1) Pick somewhere that inspires you.

2) Go.

In all seriousness, this is how my wonderful husband travels. I usually initiate any serious conversation about a place we have often thought about going to “one day”. We pick a place. He tells me what t-shirts he wants to take and then all of the sudden I am telling him which carry-on he is responsible for getting through security and where the items are that he has to screen separately.

For me, the process is much more involved.

  1. Decide where to go. Pick a bucket list place, a bing background, somewhere significant or the birthplace of your favorite food. Near or far, go!
  2. Figure out when you want to be there. Do you want to be there for a special event? The quietest part of the year? The cheapest? The driest? The warmest?
  3. Decide where you are fixed and where you are flexible. Flexibility means more options and more options usually equals cheaper options. You may be flexible in when you go or how long you stay, but not where you stay or visa versa. You might absolutely want to drive yourself, or not. You might can stay a day longer or may leave early.
  4. Figure out how you will get there. Do you need the flexibility of a car? Will you fly? Are there train or bus options? Can you get there via cruise?Are you wanting comfort and leisure? Speed? Cheap?
  5. Prioritize. Is budget friendly the most important? Is relaxing? Is seeing as much as you can see? Decide ahead of time what is most important to get out of your trip.
  6. Plan your “must do’s”. Make sure you don’t miss the most important things to you and know what parts of your trip are non-negotiable. This helps you avoid post trip regret.
  7. But leave enough room for surprises. Some if the best experiences are spur of the moment and done on a whim!
  8. Group the things you plan on doing geographically. On a whirlwind trip to NYC, we had barely 36 hours. Planning our activities by section of Manhattan allowed us to do far more than we thought possible. Getting there may be half the journey, but it saves time if you can go in circle and avoid backtracking.
  9. Hotel location is critical. If budget is the most important thing to you, plan to stay farther away from the action. If time is most important, pick one in the heart of all. If you plan on taking public transportation, make sure you are close enough to a stop to walk back and forth. If you are setting up a base camp you will need a different type of hotel than if you just need a place to get a shower and a good night’s sleep.
  10. Don’t forget to enjoy yourself. Soak it all in and don’t be so focused on your plan than you forget to live in the moment.

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