Travel Advice: Cheap Winter Vacation In Four Easy Steps

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Heard On The Larry Meiller Show

Larry Meiller finds out how to plan a cheap winter vacation in four easy steps. Plus, answers to listeners’ travel questions.

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  • Tips For Planning Winter Getaways

    Winter started early this year in Wisconsin, and it’s been pretty unrelenting so far. Between the ice, snow and frigid temperatures, a lot of people are dreaming about getting away for at least a short break.

    Rick Seaney, the CEO and co-founder of, has great advice to share for those looking to get away, taken from a recent article on FareCompare titled, “How to Plan A Cheap Winter Vacation In Four Easy Steps.”

    Here are Seaney’s tips:

    Step One: Choose The Right Destination

    Seaney said that the “right” destination really depends on whether one is looking for cold weather, for winter sports, or warm weather to get out of the cold. And of course, budget will help determine the right destination and how long to stay.

    Tips from the article are:

    • The Caribbean will be pricy but there are still a few bargains including Puerto Rico, the Bahamas and even deals to Bermuda (especially from New York).
    • Flights to Florida are usually much cheaper and best destinations include Fort Lauderdale, Miami, Orlando and Tampa.
    • Skiers should look at two generally cheap cities: Boston, which offers easy access to New England resorts or Denver, gateway to all that excellent skiing in the Rockies.

    Step Two: Fly When It’s Cheap

    Seaney said, “If you’re trying to go in the next couple weeks, if you’re a procrastinator or what not, what you want to do is look at package deals because they actually pre-set some of those rates.”

    But if it’s a little further out, maybe the end of February or so, Seaney said that there are more options than just those packages.

    Tips from the article: January and early February offer some of the best domestic deals of the year. Make it even cheaper by flying midweek (Tuesdays and Wednesdays). Saturdays can be cheap, too. Tip: Avoid flights on Fridays and Sunday, when you’ll typically pay top dollar.

    Step Three: Look At Package Deals

    Speaking of package deals, Seaney said that while Americans don’t tend to buy them often, Europeans buy them frequently.

    Seaney reiterated that packages are best for trips out just a few weeks.

    “So, it’s weekenders, packages on weekends, they can discount the price of the air and the hotel and you don’t know it, so that’s why the airlines are willing to do a little bit of discounting,” he said.

    Seaney warns that buying a package a month or more in advance doesn’t equal much in savings.

    Tips from the article: Several airlines offer packages providing flight plus hotels (and sometimes even rental cars). Look at these options carefully, he said. The hotels offered might be more than a person would be willing to pay normally but the overall discounting may put the total package within the budget. Maybe the person is better off making separate reservations. Only that person can say for sure.

    Step Four: Book Now

    Seaney said that for a number of factors, there is no longer an advantage to waiting to book your ticket.

    “In today’s environment, where you have no empty middle seats, the price of oil is near $100 a barrel, airlines are making record profits, prices don’t tend to drop as you get closer to your date. It’s just a fact of life,” he said.

    On top of that, Seaney added, “If you’re inside of 14 days before travel, airlines are going to treat as though your boss is paying for your ticket and can afford a lot more.”

    Tips from the article: Some airfare deals require an advance purchase of from seven to 21 days before departure. Fly sooner rather than later because once the President’s Day weekend comes along, fares start shooting up in anticipation of spring break.

Episode Credits

  • Larry Meiller Host
  • Judith Siers-Poisson Producer
  • Rick Seaney Guest