Delayed gratification: Traveling during the off-season

I'd love to be on an island right now. Or a mountain. Or anyplace not gloppy.

Instead, I'm sitting in a Midwest coffee shop, 851 feet above sea level, watching another greasy winter rain goopify what little snow we've had this year. 

I know there are people freediving technicolor reefs this very second. I know there are people riding hidden glades of powder. I know these things because I can see them from my rigid chair. I can see every one of their posts and boasts and aprés toasts.  Based on their social feeds, it seems they're having a gangbuster time. And they really want me to know about it. Bastards.

But I know something they don't. See, I'm not just sitting here like some maroon. Although I might look like a man without a plan (and yes, largely I am), when it comes to travel I've got plans for miles.

What most people consider peak travel season (aka right now), for me is peak planning season. So it came to be that I spent a good chunk of this past weekend trawling trip advisor, checking frequent flier miles, and reviewing the fishing regulations of various island nations. Sunday was gloomy AF here. But I was a million miles away – the Lesser Antilles, Central America, the Indochinese peninsula. The online investigations alone made for a good day. The fact that it all culminated in flight confirmations is the best part. 

An emergency gloom-reducing winter trip out of Dodge? Nope. As per usual, we decided on a trip to the tropics in the dead of summer. St. John to be exact. Why? The average temperature on St. John in July is 82.3 degrees F. Lovely! Of course, the average temperature in Madison in July (where we live) is 82.1 degrees F. Also lovely!

So what's the point? The off-season rules, that's the point. The equator in June, the Wasatch Range in August, Berlin in any month that doesn't end in "fest." It's a contrarian approach to travel, a zig on the zaggers that, to my way of thinking anyway, can pay off hugely.

Obviously, travel's cheaper in the off-season. That goes without saying. (Although I said it nonetheless. Sorry, I'm a sayer. A talker. I do rattle on.) The upside is that the less money you spend traveling to stuff, and sleeping near the stuff, the more money you can put toward doing stuff. Doing stuff is the whole point.

The other upside to the off-season, of course, is less crowds. I don't like crowds nor most of the people they're made of. That's true always. But when traveling, it's worse because most of the people in a crowd aren't from the place I went to see. Most of them, it seems, were cruise-shipped-in directly from the Kenosha, Wisconsin outlet mall. This kills the vibe of a place something awful. During peak season the locals (true locals and expats alike) are either in hustle or hide-out mode – doing their time until the clown car finally loads up and casts off the lines.

If you're interested in hanging out in a rum shop shooting the tropical breeze over a bowl of callaloo, you're gonna need the off season for that friend-o.

Ditto if you're looking for a little more open-endedness in your travel. We've done several summertime trips to the West Indies where we booked our lodging as we went along. We've done the same in the remote corners of the Rockies. I wouldn't recommend winging it in Maui, regardless of season. But combine off-season with off-the-beaten-path and you're free to play the days as they lie.

Holy moly. What's the point of this extended ramble? I'm curious about that too! All I know for sure is that it's crummy where I'm sitting right now. And it's nice where I'm going in July. Clearly I have some time to kill.