When to Start Planning a Big Trip (and Why Waiting Costs You More Than You Think)
At a Glance
Planning a big trip takes more time than most people expect — especially for Europe, safaris, and family travel during peak seasons. In this post, I break down when you should actually start planning, why waiting often limits your options, and how starting early leads to a smoother, more thoughtful travel experience.
January does this funny thing.
Suddenly, everyone’s back at work, back in routines, and back to thinking a little bigger. You start saying things like, “This is the year we finally do that trip.” Europe. Safari. A big family trip. A milestone celebration.
And then… life kicks back in. The calendar fills. The planning feels overwhelming. And that trip quietly slides to the bottom of the list again.
Here’s the thing most people don’t realize: when it comes to big trips, waiting almost always makes them harder, more limited, and more expensive. Not because travel advisors are trying to rush you — but because the best experiences simply take time to design.
Let’s talk about what “starting early” actually means, and why it matters more than you think.
Big trips don’t come together the way weekend getaways do
If you’re booking a quick long weekend or a familiar destination, you can usually make it work on shorter notice. Big trips are different.
When you’re planning something meaningful — a multi-city Europe itinerary, a safari, or a once-in-a-decade family trip — there are a lot of moving pieces behind the scenes:
The right hotels (not just what’s left)
Guides who actually elevate the experience
Logical routing so you’re not wasting days in transit
Availability that aligns with school schedules, seasons, and events
Time to adjust the itinerary so it feels right for you
None of that happens well in a rush.
How far in advance you really need to plan
People often ask, “Is it too early?” Honestly, it’s usually the opposite.
Here’s a realistic look at timing for some of the trips we plan most often:
Europe (especially spring, summer, or fall)
Ideally: 9–12 months out
This gives us access to:
Better hotel options in prime locations
Guides and experiences that sell out far in advance
Smarter pacing instead of hopping cities because that’s all that’s available
Safaris
Ideally: 12+ months out
Safari planning is very availability-driven. The best lodges only have a handful of rooms, and peak wildlife seasons fill quickly. Waiting doesn’t usually save money — it just limits choices.
Family trips tied to school schedules
Ideally: 8–10 months out
When everyone travels during the same windows, the best-fit resorts, rooms, and flight options go first. Planning early makes family travel smoother, not more complicated.
What actually gets harder when you wait
Waiting doesn’t just affect availability. It changes the quality of the trip.
When planning starts late:
You’re choosing from what’s left, not what’s best
Prices are higher, especially for flights and top hotels
The itinerary feels more forced than thoughtful
There’s less room to customize or slow things down
And perhaps most importantly — it adds stress to something that’s supposed to feel exciting.
Starting early doesn’t mean locking everything in
This part surprises people.
Starting the planning conversation early doesn’t mean you need every detail finalized right away. It means we have space to:
Talk through what kind of trip you actually want
Explore a couple of routes or destinations
Adjust based on budget, timing, or priorities
Build the trip intentionally instead of reactively
The best itineraries almost always evolve over time. That evolution is where the magic happens.
Who benefits most from starting early
If any of these sound like you, earlier is better:
You’re planning a milestone trip and want it to feel special
You’re traveling during peak seasons or school breaks
You care about where you stay and how the trip flows
You don’t want planning to feel like a second job
In other words — if you value ease, thoughtfulness, and getting it right.
A gentle nudge if 2026 is on your radar
If you’re even thinking about a big trip next year, now is the right time to start the conversation. Not because anything needs to be booked tomorrow, but because good travel is designed — not rushed.
And when it’s done well, it feels effortless.
If that’s the kind of trip you’re dreaming about, I’d love to help you plan it. Let's. start the conversation today with our Trip Design Form.
FAQ: Planning a Big Trip
How far in advance should I start planning a big trip?
For most big trips, starting 9–12 months in advance is ideal. This is especially true for Europe travel, safaris, and family trips tied to school schedules. Planning early gives you access to better hotels, guides, and flight options — and allows time to shape the trip around what actually matters to you.
Is it ever too early to plan a trip?
Rarely. Starting early doesn’t mean booking everything right away. It means beginning the conversation, exploring options, and building the trip intentionally instead of rushing decisions later.
Does planning early really save money?
Planning early doesn’t always mean a lower total cost, but it often means better value. You’re more likely to secure preferred hotels, better flight routing, and experiences that sell out early — instead of paying more for what’s left.
What trips need the most advance planning?
Safaris, multi-country Europe itineraries, and peak-season family travel benefit most from early planning. These trips are availability-driven and involve multiple moving parts that take time to coordinate well.
When should I start planning a 2026 trip?
If 2026 travel is on your radar, now is the right time to start the conversation. Early planning allows for flexibility, better options, and a more seamless experience overall.
Do I need to have all my details decided before reaching out?
Not at all. Many clients start with a general idea and refine details through the planning process. That’s part of what we do — helping turn a loose vision into a well-designed trip.
You might also find these helpful as you start thinking through what kind of trip you want to plan:
From City to Safari: My South Africa Escape That Had It All
Milk + Honey Traveler Spotlight: A Transformative Family Journey to Ghana