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.

6 steps to the vacation of your dreams

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.




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!

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.

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.




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.)

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?

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!


12 thoughts on “6 Simple Questions to Plan the Vacation of Your Dreams”

  1. Your drawings are so freaking cute! Sorry had to be said.
    I want to plan a vacation soon and I had no idea where to start. This really helps!

  2. I’m one of those people who just drops everything and goes. And it almost never works out. But I’ll consider this. Thank you

    1. Thanks! I hope it helps – though don’t abandon the drop everything mentality completely – I find that admirable 🙂

  3. I think the hardest questions for me are the ones involving time and money! I never feel like I have enough time or money for vacation, but I think I just haven’t been savvy enough! Thanks for this great list of questions to consider next time I travel!

    xo, Taylor || The Millennial Sprinkle (thesprinkle.tayloramead.com)

    1. I agree – they are both so tricky. If you plan your trip far enough in advance to save some money, however, it makes things much easier. I’ll be posting money saving tips in the next few weeks to help bring down costs, too 🙂

  4. Love the tips to planning your vacation, for me the planning phase is often the best part (I love to plan!) I think the key for us is getting leave and budget, we try travel outside of peak season to make it more affordable!

    1. I LOVE the planning, too 🙂 And yes – traveling out of season is a wonderful tip. It can save big money.

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