We live in the Pacific Northwest, so by February, deep enough into winter that the season has stopped feeling new, warmth stops being a preference and the cold becomes something that needs correction. The trouble is doing that from the PNW in February isn’t especially convenient. The obvious short-haul answers, Hawaii, Mexico, Costa Rica, Caribbean, are the obvious answers for a reason. We’ve leaned on all of them more than once. When we go further for something that feels like a special occasion, the extra flight time starts competing with how much time we have once we land, especially since our business doesn’t pause for the trip. We’ve made that trade too though: Thailand, Singapore, New Zealand, the South Pacific. Each one solved the challenge once and then joined the list of places we’ve already been.

It used to be a little simpler, before I was running a business built around travel. In the corporate world, February didn’t carry anything especially demanding for either of us professionally; we were mostly just working around whatever PTO balance we had. Now I’m on the other side of that calendar. February is right in the middle of what is known as “wave season”, one of the busiest booking windows of the year and travel providers often run some of their steepest promotions, so it’s genuinely one of the busiest travel months. And because my birthday falls in February, as does our anniversary, the month demands an answer to the “where” question regardless of that. The “when” is fixed, the where resets every year. Some years that comes easily, some years it doesn’t. Next February, we’re headed to Vietnam and Cambodia, but more on that in a future newsletter.

The same logic holds even without a birthday or anniversary. A week in June doesn’t send you to Colorado for skiing, it sends you to Chile or New Zealand. A calm, warm-water beach week doesn’t happen in the Mediterranean in January. Usually, one of the two, the date or the kind of trip, gets to lead, and the other one follows.

There are trips that skip that decision entirely, because the experience itself sets both variables at once: an Antarctica expedition only sails when the Southern Hemisphere’s summer breaks up the pack ice, roughly November through March, and chasing the Aurora Borealis only works in the long, dark nights a Northern Hemisphere summer can’t give you. Neither is really a choice between two variables. The destination and date arrive as one decision.

On our last several trips to Europe in the summer, the destination was never what was actually up for debate. However, Rome hit 100 degrees when we were there in 2019. London was miserably hot last July, and Athens cleared 100 in early June last summer. None of that was the historical norm for those places, whatever “normal” means for European summer anymore. Personally, I don’t do well in extreme heat: it cuts the walking and closes off access to what I typically build my trips around—wandering aimlessly and enjoying outdoor cafe culture. Europe is warming faster than any other continent, and the kind of summer that used to mean dependable Mediterranean weather increasingly comes with a real chance of a serious heatwave, so we’ve started shifting into spring and fall instead, keeping the destination and moving the date.

A couple I worked with earlier this year ran into my annual dilemma in reverse: the “where” was fixed, the “when” was somewhat open. They wanted to go to Thailand for their delayed honeymoon, Koh Samui specifically. Their first target was October and that is one of the months where the location within Thailand matters quite a bit. Koh Samui sits on the east side in the Gulf of Thailand, and is the beginning of monsoon season. Rainfall climbs through October and keeps climbing into a wet November. The opposite side of the country, on the Andaman coast, Phuket and Krabi and the islands near them, runs in the reverse pattern in that same window. They are coming off of their rainy stretch rather than heading into it. Neither coast is perfect weather for October. My clients ultimately ended up moving their date and they were then able to comfortably plan for Koh Samui in one of the most beautiful weather months: February.

Not every trip resolves that cleanly. My own February search continues to challenge me every year. Most of the time, one of the two constraints: “when” or “where”, has to give a little so the other can hold. Knowing early which one has room to move is a critical piece of information for planning.

If you’re new to the blog and you want to see how the “where” got decided for my upcoming trip to Spain, given the “when” was fixed, it’s live now on the blog here: https://mavencurated.com/2026/09/03/from-vibe-to-five-cities/