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Your Guide to Vacation Planning

Older man in wetsuit surfing a wave at sunset

Alistair Berg / Getty Images

Stop stockpiling time off. Plan a vacation.

Too many of us leave leisure time on the table, according to the U.S. Travel Association. Every year more than half of Americans fail to use all their time off, creating a stockpile of 662 million unused vacation days. Think of all the mountains not climbed, the wineries not toured and the beaches not sunbathed on. This year it’s time to do something different.

One of the chief reasons for our national vacation deficit is that people don’t take time to plan. But the middle of winter — now — is a perfect time to tackle the chore. Research shows that those who take the time to plan are more likely to use all their vacation days and to take longer trips.

And think of the payoff: in just a few months, when you find yourself tracking elephants on safari, dazzled by the lights of Broadway or ordering cocktails on a cruise.

Here are some trip planning basics.

Quick getaway

There’s no shame if you only have time for a long weekend. But for a short trip, planning is still important, as you want to make every minute count.

Consider this time frame perfect for a romantic escape, a big-city culture trip or a beach holiday. A few days is also ideal for breaks at a lake, mountain or theme park. If your heart’s set on trying a specific restaurant or signing up for a special activity, you’ll want to book it ahead of time, because with just a few days, there’s no margin for error.

Even if you have the budget to travel cross-country, it’s wise to consider a nearby or familiar destination, perhaps one that can be reached by car or a short train trip. That way you’re less likely to get stuck in airport lines or be delayed by bad weather, which could blow your whole vacation.

Unless you’re aiming for a holiday weekend or another popular time, you can comfortably schedule a journey like this from one month to 60 days out. Some online booking sites specialize in last-minute getaways and can offer bargains even closer to your departure date, says Michele O'Connor, a trip planner and operator of the Fun in Key West (funinkeywest.com) website. “I wouldn't count on those as an absolute way to book a room or flight, but if you are under the 30-day window, you may snatch a great deal.”

Weeklong vacation

This type of escape will take more time to pull together, so start planning six to eight months before leaving home.

If you’re hoping to have friends or family join you, allow time to coordinate schedules and to discover what your travel companions want to do. If someone has her heart set on visiting a famous museum or taking a day trip to a historic site, you’ll want to know that before you’ve nailed down the details. If nothing else, don’t make concrete plans (or put down a deposit on a house rental) until everyone has committed. Also, you may want to consider travel insurance, given the time and money commitment.

A cruise can be a perfect fit for a weeklong trip, and January and February land in the middle of “wave season,” when many cruise lines offer discounts. After booking a trip, most of your work will be done, since cruises make it easy to arrange shore excursions and other activities. It makes sense to use a travel agent for this type of trip, and if your group is large enough, you can often get a discount.

But a week is also long enough to try something new or to add some adventure to your outing, says Elizabeth Avery, author of several travel planning guides. “Take four days of ski or scuba lessons. Travel to the Caribbean. Have a French holiday in Quebec,” she suggests.

A man standing by a campfire near a camper van on a wide expanse of a valley at dusk

Woods Wheatcroft / Gallery Stock

The sunset lights up an Oregon mountain as a traveler enjoys a campfire outside his camper.

Bucket-list trip

If you’re planning a getaway of a lifetime, it’s going to take some work. You’ll want to start more than a year in advance because of the myriad details. And since you’ll likely be investing thousands of dollars in the adventure, there’s more at stake. Expect to work with a travel agent or planner, particularly someone who specializes in the region you’re visiting or the type of trip you’re taking. Make sure to read online reviews, and check out the reliability of tour operators.

Also, remember that trip planning includes not only arranging transportation, lodging and activities but also taking care of medical and financial considerations and paperwork. Do you need immunizations? How will you pay bills if you are gone for several weeks? Are special visas or permits required? Do you need special medical, evacuation or trip insurance? All these questions should be on your planning list.

This type of trip could include trekking in Nepal, visiting Machu Picchu or renting an RV to follow Historic Route 66 across the West. But whatever you decide, make sure to pick your travel companions carefully. You’re going to be spending a lot of time together, after all.

Finally, don’t overdo it. “Remember that the more you see the less you'll actually ‘see,’ ” says Sean P. Finelli of the Roman Guy (theromanguy.com), an Italy travel planning service. “You need to stop and smell the Italian sunflowers. Don’t cram so much in just to cross it off the bucket list.”

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