Your Travel Cheat Sheet, Part 1
When to plan, when to book, and why it matters.
You know where you want to go. Now let’s talk timing. The earlier you plan with a travel advisor, the more choices you have—and that matters when it comes to the hotels, resorts, villas, ships, and private experiences that are best for you. But there’s no magic cutoff: Sometimes we can plan bucket-list trips closer to departure, but you’ll need to be more flexible. As WhirlAway Luxury Travel Advisor Jenny Seal puts it: “With trips this special, we want our clients to have a choice of everything that’s important rather than having to work around whatever remains available.” On that note, we’ve created this two-part insider guide to help you with the timing of busy seasons and traveling to the world’s most sought-after destinations.
Come back next week for our cheat sheet on the world's most coveted destinations, including Japan, Greece, Africa, and Antarctica.
LARGE GROUPS & MULTI-GENERATIONAL TRAVEL
Start Planning: These trips are extra-special, and timing always depends on where you’re hoping to travel, but with large groups, the who is equally important. Your group should first determine who is traveling and the dates that work for everyone. Without a defined date range, we can’t begin the planning process.
WhirlAway Tip: If you are coordinating several households, start the family conversation months earlier than you think you need to. Reach out to your advisor with agreed-upon dates or a narrow date range so the actual trip planning can begin efficiently.
WINTER HOLIDAYS
Start planning: Ideally 9 to 12 months out, but a minimum of 6 to 8 months.
Why timing makes a difference: The holidays are one of the busiest times of year to travel, and the best rooms, villas, flights, and special experiences go quickly. Prices are often double the average during these peak times, and many hotels have a minimum night-stay requirement—some resorts require 7 to 14 nights.
Family and multigenerational holiday trips require extra lead time because coordinating everyone’s schedules can be as challenging as finding the right accommodations. Finding the right room configuration and location can be just as important as finding the best hotel fit for your family.
WhirlAway Tip: If you’re able to travel just before or after winter break, pricing and availability tend to be much better. Start by getting the family committed to dates. You don’t need to know where you are going, but having everyone agree on when they can travel gives your advisor something concrete to work with.
SPRING BREAK TRIPS
Start planning: It depends on the destination, but typically, 6 to 9 months before travel. For seasonal destinations and experiences, like Japan’s cherry blossoms, planning should be done 10 to 12 months in advance.
Why timing makes a difference: Spring break creates a very concentrated period of demand, especially for warm-weather destinations and family-friendly resorts. While these breaks vary based on school schedules, they typically span the same three to four weeks. Because so many families are traveling during this time, the best rooms, convenient flights, and most desirable resorts can quickly become limited. This can leave you choosing from the very high or low ends of the spectrum, which means less desirable locations and rooms.
WhirlAway Tip: For families traveling with children, this is a great time to visit Europe to beat the summer heat. Use your vacations days before and/or after your spring break period to maximize the time you can travel. And if your kids’ break falls around Easter weekend, take the holiday or Good Friday school closures to shift your dates. Sometimes a little flexibility opens up significantly better options. Many schools allow up to five educational travel days, and what’s more educational than travel?
