How to Plan a Trip When You Don’t Have Time to Waste

There was a season of my life when planning a trip felt harder than actually going on the trip.

Between work, family, responsibilities, and the constant mental load we all carry, the idea of sitting down to research flights, hotels, activities, and itineraries felt… overwhelming. And yet, I kept feeling this pull — that life was moving fast, and I didn’t want to keep postponing the moments that matter.

Over the years, I’ve gotten much better at the planning side of things. I’ve learned which tools to use, where to look, and how to avoid decision fatigue. But the biggest shift came when I stopped trying to plan every minute — and started building in time to wander.

What I’ve learned is this:

Travel isn’t about having more time. It’s about using the time you already have — better.

Here’s the simple system I use now to plan trips without letting them become another item on my to-do list.

1. Start With the Why, Not the Where

Before you ever open Google or Pinterest, ask yourself one question:

What do I actually need from this trip?

Is it rest?

Connection?

Adventure?

Time alone?

A celebration?

When you start with the purpose, the destination often becomes obvious.

A stressed season might point you toward a quiet lakeside town or a beach resort with a spa.

A milestone birthday might whisper Mediterranean cruise or European getaway.

A busy stretch of life might mean a charming town two hours from home — the kind of weekend that lets you truly recharge.

When you know why, everything else gets easier.

2. Choose the Right Trip for This Season of Life

We change. Our lives change. Our trips should too.

Instead of asking, “Where should I go?” try asking:

• How much energy do I actually have right now?

• How many days can I truly step away?

• Do I want simple — or immersive?

  
  

Some seasons are made for long, layered journeys. Others are made for one-night getaways that reset your soul.

Both count.

3. The 3-Tool Planning Flow

This framework has saved me hours of overthinking.

Inspiration → Research → Booking

Inspiration - One or two trusted sources. That’s it. No rabbit holes.

Research - Focus only on what truly matters:

• The best area to stay

• One or two must-see experiences

• Food you’re excited about

Booking - Commit. Don’t keep circling.

4. How Far Ahead You Actually Need to Plan

You don’t need a six-month plan for every trip — but you do for some.

• Weekend getaway: 2–3 weeks out

  (unless you’re traveling for a festival or event that sells out early)

• Domestic trip: 1–3 months, depending on season and demand

• International: 3–6 months

  The six-month window is especially helpful for flights, and popular excursions often sell out early.

Give yourself permission to plan simply — not obsessively.

5. Build in White Space

Some of my favorite travel memories were never on the itinerary.

Leave room to wander. To linger. To sit with coffee and nowhere to be.

That’s where the magic lives.

What I Wish I’d Known Earlier

I used to believe that travel had to be big, sometimes even complicated, and perfectly planned to be meaningful.

Now I know this:

The best trips are the ones that feel manageable to start — and unforgettable when you return.