6 Simple Questions to Plan the Vacation of Your Dreams

As I mentioned in Monday’s post, Ryan and I are at Cape Cod this week, and we’re having a great time.  Perhaps not surprisingly, I have vacation on the mind, so I thought I’d focus today’s post on that. And more specifically, how to plan a successful vacation.



With just six simple – yet critical – questions to consider, you can plan the vacation of your dreams.

I'm Busy Being Awesome" quote, dreaming big, making plans, reaching goals.

Now you might think the first question to consider is: “Where do I want to go?” Surprise! That’s not it. (That doesn’t come until question six!) Rather, the first thing you should ask yourself is, “How much time do I have?” Are you looking to spend a long weekend? One week? A month? Deciding upon the length of your trip has a major impact on where you can go and what you can do – if you only have four days, you’re not going want to spend two of them traveling to some faraway destination half way around the world.

I'm Busy Being Awesome" quote, dreaming big, making plans, reaching goals.


Second, ask yourself, “What kind of vacation am I looking for?” Do you want a relaxing getaway? Are you looking for an active adventure? Maybe a little of both? If you’re a person who can’t sit still for more than 10 minutes, a relaxing beach getaway might not be for you. You’d be bored out of your mind within the first hour of your trip!

I'm Busy Being Awesome" quote, dreaming big, making plans, reaching goals.

Then expand this idea for question three, and ask yourself, “What specifically do I want to do on this vacation“? Are you looking for rigorous hikes in the woods? Do you want to spend hours wandering museums? Do you plan to fill your agenda with long days on the beach drinking margaritas? There are so many different types of vacations, and it’s very important to know what you’re looking for.

I'm Busy Being Awesome" quote, dreaming big, making plans, reaching goals.

Fourth, ask yourself “Who is going on this vacation?” Is it a solo adventure? Are you traveling with your fiancé? Are you taking all three of your children under the age of five? If it’s the latter… I’m willing to bet you’re not going to take that long trek through the mountains of Tibet. Make sure you know your travel companions – you want everyone on board with the vacation, or Debbie downer will be a bummer for everyone.

I'm Busy Being Awesome" quote, dreaming big, making plans, reaching goals.


Fifth, ask yourself “How much money do I have to spend?” This is a critical question. You can spend big bucks on your travels, or you can be rather frugal, and a lot of this depends on where you travel, what type activities you do, whether you plan to eat out each meal, and what time of year you’re taking your vacation. (If you are traveling to Disney World during spring break, you’re going to pay a premium compared to traveling to Disney in the peak of summer.)

I'm Busy Being Awesome" quote, dreaming big, making plans, reaching goals.

So now that you know how much time you have, what type of vacation you’re looking for, what you would like to do, who is going, and how much money you have to spend, now you can finally ask yourself: “Where do I want to go?”The previous five steps will help ensure that you choose the best destination for your time frame, your budget, your fellow travelers, and your ideal activities. Simple, right?

I'm Busy Being Awesome" quote, dreaming big, making plans, reaching goals.

What do you take into consideration when planning a vacation? Do you have any upcoming plans this summer? What is your favorite time of year to travel? Let me know below!


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