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How I Plan My Trips

How I Plan My Trips
How I Plan My Trips

One thing that I pride myself on is my ability to plan out vacations. This includes everything from where we’re going and how are we going to get there, to where we eat and what activities we do. Everyone is different and the most important thing is to make your vacation specific and perfect for you, it doesn’t matter what anyone else thinks as long as you have fun! We like to have everything planned out, to the minute, when we leave for a trip. Things can always change and we’re pretty flexible, but we like going in with a plan.

Granted, I’m also known to plan out my vacations so much that they become un-fun. So take everything I say with a grain of salt. At the end of the day, your personal preferences are what make your vacation great for you. Some people like to plan out their vacations on the plane or the day of to be more spontaneous. I even know people who don’t book their hotels until they get to their destination. This would drive me absolutely insane so it wouldn’t work for me.

  1. Pick a state/country to visit
    • Typically, this comes from my bucket list and cool locations that I’ve found on Instagram. Luckily, we’re fairly new to the world of travel so our current locations are not off-the-beaten path, they are standard tourist spots.
  2. Pinterst (and Instagram) said state/country to figure out what destinations or activities that you want to hit while you’re there.
    • The main thing I look for is incredible locations, views, and (of course) where to eat.
    • If you’re looking for good places to eat make sure to Yelp them first.
  3. Based on the activities, figure out what city you want to stay in.
    • Another good thing to check out is how long it’ll take to do each activity and how far away they are from each other.
    • Depending on how long you want to be there will depend on which activities you do.
  4. Decide what time of the year to go
    • This can be as simple as Googling, ‘best time of the year to go to xyz’. But you can also answer a couple questions about the city itself:
      • Is there a festival or event that you want to go to?
      • Are there certain seasons that place is known for, like fall or springtime?
      • Is it a popular tourist destination for summer or Spring Break?
    • Personally, I prefer to plan out my trips at least a year to ten months in advance. It seems crazy but this way I can figure out exactly what I want to do and have a full itinerary. But more importantly, I can figure out how many points I need and what credit cards I need to get in order to meet that goal.
  5. Head to Chase Ultimate Rewards websites to see what hotels you can use point on.
    • During this time I also research what credit cards I’ll need to get, in order to get the bonus points needed to pay for the trip, if I don’t have enough.
    • This becomes tricky because you might also have to ask yourself, am I willing to spend money instead of points?
      • For example, I’m trying to get to Bora Bora at least once in my life and through extensive research I’ve decided that there are too many hoops to jump through in order to use my hard earned points and I’ll most likely have to pay in cash for this trip. Which is fine, but it means I have to save up before I go and put this trip off until I’ve saved up enough money.
  6. Check flights and determine if you’ll be able to use points
    • I’ll be honest, sometimes it’s extremely hard to use points on flights. I always assume that I’ll have to pay out of pocket for a flight because I don’t want to be limited on when I can go or how many hops I have to make in order to use my points.
  7. Book trip
    • Typically, I don’t book a trip until about five to six months out. Mainly because I don’t like to request time off from work until it gets a little bit closer. It also allows you to be a little more flexible.
    • But I have everything planned out so that the second I go to book a trip, I know exactly what I’m doing and how many points and dollars it’ll cost to get us there.