How To Plan A Vacation Using the 5Ws (and 1H)

In childhood, we learn about the key questions to ask to understand a situation. Who, What, When, Where, Why (and How) can be used in any circumstances, even when figuring out how to plan a vacation.
So let’s walk through a few questions to help you start with your process of planning a vacation:

WHO are you planning a vacation with?

Do you want to fly solo or travel with a group? Will it be you and your family (including grandparents) or your best friend from college? Answering these questions may mean the difference between a wild weekend in Las Vegas or a family trip to Orlando.

WHAT activities do you want to do?

Different people have different travel styles. While one person may be happy sitting by a hotel pool all day, another person may want to explore all of the areas historical sites or art museums, and someone else may want to discover the natural area nearby. When planning a vacation, take the time to understand what types of activities you and your traveling companions are interested in. This helps to develop an itinerary that works for everyone.

WHEN will you be traveling?

When do you plan on taking your vacation?  What season will it be? Do you need to anticipate weather-related problems like a snow storm in the winter or a hurricane in the summer or fall? Is it high-season in your destination? Will it be so crowded you’ll need to plan additional time for some activities? Or will you breeze through lines because no one else is there during the off season?

WHERE will you be traveling?

Do you want to stay close to home for a short weekend trip? Or will you be going around the world on a gap year? Are you heading some place warm like a beach or someplace cold with plenty of snow? Perhaps you’re dreaming of a tropical adventure vacation in the rainforests of Costa Rica. For many people, this may be the first question they ask when they start trip planning, but your answers to some of the other questions may guide you in deciding your destination. Don’t get stuck on a dream destination when there may be an alternative that’s similar (and possibly cheaper!)

WHY will you be traveling?

There are any number of reasons people travel: to take a relaxing vacation, to volunteer, to study a new culture, to transact new business. Or perhaps you’ve only traveled for vacation and may want to consider a different type of vacation, like voluntourism or ecotourism. Your inspiration for travel may give you any number of new experiences and memories.

HOW will you be traveling?

Have you ever considered that how you travel may just in and of itself be the reason for travel? People who cruise are familiar with this concept. But have you thought about taking a vacation by rail? Or maybe using your budget for a high-class, long-haul airline flight? Don’t limit the joys of travel to just your destination.

What Are Your Tips for How To Plan A Vacation?

Share them with us in the comments below! (And, regardless of how you plan your vacations, be sure to consider travel insurance from RoamRight!)

Note: Available plans and coverages may have changed since this blog was published.