Six Must-Ask Vacation Planning Questions

If you’ve made vacation arrangements of any kind, you’ve probably been there: staring at a computer screen with what seems like 11 billion choices staring back. Analysis paralysis kicks in; there are so many options, it’s overwhelming!

Though it may seem impossible to wade through all the options, there are easy ways to focus your thinking and choices. Employing a little strategy is essential to breaking through the wall of options and zeroing in on the best choice for a particular trip.

Here are six questions to help focus your search and maximize the value of your next epic getaway:

Where do I want to go on this vacation, and when?

This seems like an obvious question on the surface, but it is an easy source of both confusion and clarity. A quick check of weather patterns and temperatures can ensure an ideal trip timing for your preferences.

Some people think about the Bahamas in January or South Africa in July, but those locations are cool to cold at those respective times of year. The Caribbean is almost always warm, but a trip in February is very different than a trip in August — the heart of hurricane season. Rainy and dry seasons, and warm and cold seasons, vary by location and time of year. The bottom line is that knowing what to expect, and ensuring it matches your expectations, is key.

Does the amount of time I can be away correspond with the type of trip I want to take?

Even for experienced travelers, there’s a point of diminishing returns in a jam-packed itinerary. There’s a sweet spot where you can feel like you’ve done plenty without feeling like you’ve missed out.

If you’re planning a two-week European vacation, for example, the rule of thumb is at most three nearby cities (for example, London, Paris and Amsterdam) as a base. If you can only get away for a week, first consider a closer destination, then one to two locations from which to operate. You can immerse yourself in the local scene with plenty to see and do, without breaking your neck to shoehorn your entire bucket list into a timeframe that just won’t fit.

What kind of vacations do I typically enjoy?

Evaluating how you tend to approach vacations is an important question that doesn’t always get framed this way. You may know that you’re a total beach person, and that you could do the beach and pool for a week at an all-inclusive and be completely content because all you want to do is relax. A lot of go-and-do might not be your idea of a good time.

For the go-and-do person, though, more than a couple of days of just hanging out by the water may leave you stir-crazy. Maybe you’re in between somewhere, in which case you could go either way.

Even if it seems like a good idea at the time, evaluating your approach to vacation is a valuable tool in planning the right trip for your personality. This will also inform your level of planning, the types of activities and excursions you want to pursue, and other key components of your vacation.

How much do I care about my accommodations?

This is not recommending bottom-of-the-barrel properties, nor insisting on the Four Seasons. Your views on accommodation, however, will go a long way toward maximizing your vacation experience. There are budget considerations, of course, but you should consider your preferences and purposes.

Do you simply need the bells and whistles of a higher-end hotel? Is your hotel room a sanctuary after a long day or a place to crash between adventures? Do you need a hotel near a specific location (for example, the Acropolis in Athens), or is near public transport acceptable? Do you require a hotel, or is a rental home or villa OK? These questions help narrow down options that appeal to your needs and wants.

Am I OK traveling on my own or in my own party, or would I feel more comfortable going with a group?

This answer shapes the type of vacation experience you’re going to have. Many folks are used to DIY-ing everything these days, and that can include travel. For those folks, either a fully customized travel experience or a short-burst small-group activity would be best (for the record, this is my preferred method of travel).

For first-time travelers, or folks who are traveling by themselves but don’t have the full independent spirit, there are plenty of options that can put your mind at ease. Whether joining a fully escorted tour, adding in small- or large-group excursions from day to day, or booking into an affinity group on your cruise or land holiday (travel agencies occasionally have existing groups you can join), there are plenty of options to help you feel right at home away from home.

What’s the best way for me to plan this vacation?

Experienced travelers might be savvy enough to navigate through the options online. But if you don’t have the time, energy, confidence, experience or desire to cut through the legwork that planning that amazing vacation will entail, there are experienced travel professionals who will use their knowledge and connections to design the perfect vacation built specifically for you.

There are plenty of things to consider when planning an upcoming vacation, but these simple questions will put you well on your way to crafting a truly epic journey.

In addition to covering high school sports for the Severna Park Voice, David Bashore is a travel agency owner with more than seven years of experience. He has sent thousands of people to more than 150 countries across six continents. He can be reached at info@fairwindstravelagency.com.