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Why the Best Vacation Deals Are All About Timing

Choosing When and Where – Wisely

When Tom and Hedy Valledolmo booked a fall cruise, they didn't expect the ship to be filled with students.

Hedy, a retired teacher, was used to planning vacations around the academic calendar, so she thought the timing for this trip was perfect. She didn't know that local schools would be closed for a long weekend because of a teachers' convention and Election Day.

Booking at a non-prime travel time usually translates to smaller crowds, and better deals. But even expert travelers like the Valledolmos are sometimes surprised.

Here's what they, and other experts, recommend for maximizing your vacation days and dollars.

The Early, Intentional Traveler Gets the Deal

The Valledolmos, authors of “Something Bad Happen, Please!" – a self-help travel book – say they can't stress this enough: Book early. But they learned an equally important lesson after the fall cruise mishap: Do your homework.

That means being intentional in your travel planning, from checking the school calendar near your departure city to researching the destination's high-volume travel times.

Want to see Europe? The four-week holiday season in some countries there could limit availability to and around your desired destination, according to Laila Jensen, owner of Jensen Elite Travel in Brooklyn, N.Y.

“But in Scandinavian countries like Norway, traveling during their high season of June to August gives you the benefit of the Midnight Sun, which means longer days to enjoy the beautiful country," she says.

Working Around the Weather

Weather is impossible to pin down, but knowing as much as you can about a destination's typical patterns is wise.

Theme parks in September may be ideal for shorter lines, better rates, and beating the summer heat, says Jensen, but you'll have to pack ponchos for daily rain showers in some areas. Similarly, she doesn't recommend a Caribbean destination wedding or honeymoon in September or October, the peak months of hurricane season. Rates may be better, but you risk having to cancel entirely, leave early, or take shelter in country. And of course if you want to see fall foliage in an autumn haven like The Berkshires, timing is everything. So researching the seasons and booking well in advance is crucial.

You Can (Often) Cancel

Life, like the weather, is unpredictable. But that's no excuse for missing the great deals you get by booking early. The Valledolmos have already booked a cruise for next New Year's Eve, and by doing so, they got their first-choice cabin. Jensen says that, as a travel agent, she can negotiate for the best rates when clients plan ahead.

Depending on how you book the trip, you can usually get your money back if you can't make it. “Many of the cruises we book through our favorite travel site can be cancelled 30-60 days before the trip and we still get all of our money, deposits included, refunded," says Hedy.

If you're concerned about things changing, consider travel insurance or work directly with online or brick-and-mortar agencies that have a flexible cancellation policy.

Score Savings By Being Social

Not the plan-ahead, book-early type? That's fine, especially if you're the tech-savvy social type. Seasoned travel writer Aly Walansky uses mobile apps – she recommends Hotel Tonight – to find money-saving travel deals when time is of the essence.

She also suggests following travel writers, experts, and airlines and other travel companies on Twitter. "You can find out about last-minute hotel, cruise, and airfare deals just by being social," she says.

Fly on Lighter Days for Less

It also pays to be smart with scheduling, says Jensen. "Tuesday and Wednesday are the least expensive days to travel, because most business travelers come in on a Monday and leave on a Friday," she says. And for additional savings, grab a coffee, because early morning flights often offer the lowest rates, she says.

Travel flexibility helps, adds Walansky. "Time of day, day of week, and the airports you're flying into or out of can all spell major deals if you're flexible with your time."

Dodge delays, avoid crowds, and seize the deals: Smart travel that's better for your bank statement and blood pressure is all in the timing.

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