There’s something about September that always feels like a reset. Summer vacations are windingdown, school is back in session, and suddenly the year ahead doesn’t feel quiteso far away.

And if a specia lvacation is part of your plans for 2027, this is also the time of year when Istart telling my clients: don't wait until 2027 to start thinking about it.

Not because everyvacation needs to be booked a year in advance. It doesn't. But some tripsbecome much easier to plan when we have time on our side.

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The trips I'd be thinking about now

If Europe ison your wish list for spring or summer 2027, now is a great time to starttalking about what you want the trip to look like. Italy? Greece? France? AMediterranean cruise? Maybe a combination? The earlier conversation isn'tnecessarily about booking every detail immediately. It's about figuring out thetrip before we're forced to make decisions based solely on what's still available.

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Then there are the big family trips. Maybe 2027 is the year everyone finally gets together. Grandparents, adult children,grandchildren, cousins. Those are some of my favorite vacations to plan, butthey're also the trips where accommodations and logistics matter most.

Finding ahotel isn't difficult.

Finding the right combination of rooms, location, activities, transportation and downtime foreight, ten or fifteen people? That's where planning ahead pays off.

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But here's what I don't want you to do

Don't start booking things simply because someone tells you that you need to “book early.”

First, figure out what you actually want from the vacation.

Do you want to explore or relax?

Do you want everyone together most of the time, or would you rather have opportunities tosplit up?

Is the hotel simply somewhere to sleep, or is it an important part of the vacation?

Would you rather spend more on accommodations, experiences, private transportation or food?

Those answers matter far more to me than simply asking, “Where do you want to go?”

Because two families can travel to exactly the same destination and need two completelydifferent vacations.

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This is where I would start

If you're considering a significant trip in 2027, you don't need to have it figured outyet.

In fact, that' sthe perfect time to talk to me.

Bring me the half-formed idea.

We want to take the kids to Europe, but we don't know where.

We'd love to take everyone somewhere for our anniversary.

We've always talked about Alaska.

We want a beach vacation, but we don't want to just sit at a resort all week.

Those are some of my favorite conversations because we can start with the people taking the tripand build from there.

You don't need an itinerary yet.

You just need an idea of how you want the vacation to feel.

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RONNA'S TAKE

The best time to begin planning isn't always determined by a booking calendar. It's when youhave enough time to make thoughtful choices instead of settling for what'sleft.‍