I am planning trips constantly. If there isn’t one in the near future, I plan what I want our next trip to be.

Here are my first three initial questions when planning a trip:

  1. Where are we going?
    • Do you have a specific country or city? Maybe a continent? Start big and dream big!
  2. How long will this trip be?
    • Do you have a summer off, a week or two maybe? This will help you be more realistic with your itinerary.
  3. How much will airfare cost?
    • This helps with budgeting. I started here and used skyscanner to find the cheapest place I could fly to during Thanksgiving break, I had nine days and wanted to go somewhere, but didn’t have a lot saved up. Costa Rica ended up being the cheapest to fly to from Texas. I then used Google Flights to pin down the days I would fly.

Once I have these three steps conquered I can begin the next phase of initial trip planning.

  1. How much will accommodations be?
    • I start with having two tabs open on my computer, Airbnb and booking.com. For me with accommodation; safety, free wifi, and price are my top priorities
  2. What do we want to do/what are the costs of our activities?
    • This is more to help with how long we want to stay in a city than budget. I always go to guide books and blogs. I don’t really find Trip Advisor useful for me, but lots of people do! I’ll spend a few hours on Pinterest and at Barnes and Noble.

Once I have a rough idea of my ideal trip planned I allow reality to set in. What is the length of time we actually want to spend in each city? How much can we save or have we saved?


Here is an example for our 8 week trip to Europe:

I knew that we wanted to go to Europe; it can be expensive to fly to, but relatively inexpensive to travel around. We decided 8 weeks was how long we were going to spend abroad. You can see how we found cheap airfare to Europe and around Europe here. If you want to check out how to fly budget airlines and LOVE them, you can see that here.

Initially we were going to go to Spain, Italy, England, Netherlands, Denmark, Portugal, Austria, Switzerland, Germany, France, Czech Republic, Poland, Ireland, Hungary, Romania. I know that this is a lot of countries; I was dreaming big.

  • Spain-10 days
  • Italy-12 days
  • England-2 days
  • Netherlands-2 days
  • Denmark-2 days
  • Portugal-3 days
  • Austria-2 days
  • Switzerland-4 days
  • France-7 days
  • Germany-6 days
  • Czech Republic-3 days
  • Poland-5 days
  • Ireland-2 days
  • Hungary-5 days
  • Romania-3 days

Bummer, we only had 56 days. After trimming some things we came to this itinerary:

  • Dublin-2 days(arrive and depart)
  • France-5 days
  • Poland-4 days
  • Czech Republic-4 days
  • Italy-11 days
  • Portugal-6 days
  • Spain-14 days
  • Germany-5 days
  • Budapest- 5 days

Removing countries or days was due to price or amount of time we wanted to spend in each place, I believe the longer you stay in one place the better. My initial plan was extremely ambitious and way more costly due to accommodation in some of the cities and cost to fly or ride between so many different places.


I hope this helps! How do you usually begin your trip planning?


23 thoughts on “3 Initial Questions to Ask When Planning a Trip

  1. As someone who has done a decent amount of traveling, I think this is a helpful list of questions. There are many things that I had to learn on my own through trial and error. I wish I would have seen such a list long before I first set foot on an international airplane. Great post!

  2. Your Europe itinerary sounds epic! I ask myself a similar list of questions when planning a trip – cleanliness and convenience are 2 additional major factors that I consider when I’m booking accommodation.

  3. The most strenuous part of the trip, Planning and budgeting! You have penned it down so smoothly and nicely! Loved it👍🏻Thanks for Sharinv your thoughts and for flight booking do check out “Momondo”

  4. I go about it more or less the same way. I usually look at how much time I can get away and then think: owh if I have 2 weeks I could go here and there. But last trip was just me looking at discounts and thinking: owh I could go there!! Lol

  5. My trip planing similar to yours. I start big but in the end arrive small lol. Always I underestimate days and budget, but anyway, it’s more fun this way :))

    1. I’m the same! So, now I try to have an extra day more than I think I need in each city and 20 percent of my anticipated budget as back up.

  6. Great tips 😀! Booking a holiday yourself can be tough so it is nice to have a list of resources like this. Thanks for sharing!

  7. I can identify myself a lot with this post. I´m also constantly planning trips. If I´m not planning my next one I´m dreaming about all the places I want to visit as soon as I have some free days 😉

  8. Planning a trip can be so overwhelming – especially you don’t travel frequently or are going somewhere totally new. Your itinerary for Europe sounds amazing too! It always feels like there is never enough time to see everything.

  9. Yay!! This is so timely, I’m currently drafting my euro trip and this is so helpful. Though I might just end up seeing a bit I don’t have that much time. Which city did you like the most? 🙂

    1. This is actually for this summer, but so far out of these my favorite is Sevilla, but I think my new favorite will be Munich.

  10. Great Eurotrip. We had to drive from Hungary all the way to Portugal so naturally we started creating a similar itinerary….but because we were due to leave for Japan for a whole month, we had to trim it down haha like…to 12 days or something.
    We are so going to drive through Europe again and again.

  11. It’s very easy to want to do too much but I find it’s too much stress to even be worthwhile. Glad you were able to make your itinerary work for you 🙂

  12. Excellent tips. We’re always the same with ambitious plans, but like you, we usually manage to come to our senses and cut it down before we actually get out there! After all, travel is about much more than just the time you spend on a bus or train 🙂

  13. I tend to always forget about Google flights. It’s such a useful tool! You did such a great job editing down your list of countries for your eight week trip! Well done!

  14. What a great way to plan for travelling! Too bad you missed out on Scandinavia though, I’d love to show you around some day 🙂

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