How I Plan Every Trip — Part 1 (Dates, Destination, and Getting There)

Planning a trip doesn’t have to be overwhelming — in fact, it’s one of my favorite parts of travel. I’ve broken down my go-to trip planning process into six simple steps. In Part 1, I’m sharing how I figure out when to go, where to go, and how I’ll get there.

 

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Step 1: Choose Your Dates & Length of Stay

Whether you’re working around holidays, PTO, or just want to make the most of a long weekend, this is where every trip starts.

Tips:

- Look at your calendar and holidays that give you bonus time off
- Decide how long you want to be away: 1–3 days, 4–6 (my sweet spot!), or 7–10 days

Step 2: Pick Your Destination

Got a bucket list? Great — start there. If not, ask yourself:

- Do I want to hike?

- Lay on a beach?

- Take my dog on an adventure?

Tips:

- Use Google and Instagram to research places that match your vibe

- Don’t feel tied to one city — if you’re going to Florida, explore multiple towns!

Step 3: Plan Your Transportation

Once you know where you’re going, figure out how to get there.

Tips:

- Flights: Book domestic flights 1–3 months out; international 3–6 months out

- Driving: Map your route + overnight stops if needed

- Rental cars: Book 1–2 months in advance and compare prices

Now that you’ve locked in your dates, destination, and how you’re getting there, you’re off to a strong start. In Part 2, I’ll walk through where to stay, what to eat, and how to find the best experiences — aka, the fun stuff!