20 Questions to Help Choose Your Vacation Destination

Unless you’ve always dreamed of going to a certain place, picking where you want to go for your next trip or vacation can be a little daunting. The world is such a big place! How do you choose with all of the options out there? Here are a couple questions to ask yourself (or someone else) to narrow down the options.

  1. What kind of weather do you want? Do you prefer somewhere hot and sunny, cold and snuggly, or somewhere right in between?
  2. Can you afford traveling in peak season, or do you need to look at shoulder/off season destinations?
  3. Are you willing to take a plane?
  4. How long are you willing to sit in a car, or a plane, or a bus? In other words, what is your max travel time? If you take the number of hours it will take you to get to your destination and divide it by the number of hours you will spend actually on your trip you will get the percentage of your trip that is travel time.
  5. Are you willing to go somewhere that’s hard to get to? For example, there are some places where you have to take a plane, drive a few hours to get another plane and then take a ferry to get to.
  6. What is the biggest time difference you’re willing to travel? Will jet lag take away from your vacation/trip time?
  7. Do you want an all-inclusive trip?
  8. Is there an event (food festival, concert, speech, conference, rally, sporting event etc…) rather than a location that you really want to attend? Think about your passions, hobbies and interests to come up with ideas.
  9. Is budget an issue? Where are the best flight deals? Try using the ‘everywhere’ feature on Skyscanner to get an idea.
  10. Do you want to go somewhere that requires a Visa or entry fee?
  11. Are you okay with going to a place where you don’t know the local language?
  12. Do you want to go somewhere with an unfavorable conversion rate? Or maybe a somewhere with a very favorable conversion rate? Or maybe it doesn’t matter at all.
  13. Do you have someone traveling with you that will require special needs or special activities? Do you need somewhere that is wheel chair accessible, or a place with a variety of things to do for kids, or a place with easy transportation for those who can’t walk long distances.
  14. Are you willing to get vaccines that some countries require? Do you have enough time to get them if you are willing?
  15. Do you want to be in a secluded area or a big city/tourist area?
  16. Are you okay with being in a place that doesn’t take credit card?
  17. What would you like to experience for this trip? Relaxation on a beach? Culture and museums? Adventure and hiking? Sipping wine in the countryside? Cruising on the ocean?
  18. Do you want to plan the trip yourself, or have someone do it for you?
  19. Would you prefer fine dining locations, casual fare, or somewhere that just has a lot of options?
  20. Do you have a list of places that you’ve always wanted to go to? How do those line up with the way you answered the other questions on this list?

Once you’ve asked yourself some of these questions, you will have narrowed down your choices quite a bit. Now you can start to look in books, talk with family and friends, and search online and through social media for inspiration. Some of my favorite places to look are Pinterest, Instagram, Guide Books on a certain region, and travel blogs.

Once you have a couple of options, go back through your list of wants and see which one is a better fit. If all the choices seem equal, which destination do you feel most comfortable or safe traveling to? Which location will be more financially feasible? Is there one that is just calling your name, but you can’t pin point why? Go with your gut!

Once you have decided on a place, it’s time to start budgeting and planning, but the most important thing to do is just BOOK THE TRIP! In life I think you come to regret the things you didn’t do more than the things you did. I have somehow managed to have the best trips in the places where the most things went wrong, so don’t let the little voice in the back of your head steer you away from an amazing adventure.

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