This may seem like a no brainer, but when you have this magnificent idea of going to Hawaii when your budget will allow for a long weekend in Chicago, then you have some rethinking to do. Do you need that vacation soon or can you wait to save up money for that Hawaii trip? Also, as much as traveling is fun, there is no reason to go into debt for it. It will stress you out in the long run.

Whoever you are going with has ideas and hopes of their own for the trip. Let them contribute to planning! Everyone will be happy and parts of the trip will be a surprise for you too.

Keeping this in mind will help you decide what you actually can do on the trip. It will help you prioritize activities and sites as well as give you an idea of how much downtime you will have (unless your whole vacation will be downtime). It can also help with the budget, especially if you have to figure things in like child or pet care.

Another duh, but a really important one. Especially if you are traveling overseas. There may cultural considerations to learn about, power adapter or converters to be purchased and documents to gather and share with people you trust. It will also help you figure out if you need to make any purchases for the trip, like insect repellent wipes.

I sometimes find myself wanting to plan the perfect vacations since we have these limited pockets of time to travel and I don't want anything to go wrong. But the more I let go, the more I actually get to enjoy myself in the planning process and get excited about the trip. Leave some things unplanned. Go with the flow. It's OK. Uncertainty can be exciting and awesome. So go ahead and kick your inner Danny Tanner to the curb and just have fun.