Why Some Trips Need to Be Planned a Year Out (And How to Know If Yours Is One of Them) There’s a question I get asked more than almost any other: how far in advance should we start planning? And the honest answer is – it depends on what you’re trying to do! Some trips […]
Should I Start Planning Now?
Why Some Trips Need to Be Planned a Year Out
(And How to Know If Yours Is One of Them)
There’s a question I get asked more than almost any other: how far in advance should we start planning?
And the honest answer is – it depends on what you’re trying to do!
Some trips are totally fine to pull together six weeks out. Spontaneous beach week? A long weekend in a city you’ve been to before? Those come together quickly.
But there’s another category of trip entirely. The ones where your family has been saying “someday” for a few years. The multi-generational trip where you’re trying to get both sets of grandparents, your kids, and everyone’s work calendars to align. The bucket list experience that only happens during a specific window each year. The destination with one villa that’s exactly right and only has twelve beds.
THOSE trips are different. And they reward being thought about way earlier than most families realize.
The Trips That Actually Benefit From More Runway
Not every trip needs eighteen months of planning. But certain types consistently get better – not harder – when you start early.
Multi-generational trips with a lot of moving parts. When you’re coordinating travel for multiple generations, you’re not just planning a trip. You’re managing different pacing needs, different mobility considerations, different sleep schedules, and often different travel styles all at once. The families who end up with the smoothest multi-gen trips are the ones who had time to think through the flow – not just the itinerary. Where does grandma need a quiet morning? Where does the twelve-year-old need something that actually excites him? None of that gets figured out in six weeks.
Seasonal experiences where timing is everything. Cherry blossoms in Japan. Christmas markets in Europe. The Amalfi Coast in summer when the light is what you came for. Tulip fields in the Netherlands in April. These aren’t just destinations – they’re experiences that exist for a short window each year. Miss the window by two weeks and you’ve missed it. Getting the timing right takes either a lot of research or someone who already knows. And either way, it takes time to book around.
Accommodations that actually matter. There’s a real difference between a hotel room and the right hotel for your family. I’ve had families tell me they don’t care much about where they stay – until they’re in a property that doesn’t work and there’s no fixing it. The accommodations that change a trip – the ones with the courtyard that your kids will remember, or the terrace where everyone had that spontaneous dinner at ten o’clock at night – those book early. They go fast. They’re not sitting there waiting when you decide to plan in February for June.
Bucket list trips that have a real logistics layer. Antarctica expeditions. Safari itineraries timed to the Great Migration. River cruises through Europe during peak fall foliage. These aren’t just complex – they’re limited. The best cabins, the best departure dates, the best guides – none of that is available to the people who start asking about it in April.
What “Planning Early” Actually Means (It’s Not a Down Payment)
Here’s what I want families to understand: starting early doesn’t mean you need to hand over a credit card today.
What it means is: you have time to figure out what you actually want before you start booking it.
The first conversation I have with a family isn’t “what hotels do you want?” It’s closer to: what’s motivating you to do this trip right now? What does the best version of this look like – not just the itinerary, but the feeling you want everyone to walk away with?
Those conversations take time to have well. And when families skip them because they’re in a rush, the trips end up over-scheduled, under-considered, and missing the one thing that would have made it theirs.
Starting a year out means you get to think. You get to sleep on it. You get to say “actually, I think we want Florence more than Rome” – and there’s still time to rebuild around that.
The Destinations Worth Putting On Your 2027 Radar Right Now
If any of these have been creeping into your daydreams, that’s useful information:
- Italy – and specifically Florence as a home base. Day trips to Siena, Assisi, Cinque Terre. Three nights in Rome to hit the big things, then move on. Italy is for families who love great food AND care about history – the art history alone is worth the trip. If that’s your family, 2027 is a good time to start talking about it.
- Paris – works in every season, for every combination of ages. Paris at Christmas is its own thing entirely. I’ve built itineraries around it and I’m still not over how magical it is!
- Europe’s Christmas markets – late November through December, and they fill up earlier than families expect. River cruise or independent itinerary, this is a seasonal experience that books fast.
- Amalfi Coast – summer to early fall is when it’s at its most iconic. It’s genuinely on my personal travel list, and it’s also a consistent answer when families tell me they want Italy to feel a little more glamorous.
- Japan in cherry blossom season – March to April, fleeting, and one of those things people spend years saying “someday” about. The logistics require real lead time to do right.
How to Know If Your Trip Is in This Category
If any of these are true, you’re probably in “start earlier than you think” territory:
- You’re trying to coordinate multiple generations with different needs.
- The experience you want only happens during a specific season.
- You’ve been calling it “someday” for more than two years.
- There are more than eight people involved.
- You’re thinking about a destination that genuinely requires expertise to navigate well.
If two or three of those are true at once – the runway matters even more.
You don’t have to know exactly what you want yet. That’s actually what the first conversation is for.
But if 2027 has started to feel less like a dream and more like a plan, this is a good time to let me know.
I’d love to talk about what that trip could actually look like.
