How to Choose Where to Go Next (When I Want to Go Everywhere)

Emily Whitaker
Feb 2
3 min read

How I Choose Where to Go Next

When I Want to Go Everywhere

Instead of throwing darts- try this.

If you’ve ever found yourself with 37 tabs open—flights to Italy, a reel about Japan, someone’s “hidden gems” list in Mexico City, and a random safari video you can’t stop watching—welcome. This is me on a Tuesday.

I love the dreaming stage of travel planning… but choosing the next destination can be weirdly hard. Not because I don’t have ideas (I have too many), but because I want the trip to match my life, my energy, and the season I’m in—not just what looks good online.

So here’s how I actually decide where to go next. It’s part practical, part intuition, and fully built around one goal: I want to land excited—not stressed.

Step 1: I start with the season and weather

Before I fall in love with a destination, I ask: What is it like there when I can actually go?Because the truth is, the “best” place isn’t best if it’s rainy season, extreme heat, or smoke season (I'm looking at you Chiang Mai, Thailand (burn season February-April).

I look at:

average temps (I like comfortable exploring weather)
rainy/monsoon seasons
how daylight hours will feel (short days can change the vibe)

Weather isn’t everything, but it sets the tone for the whole trip. I’m not trying to spend a week hiding in my hotel because I didn’t check the basics.

Step 2: I decide what kind of trip I need

This is the part that changed everything for me: I don’t plan trips based on what sounds impressive. I plan trips based on what the goal of the trip is.

So I ask myself:

Do I need rest or adventure?
Do I want a place that’s easy (walkable, simple transport) or a little more challenging?
Do I want nature, culture, food, shopping, or a mix?
Do I want to be around people—or do I want to disappear a little?

Sometimes I want museums and cute cafés. Sometimes I want mountains. Sometimes I want to wander and take photos with no schedule. The point is: the right trip fits my current energy.

Step 3: I check my comfort level (especially when I’m going solo)

When I’m traveling solo, comfort and safety matter even more—not because I’m afraid, but because I want to feel confident.

I think about:

walkability (can I enjoy my days without complicated logistics?)
the vibe at night (would I feel okay grabbing dinner alone?)
transportation (is it simple to get from airport to hotel and around town?)
language barrier (am I okay navigating this right now?)

This step helps me choose trips that feel empowering instead of draining.

Step 4: I price-check the “real trip,” not the fantasy trip

I’ve learned this the hard way: the cheap flight doesn’t matter if the destination is expensive once you arrive.

So I do a quick reality check:

flight + local transportation
lodging that matches my comfort level - I stay a mid-range hotels. Not hostels, but not luxury travel.
food (will I be eating out most meals?)
2–3 activities I definitely want to do- I try to always go on a food tour and take a cooking class.
a cushion (because I like to travel without financial anxiety)

If the trip feels tight, I either shorten it, pick a different city, or save it for later. Dreaming is free—but I want the actual trip to feel good while I’m there.

Step 5: I use a simple “top 3” filter

When I can’t decide, I narrow to three options and choose based on a quick scorecard.

I ask:

Which one fits the season best?
Which one fits my energy and schedule best?
Which one makes me feel the most excited right now?

That last one matters. Because sometimes the practical choice is obvious—and sometimes your heart is quietly pointing at the one you keep coming back to.

Step 6: I listen for the “pull”

This part is hard to explain, but I know it when I feel it. There are destinations I like, and then there are destinations that feel like they’re calling my name.

If I keep saving videos about it… if I’m already imagining the mornings there… if I can picture myself walking around with my camera and feeling alive… that’s usually my answer.

My rule: pick the trip that makes your life feel bigger

Sometimes choosing where to go next is as simple as asking:

What kind of experience would help me feel more like myself?

And then giving yourself permission to choose that.