Favorite Trip Planning Tools: Sites that tell you where to go and when to go

There are two types of vacations: 1) The I-don’t-care-where-I-go-I-just-need-to-get-the-heck-out-of-here, and 2) the I-really-want-to-go-to-there vacation. How do you get started on your planning? Each type requires a slightly different approach. Here are a few tools that help.

Know where you want to go, but not sure when is the best time?
If you have your mind made up about a destination but aren’t sure when to go, this is the site to use.

Does anyone about this awesome little tool? Buried at the bottom of Hotwire’s homepage, a tiny button takes you to Hotwire’s Trip Starter, and I don’t know of another site that aggregates this kind of information for travelers in one place.

Plug in your starting point and your destination, and Trip Starter displays a chart showing you when hotels and airfare are cheapest, based on historical averages. Scroll down a wee bit and it shows you monthly averages for temperature and precipitation. In the right-hand column, they sum up for you the cheapest time to go and the best time to go.

Weather.com has monthly averages too, but good luck navigating to it—their website has tons of decent info that’s impossible to find. Your best bet is to Google “Denver annual weather” and look for the Weather.com link in the search results, shown below.

Once you’ve done a little homework on Trip Starter, ItaSoftware.com offers a matrix that will spit out the cheapest airfare for your destination based on a month-long window and the number of nights you want to stay.

Know when you want to travel, but not sure where?

There are a few sites where you can specify your departure city, month of travel, and budget, and it’ll spit out airfares to any destinations that match. Of the ones I’m aware of, Kayak Explore has the best options for refining your search. In addition to the parameters noted above, you can search by season rather than by month (ie, Fall 2013), what kind of weather you want, and the types of activities you’re interested in (ie, beach).

Check out the Where-to-Go Getaway Map on Farecompare.com, too. You plug in your starting destination, the month you want to travel, and your budget per person for airfare, and the map displays rates for destinations all over the world.

At airfarewatchdog.com, you can also search for fares from your departure city. No pretty maps, and the date selection tool isn’t as straightforward, but they come up with some sales that other airfare sites don’t find, so it’s definitely worth a look.

So what are your favorite planning tools?

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