January is a great time to grab a calendar, look at the year ahead, and plot out where in the world it might take you.  First, planning out your vacation days in advance helps ensure you don’t lose that workplace benefit.  Second, it enables you to 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. Third, it gives you something to look forward to throughout the year.  So, each January, I sit down with a calendar and approach my vacation planning the same way I approach my household budget planning, so as to maximize my travel dollar, time, and enjoyment.  Here’s how I do it:

Grab your calendar and look at when the school breaks and 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. (While you’re checking your and your family’s work and school schedules, also check everyone’s passport expiration dates. If anyone’s passport is expiring this year or early next, read this.)

Predict what weather-related escapes you will need when.

I know, for instance, that when February 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 loved 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).

Know 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 will give you plenty of shoulder-season ideas for those windows of time when you have availability.  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. Here are smart shoulder-season options for spring break 2024.

Consider where your money will stretch furthest internationally.

It’s smart to factor exchange rates into your decisions. Central America is always one of the most affordable regions in the world.  Read these Belize, Costa Rica, and Panama trip reviews to gain an understanding of what a fun and authentic tropical vacation you can get at a better value than on many Caribbean islands. At the other extreme, Japan and Scandinavia are always among the world’s most expensive countries, as are France and Italy at the 5-star level.  Airline routes and fares also determine trip cost and convenience, of course.  Check out Nonstop Flights To Make Your Travels Easier.

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 (Google Flights, Kayak, Hopper, SkyScanner) that will send you notifications when fares drop on specific routes or specific dates or both.  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.

Especially if you’re Europe-bound, book early.

Italy, France, Greece and other Mediterranean and Western European countries have been extremely popular in the wake of the pandemic, and with all the events coming to Europe this summer—from the Paris Olympics to Taylor Swift concerts—airfare is not the only component of your trip that should be booked well in advance. Say you want to go to the Netherlands to see the legendary springtime tulips—and, while you’re in Amsterdam, visiting the Anne Frank House is a must. Tickets for that become available six weeks ahead and sell out quickly. If you figure out your Netherlands dates in January, you can snap up tickets to the Anne Frank House and Keukenhof Gardens as soon as they are available.

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 an excellent destination specialist who knows all the insider tips and tricks in the place where you’re headed. How do you find the best specialists around the world? Use our WOW List of Trusted Travel Experts as your first resource. Click the button below to get started:

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

If you think you might need a room at a popular resort, reserve your spot, as long as you can do so with no cancellation penalty. The more in-demand your destination and timing, the harder this will be.  Islands in particular have limited flights and limited hotel options, leading to high prices and cancellation penalties. 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, ask 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.

It is easier and likely more effective, of course, to contact the right destination specialist and have them work their magic via their local hotel connections.  But destination specialists typically won’t book hotels only, so contact them only if you plan to book local activities and experiences through them as well.

Start thinking about Christmas/New Year’s now.

I’m not kidding. Get ideas from these Christmas/New Year’s trips most loved by your fellow travelers.  If you need a beach or ski resort, remember that you’ll find peak prices and minimum-stay restrictions at this time of year. Some of Hawaii’s top resorts, for example, are already fully booked for the December 2024 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—then a few rooms may open up to new travelers at that time. Get yourself onto the waitlist now.

Include in your 2024 calendar both a “vacation” trip and a “travel” trip.

Trip sellers use the words “vacation” and “travel” interchangeably, but they are actually very different.  “Travel” comes from the French “travail” (meaning, work)—and it is indeed a lot of work to cope with unfamiliar languages, customs, currencies, etiquette, logistics—but it expands one’s mind and horizons.  By contrast, “vacation” is the opposite of work (in fact, it’s recovery from work). Each year we all need a good dose of both vacation and travel.  If what you really want is both in one trip—exploration that’s as relaxing as possible, with all the hassles removed!—that’s when to use a WOW List trip-planning expert.

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 get to at least one new country each year.  If life gets in the way and you can’t get to a new place in 2024, at least, when you’re in the old familiar place, try a new activity you’ve never done before.  Mastering a new challenge—say, learning to surf or cook the perfect tiramisu—makes a trip vividly memorable.

Need help perfecting your 2024 travel calendar? We can help if you click the button below and tell us what you’re seeking:

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