Make Your Next Trip Extraordinary

How to Maximize Your Vacations This Year

by Wendy Perrin | December 22, 2019

January is a great time to look at the year ahead and plot out where in the world it might take you. Each January, I sit down with a calendar and approach my vacation planning the same way I approach my budget planning, so as to maximize my travel dollar, time, and enjoyment. Here’s how you too can get the accommodations and experiences you really want, at the best prices, rather than settling for what’s left over after everyone else has booked their trips:

Grab your calendar and look at when the long holiday weekends fall.

Check the dates for Presidents’ Day, Easter, Memorial Day, and so on. These dates will dictate either when to travel or when not to, depending on whether you’re tied to a work schedule and/or have kids in school. If you are holiday-schedule-bound, ask yourself where you could add one or more days onto the start or end of a holiday weekend. If you’re not tied to a holiday schedule, by all means avoid traveling at these times. Instead, travel between these holidays, to take advantage of lower airfares, lower hotel rates, and fewer tourists.

Predict what weather-related escapes you will need when.

I know, for instance, that when the February school break arrives each year, my husband will need a snow-free getaway or we will all go nuts. I also know that, in the dog days of August, I crave someplace cool—or, at least, cooler than home. I’ve learned that that doesn’t necessarily mean a higher latitude. While my family has adored our August escapes to cooler climes (Newfoundland, British Columbia, London, Iceland), I’ve also found that southerly places can provide first-rate relief as long as there’s an ocean breeze (Virginia’s Chesapeake Bay; the beaches of Charleston, South Carolina; St. Simon’s Island, Georgia; Playa del Carmen, Mexico).

Consider what destinations are in “shoulder season” at those times when you can travel.

Shoulder season is that time between peak and low seasons when you usually get the most value for your dollar because the weather is good yet prices are lower and tourists fewer than in peak season. Our Where To Go When series and Ideal Islands for Each Month of the Year will give you plenty of shoulder-season ideas for those windows of time when you have availability. If you’re specifically seeking destinations that are a great value during major school holidays, see Unexpected Spring Break Vacation Ideas and Unexpected Holiday Travel Ideas for Christmas and New Year’s. My family once spent a phenomenal February school break in sunny Andalusia, Spain, for example, and we once spent a festive Thanksgiving exploring Central Europe’s Christmas markets on a European river cruise.

Know where your money will go furthest internationally.

It’s always smart to factor exchange rates into your decisions. Airline routes and fares also determine trip cost and convenience, of course. If you live in or near a major U.S. hub, check out these New Flight Routes That Could Improve Your 2020 Travels.

Set up low-airfare alerts.

Now that you have a sense of which places interest you most for the time slots you’ve got available, pinpoint the right time to buy your airline tickets. There are websites that will notify you by email when fares drop on specific routes or specific dates or both. (I like the price-alert tools at FareCompare, Kayak, and AirfareWatchdog). If you’re considering a long-weekend getaway and can take only two days off work, remember that it’s usually less expensive to fly on a Saturday and return on a Tuesday than to fly on a Thursday and return on a Sunday.

Know when to book the rest of your trip.

Depending on the trip, airfare may not be the only component that should be booked well in advance. Say you want to go to the Netherlands to see the legendary springtime tulips. For the most local color, it’s smart to be there on April 27 for King’s Day, the festive national holiday. And if you’re going to Amsterdam, visiting the Anne Frank House is a must. Tickets for that become available two months ahead and sell out quickly. If you outline your Netherlands itinerary in January, you’ll know which dates you want to go to the Keukenhof Gardens and the Anne Frank House, and you can snap up tickets as soon as they become available in February. See our What To Book When series, where we recommend the best times to book trips to specific destinations.

Pinpoint the right destination specialist.

If your end goal is the most rewarding travel experience possible, the smartest way to approach booking your trip—the way that will deliver the greatest value for money—is not to book all the various components (accommodations, activities, transportation, hard-to-get tickets, special guided experiences) piecemeal but, rather, to hand the whole thing over to the right destination specialist who knows all the insider tips and tricks in the place where you’re headed.

If you are mulling over a vacation that is a resort stay, book it now, as long as you can cancel with no fee.

When you think you might need a room at an island resort, or at a popular resort in peak season, reserve your spot, as long as there’s no cancellation penalty. The more in-demand your destination, the less supply (airline service, hotel infrastructure) you will find.  Islands in particular have limited flights and limited hotel options, leading to high prices and sold-out conditions. So that you’re not shut out, book a spot but be sure to mark on your calendar the date when you need to cancel in order to avoid paying any fee.

If the resort you want is fully booked, ask when cancellation penalties set in for the dates you want.

First, call the resort directly (not a website, not the 800 number) and ask whether it’s truly sold out (the resort itself might have different inventory) and whether there’s a waitlist. Then, find out when the cancellation fee sets in for people who are booked on the day you’d like to arrive. Mark your calendar to call the hotel the day before that fee sets in: That’s when other people will be cancelling and you can try to scoop up a room that has just opened up. Or, easier and likely more effective, contact the right destination specialist (see #7) and have them work their magic via their local hotel connections.

Start thinking about Christmas/New Year’s now.

I’m not kidding. It’s the most in-demand travel period of the year, with peak prices and minimum-stay restrictions at popular beach and ski locations. Some of Hawaii’s top resorts, for example, are already fully booked for the December 2020 holiday period. These resorts save their rooms for loyal guests who return year after year. If those returning guests should cancel—and sometimes they do when deposits come due in March or April—then a few rooms may open up to new travelers at that time. Get yourself onto the waitlist now.

Include in your calendar both a “vacation” trip and a “travel” trip.

Trip sellers use the words “vacation” and “travel” interchangeably, but they are actually very different. “Vacation” is the opposite of work, whereas “travel” comes from the French “travail”—meaning, work. It is indeed a lot of work to cope with unfamiliar languages, currencies, etiquette, logistics, flight cancellations, lost luggage, etc. Each year we all need a good dose of both vacation (recovery from work) and travel (exploration that may tax the mind but also broadens it).  If what you really want is both in one trip—exploration with all the hassles removed—then use a WOW List trip planner.

Include in your calendar a new destination you’ve never been to before.

We all need the comfort of the familiar (e.g., the annual family trip to the lake), but we also crave novelty and excitement. Getting slightly out of your comfort zone leaves you with a sense of accomplishment, not to mention unforgettable memories. I insist that my kids (now 16 and 17) get to at least one new country each year. (Usually we get to at least three or four.)  If life gets in the way and you can’t get to a new place in 2020, at least, when you’re in the old familiar place, try a new activity you’ve never done before.  Mastering a new challenge—say, zip-lining or learning to surf—makes a trip vividly memorable.


Be a smarter traveler: Read real travelers’ reviews of Wendy’s WOW List and use it to plan your next trip. You can also follow her on Facebook, Twitter @wendyperrin, and Instagram @wendyperrin, and sign up for her weekly newsletter to stay in the know.


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