07/02/2014 12:53 pm ET Updated Sep 01, 2014

Feeling a Bit "Off?" Travel During the Off Season

I have a friend from Wales who, several years back, wanted his first trip to the United States to be perfect. He settled on a city, New York. He researched the hotels, the sites to see, the restaurants to hit. He did all of this with the idea of coming in July, particularly for Independence Day, since he wanted to experience a genuinely American holiday.

Never again.

It's not that he didn't have a good time. It's not that he was a Brit and the 4th of July is a holiday commemorating when America gave Britain the boot. It was because no one told this northern European what New York is like in July. The man, for whom 80º F qualifies as an extinction-level heat wave, came smack in the middle of "Bermuda High" season, when 100º F is par for the course. He still visits, of course. In October.

So much for traveling in-season. He found out the hard way, and the way a lot of people find out, that just because you are traveling to a destination during "the season" doesn't necessarily guarantee a good time. Safely ensconced back in Wales -- which, shall we say, is not known for its balmy weather -- he has since become one of those travelers beholden to a new rule of travel: Screw "the season."

Of course, traveling in the off-season is not a secret. People have been doing it for years, and they take stride the caveats; some places are going to be busy no matter when you go. Paris, New York, Bangkok -- the top "world cities" are always going to be perennially crowded. More over, these hardy folk know the off-season is just that for a reason. As it will be winter, New York will be cold; as it will be summer, Bangkok will be broiling (and the monsoon will be in high gear). But rates will be lower and the crowds less dense, and since New York is the exact same city whatever time of the year, what's the big deal about packing a parka?

It is also true that often the off-season is off for a reason; just ask Aspen or Provincetown. But then there are places that are absolutely serviceable in the off-season that are downright empty. How many of us have muttered aloud, "I want to go there when no one else is there"? So why don't we?

A good example of a place being a victim of is own "season success" is Hvar Island, off the coast of Croatia. This country opposite Italy on the Adriatic Sea is the new darling of the glitterati, and Hvar Town in particular feels the love during its canonical season, June, July, and August. But as is so often the case, especially with glitterati hot spots, Hvar is empty the rest of the year, as if the Travel Gods waved a wand and all the plusses that make Hvar a destination vanish. Au contraire.

Hvar Town is a perfect example how the on-season can the one time to not go to a place. So many people descend on the island--and it's a small place--that the result is bumper-to-bumper pedestrian traffic simply not designed to absorb such a crowd. All the things that make the towns of Hvar Island charming, the cozy squares and narrow lanes (like, as wide as your shoulders), become all the things that make it a madhouse from June to August. Correspondingly, the prices go up, the lines get long, and tempers get short. But from April to May and again in September, a span of time where the temperature is still shorts-worthy and you can wander the medieval streets of Hvar and not feel like you are in sardine tin. You get the genuine, intimate experience of being in another country and culture. More, the people of Hvar are far more friendly, since they are not dealing with drunken foreigners 24 hours a day.

Hvar has company. I recently spoke with Jesús González of the JW Marriott in Gaunacaste, Costa Rica. This is one of Central America's great resorts, splayed out over several hundred acres on the Pacific coast. Its season is the winter months of the Northern Hemisphere, but come the Northern summer and poof! The property is a ghost town, as visitors flee the heat.

González tells me this often stems from a general ignorance of summer in Costa Rica, a nation with low lands, mountains, and everything in between. The Caribbean side of the country, true, is a steam bath (and not just in summer), but the Pacific side is much drier and cooler. Summer in this section the country is only marginally hotter, perhaps by 10 degrees Fahrenheit, from winter.