"Cost usually plays into the decision on where we go depending on how much it's going to cost to get there," said Richards.
She is a fan of something called "shoulder season." It is the short time that falls between low and high travel season.
"You can always get a better deal during the shoulder season," said Richards. "You can always find the destinations to be less crowded."
It hits at different times for different places. Travel and Leisure Magazine's Sarah Kantrowitz says finding great destination deals depends on when you plan to get away.
In January, Florida is one of her top picks since hotels and beaches are still fairly empty. Skipping ahead to March, Kantrowitz recommends looking south of the border.
"Rio de Janeiro, Brazil is a fabulous place to travel to in March. This is because it's just after Carnival and you're going to find hotel rates that are about 60 percent off the average rate," said Kantrowitz.
The Caribbean is hot for April, but so are many European cities.
"We're particularly excited about Scotland in Edinburgh and in Glasgow you can visit all sorts of cultural attractions," said Kantrowitz.
In May, it's all about the Mediterranean, where prices are about 20 percent lower than in the summer plus great cruise deals too. And if you're already planning for September you may want to head to the islands of Hawaii.
"You might consider Hawaii where the water is still very warm and the crowds decrease after Labor Day," said Kantrowitz.
By the end of the year, decide if you want to go warm or cold. Travel and Leisure suggests the Riviera Maya in Mexico for November. But December's pick will have you packing a parka. Kantrowitz says there are shoulder season specials in the Rockies.
"Colorado in particular is a perfect destination in early December and they're known for having lots of different mountainous peaks such as Vail, Beaver Creek and Aspen," said Kantrowitz.
That's perfect for Cindy Richards. While she adores warm weather trips, she admits she tends to like the cold weather as well.
"Many of my shoulder season trips have been actually to colder weather climates," said Richards.
Places that cater to families, like Hawaii and Florida, offer fewer deals during the summer months, when kids are off from school.