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7 Tips on When to Take That Vacation

anyaberkut / iStock / thinkstock.com

anyaberkut / iStock / thinkstock.com

Anytime is a good time for a vacation—one sounds good right about now—but some months, or days even, are better than others. Price, weather and crowds come into the equation when deciding when to go. Here are a few tips we hope will help.

Pick the Right Days
When flying over the holidays the day before and the day after are the busiest. The holiday itself is a good day as far as avoiding crowds but then that defeats the purpose doesn’t it. Usually, except on a weekend, driving on the 4th of July is a breeze because everyone else is barbecuing, drinking, and watching fireworks; in my neighborhood usually all at the same time.

Early to bed and Early to Rise
Fly first thing in the morning to avoid delays. The later in the day the more likely there could be a delay. Redeyes (late night or overnight flights) are almost always less crowded, but you will feel like a zombie when you arrive and that’s even without alcohol being involved.

Where You Layover Counts
Also be aware of certain airports. Every time I’ve flown through Dallas in the summer, or Chicago or New York in the winter, I’ve been delayed. While I enjoy the fine-dining experience of airport food as much as the next guy, hanging around a terminal gets a bit old. On that subject, just who the heck is the sado-masochistic jerk who designs airport seating? It’s probably the same guy who designed the airplane seats.

Couldn’t Stand the Weather
Montana is lovely in the summer; in the winter, not so much. That is unless you’re a skier but otherwise a rule of thumb is or should be, go north in the summer and south in the winter. Mexico and other points south like the Caribbean are brutally hot and humid in the summer. Like in most places, spring and fall are pleasant and sometimes cheaper though. Unless you plan on playing beer-pong all night long, you may want to avoid Mexico during spring break.

Schools Out for Summer
If you’re wanting to avoid kids on a cruise and let’s face it, who isn’t, Cruises are a good bet right after school starts in the fall. Nothing against kids, heck, we were all kids once, but listening to a bunch of screamers in the pool, getting run over in the hallways, and having Coke spilled on you in the buffet is not my cup of tea. If it is, try a Disney cruise and leave the rest of us to do our drinking in peace.

Money is an object
If money is an object, the best time to travel to Caribbean resorts is early fall (Sept, Oct), partly due to hurricane season. You do take a risk on the weather, but the payoff, besides the no-kids part mentioned earlier is lower prices and smaller crowds. Late spring (April and May) are also cheaper in the islands as it is quieter there right before the big summer season price hikes. If you want to visit a ski-resort/mountain town, try late April into May. There is absolutely no one there and prices are ridiculously low. There’s a reason for that: it’s called mud season and all the residents are in the Caribbean.

I’m Really Not a People Person
Most vacations are also social events. I like being around lots of people, I just don’t care to have to actually talk to them. If this is you, pick the off-season for wherever you’re going; the mountains in May, the Caribbean in November, and Europe in winter. You won’t run into as many people, you may not have as much fun, but you’ll probably see me there; just don’t talk to me.


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