Your Checklist to Picking a Destination
My previous post asked “What place would make me the happiest right now to see?”
This should be your starting point, or your North Star.
Don’t get me wrong, you can absolutely get inspired by using the Explore tool on Google flights, but at the end of the day, a $100 fare to somewhere that isn’t exciting is far more expensive than a $300 flight to somewhere you have been dying to go.
Let’s get started.
Step 1: Follow Your Spark
Are you craving a big city? Maybe you desire to sit on the beach or hike in the mountains. Has there been somewhere you’ve always dreamed of going? What destination makes you feel so excited you can barely stand it?
If a place isn’t sparking this excitement or joy, don’t force it, no matter how cheap, popular or logical it seems.
Step Two: Reality Check the Logistics
OK, you’ve picked out the destination, now it is time to get practical.
This is where intention meets strategy. Here’s what I look at:
- Ease of getting there – Are flights reasonable? Are trains or other transportation reliable once I arrive?
- Where I’d stay – Are there hotels or neighborhoods that match how I want to feel on this trip?
- Transportation on the ground – Can I move around easily without stress? These days, if I don’t have to rent a car, the better (I spend too much time daily in traffic as it is. Walkable places are even more desirable.)
- Time vs. payoff – Is this a place that makes sense for the length of trip I have?
If the logistics are overly complicated for the type of experience I want, I pause and look at my plan. If my plan can’t be modified the way I am envisioning this trip, I may end up saving it for when I have additional time or energy. And, this is important, you only have so much time, and you don’t necessarily want to jam 8 days worth of stuff into 5 or spend 5 hours a day on a train.. You’re going to miss experiencing the place and end up exhausted.
Step Three: Make Sure It Works Financially without Guilt
Being intentional doesn’t mean being reckless. Sure we all have those “Treat Yo Self” moments but not every trip should be like this. After all, you’ll want to have funds for future trips.
I always ask:
- Can I do this comfortably?
- Does this fit into my broader financial goals?
- Can I use points, credits, or smart planning without turning the trip into something it’s not?
In other words, loyalty programs and credit cards can help in the travel strategy, but only if they support the trip. Don’t go out of your way to somewhere you don’t care about to save $200. (I’ll talk more about this in a future blog post.)
If I can’t afford to enjoy a destination the way I want to experience it, I either adjust expectations or wait. There’s no prize for forcing a trip before you’re ready.
What Traveling With Intention Is Not
Traveling with intention doesn’t mean:
- Only going to “meaningful” or serious places
- Having a rigid itinerary
- Spending more money
- Avoiding spontaneous moments
- What my travel regrets have been
It simply means choosing destinations on purpose, instead of defaulting to trends, deals, or outside pressure.
Why This Is Important
Intentional travel means you’re more likely to come home energized, enjoy planning the trip beforehand, and hopefully not overschedule or overspend. Your trip should reflect who you are, not who you think you should be. Think about what will make you happy, not what your trip should be compared to others.
How I’ll Approach Travel on This Blog
In future blog posts, I’ll share:
- How I evaluate destinations beyond price alone
- How I balance excitement with logistics and budget
- How I use travel tools strategically after choosing a destination
- Why some trips are worth splurging on and others aren’t
My goal isn’t to convince you to go where I go.
It’s to help you choose better trips for yourself; trips that feel aligned, thoughtful, and genuinely exciting.
The best travel plans don’t always start with a deal. They start with intention.
