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Get A Head Start On Your Winter Getaway

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View of Bavaro beach, in Punta Cana, Dominican Republic. American travelers can find affordable flights to Punta Cana as more airlines add routes there.

Summer’s winding down, back-to-school sales are ramping up and family vacations have come and gone. Still, you're probably not thinking about winter yet, but now is the perfect time to start planning a winter getaway that won’t break the bank.

“Most people procrastinate their way into a really bad decision when it comes to trip planning,” said Rick Seaney, founder of travel deal site FareCompare.com. Don’t let that be you. Whether you want to design an early-December escape from dipping temperatures or a post-New Year’s jaunt, a little planning now will go a long way toward cutting costs -- and leaving you more cash to play with at your destination.

And choosing the right destination, experts say, is the key to an affordable escape. You probably won’t find the best deals if your heart is set on perennial favorites like Hawaii or Paris, says Anne Banas, editor of SmarterTravel.com. But there are plenty of other spots that offer great getaways without you having to give away too much green.

Beach bums, for example, would do well to look at the Caribbean, said George Hobica of Airfarewatchdog.com. “We’ve been monitoring airfare to various places for winter travel, and the Caribbean is particularly competitive because many carriers have added routes there,” he said.

Southwest recently launched routes to the Bahamas, Aruba and Jamaica, and service to Mexico and the Dominican Republic starts this fall. Both United and JetBlue have recently added flights to the Dominican Republic, as well. And often, when airlines add new routes, they advertise introductory fares, said Banas.

You may also want to consider destinations that may be a bit farther-flung but don’t cost much once you’re there, said Robert Firpo-Cappiello, executive editor of Budget Travel magazine. “You’ll pay $1,000 to fly to Vietnam, but once you’re on the ground, food and lodging are affordable, and the beaches are amazingly beautiful,” he said.

If you’d rather swish on the slopes than sit in the sand, the Mile High City is a pretty good bet. “We’re seeing great deals to Denver -- it’s still a very inexpensive place to fly,” said Hobica. That’s partly due to low-cost carrier Frontier Airlines, whose hub is there.

But if you’re really feeling adventurous, roll the dice when it comes to destination. Check out Hopper Flight Explorer, a tool that lets you see what destinations or regions are offering the best deals from your home airport during certain dates or times of the year. The site is aimed at travelers who want to choose a destination based on affordability, said Hopper’s chief data scientist Patrick Surry.

Once you’ve narrowed down some potential targets for your trip, the best way to score a deal is to sign up for alerts from both online travel agencies like Kayak.com and airlines and hotels themselves, said Banas. “Airlines offer flash sales all the time,” said Hobica, whose Airfarewatchdog site also lets consumers set up price alerts. “And prices fluctuate constantly.” Blink-and-you’ll-miss-them fares are not uncommon, so fare alerts do the monitoring for you. You should also subscribe to airline newsletters and follow them on Facebok and Twitter for deals, said Firpo-Capiello.

Keep in mind, adds Firpo-Capiello, that typically fares are at their lowest prices about two to three months before the travel dates. “Before that, airlines aren’t adjusting prices to demand or offering discounts,” he said.

A little flexibility when it comes to both timing and travel plans can save you a lot of scratch, adds Hobica. “I’ve seen round-trip flights from hub airports like Cleveland to Punta Cana in January and February for $240. The caveat is that some of these tickets require an overnight stay in Miami,” said Hobica. Flights without the layover can run you $700 per person. “So I look at it as a bonus stay. Normally, airlines would charge you for it, but you’re getting it for free,” he said. The cost of a hotel for one night, he said, is less than the difference in fares.

And timing flexibility may be most important of all. If you want to travel between December 20 and New Year’s, you should be prepared to pay premium prices. But if you’re willing to use your vacation days when everybody else isn’t, you’ll set yourself up for bargains.

“Between Thanksgiving and Christmas, and then again in January, places like Orlando see a drop from holiday crowds and you can get bargains on hotels,” said Firpo-Capiello. “New Orleans in January is less crowded and more affordable than it is closer to Mardi Gras. And many European cities are bargains in winter – you just have to put up with the chance of cold drizzle.”

The same is true for the days you travel. For example, everyone wants to hit the slopes on the weekend. But if you go midweek, said Banas, rates at hotels drop drastically.

Once you’ve booked your airfare, turn your attention to the hotel. You can wait a little longer to find savings on hotels, says Banas. And if you know where to look, you can score savings of up to 50 percent off. Deal sites like Jetsetter.com are a good place to start -- though you’ll find mostly non-refundable fares there. “But the best rates are always going to be non-refundable,” said Hobica. Meta search sites like Hipmunk.com and Getaroom.com, which features fast-expiring flash deals, should be your next stop.

But if you’d rather not commit to a non-refundable fare, book through Tingo.com. The site automatically scans your booked rate to see if a lower one is available. If the rate drops, the site automatically refunds you the difference.

Does all this sound like just too much work to save a little dough? There is another way, says Firpo-Capiello. “My favorite travel secret is that airlines and hotels do sell their seats and beds at rock-bottom prices. But they won’t tell you about it,” he said. “You’ll find those prices rolled into package deals that may also include some meals, tours, airport transfers, and sometimes cultural education as well.” You’ll find these deals at tour packagers like Gate 1, Monograms and Trafalgar, and also through the airlines themselves. 

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