In my opinion when you travel has as much bearing on your vacation as where you travel to. Here in the US the "big" season to travel is June-July-August, when the kids are out of school. That is also when prices are highest, popular locations are at a premium and crowds are heaviest.
We typically travel during low or shoulder season. At the moment we don't have school schedules to contend with but I can honestly say that we won't hesitate to pull the girls out of school to take them somewhere (we will, of course, make sure they aren't missing anything important that can't be made up).
As an example: We will be in Ireland the first week of March. Technically this is low season; "shoulder season", between high & low season" begins the end of March through early May. However, March is one of the driest months of the year and the temperatures are typically in the mid-40's (much warmer than they are here!)
I found an article of tips for shoulder season travelby Tim Leffel, MSNBC's travel columnist. (I have added hyper links and my additional thoughts are italicized)
1. Most guidebooks and country-specific Web sites have a "When to Go" section that describes the ideal time to visit an area, as well as the worst time. Between those two seasons, you'll get the best bang for your travel buck. Be sure to do your research, though. You don't want to arrive and find that places you wanted to see and amusements you wanted to enjoy are closed for the season.
2. Airfare prediction sites (such as FareCompare.com and Farecast.com) can give you a rough idea of how flight prices fluctuate and will also show you the best deals from your own airport in any given month.
3. Most rental homes and villas clearly list prices by season. Just moving your planned vacation two weeks in one direction or another can save you a bundle. Moving it a month or two can cut the price in half.
4. Travel sites that move unsold inventory can present fantastic shoulder-season deals when hotels struggle to fill rooms. Try Hotwire.com, Priceline.com and SkyAuction.com — or just pick a place and call direct to start bargaining. If it's a last-minute trip, try LastMinuteTravel.com to get a cheap package deal. A site that I have used and had a great trip with is GoToday.com. And don't overlook a good travel agent. My agent has found better deals for me 9 times out of 10 than I found online.
5. Consider where the crowds are going, then plot a different course. You can ski in Chile or Argentina in July, for instance, or visit the tulip fields of Holland or the green hills of Ireland in the spring — before much-higher summer airfares kick in. Spend the busy summer break in a U.S. destination that's off the tourist radar, or in a lesser-known part of a nearby country like Canada, Mexico or Guatemala. Or, take an African safari — June to August is actually the shoulder season in Kenya and Tanzania.
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