences or dates may require getting started even earlier.
As a general rule, I’d rather have more time and more options than be working around what’s left. That’s especially true for trips during peak seasons, holidays and other high-demand travel periods.
When should you start planning?
For Europe, I generally recommend beginning the planning process around 10 months out. Safaris often need an even longer runway, closer to 10–14 months, while the Maldives and Indian Ocean are typically best planned 8–10 months ahead.
For Southeast Asia, 6–10 months is a good starting point, and for the Caribbean, I typically recommend 6–8 months. If we’re putting together a more complex, multi-country itinerary, starting 12+ months in advance gives us the best opportunity to build the trip the way we want it.
Of course, every trip is different. These aren't hard-and-fast deadlines, but they are good guidelines if you want the best hotel availability, room categories and itinerary options.
Let’s Chat Flights
This is the part that often gets overlooked. When you start planning your trip and when you book your flights aren't necessarily the same thing.
In many cases, I actually want the itinerary to begin taking shape before flights are locked in. That gives us the opportunity to determine the best arrival and departure cities, how the trip should flow and which flight times make the most sense for the itinerary, rather than building the entire trip around flights that have already been booked.
For Europe, I typically recommend booking flights around 4–7 months ahead. For safaris, the Maldives and Indian Ocean, and complex multi-country trips, 6–9 months is a good rule of thumb. Southeast Asia generally falls around 5–8 months, while Caribbean flights can often be booked 3–6 months out.
If you're traveling during peak summer, over the holidays, have very specific dates, or plan to fly business or first class, I recommend leaning toward the earlier end of those windows.
The takeaway
You don't necessarily need to book everything the minute you decide you want to take a trip. But you do want to start the planning process early enough that your itinerary (not limited availability) gets to drive the decisions.
And if you’re a frequent traveler or have a trip on the horizon, save the guides above for a quick reference the next time you find yourself wondering, “Is it too early to start planning?” Chances are, it probably isn’t.