Some choose to take the easy-going, meandering type approach, but in my experience- that is tough to do with kids. They want to know where we're going, and when, and what it will be like. There are few kids that I know that enjoy the unexpected. That being said, you could always save one of your stops as the "surprise" of the day.
Itinerary might be a strong word, and you might be picturing me marching my tribe through the streets at an exhausting pace- but that is not always the case (except, yes, in London- but in my defense- that might've been their one shot at seeing London). In my opinion, it’s always good to have at least a loose plan- so that A) you don’t miss the main sites and B) you’re not jetting back and forth from one end of town to the other- wasting precious sight-seeing time.
I usually loosely plan our itineraries based on “days” that can be moved around to fit the weather, our mood, kid melt-downs, etc. I usually try to put a “museum-ish” day between action packed adventure days so that it’s more low-key and the kids don’t get over-tired OR over-bored. For this, I use a website/app called- www.tripit.com. TripIt allows you to add in your rental confirmations, etc- if you choose, but I just mainly use it to “map” our sights. If you’re heading to a city you haven’t explored before- this is great to get your bearings and make getting around easy once you’re at your destination. I made sure to copy and paste lots of info on pricing, hours, etc. into the notes on the app, so that I wouldn't have to keep burning data when we were out sight-seeing. Here's a copy of the rough itinerary for Colorado Springs/Divide, CO.
Again, check Trip Advisor for reviews of destinations and things to do, and Googling the city will lead you to the city’s/chamber of commerce’s website, and you can check the community calendars to see what’s coming up. Many smaller towns have free events and festivals to show off local color, and I always check those for freebies. For instance, when I googled Colorado Springs, I found a free visitor’s guide I could order, a community calendar, as well as a listing of free museums, etc. that were low cost/free. You can visit their tourist website here. Some of these things are lesser-known gems- one being the Colorado Springs Pioneer Museum, which my older boys were surprised to admit- they enjoyed.
Once you've created a loose itinerary, if you are traveling internationally, or where cell/internet service will be a potential problem, then I recommend printing or writing these things down along with addresses, hours of operation and prices. This was extremely helpful in London, where wi-fi was not always easily accessible. You can do this, by clicking on the "print Itinerary" icon in TripIt, and then selecting print, or print to pdf for a nice, clean copy.
Don't feel chained to your itinerary! For example, the first day, we decided to skip the Air Force Museum and added in the local Airplane restaurant (mediocre food, but a must-do for aviation fans). We also had to book an appointment for the Wolf and Wildlife Center, so we ended up moving that to another day. The point of this Itinerary is not to make this regimented, but rather, just having all the information you need in one place, at your fingertips, and having a plan that maximizes your site seeing time. We ended up switching out a few of these places in order to squeeze in local things we found on the fly, or to slide in more relaxing down time. Regardless, we always knew our options, and what it would take out of the budget.
We absolutely loved every minute of our Colorado trip, and yes, I would go again. I would chalk this vacation up to one of the most relaxing, and one of my very favorites, and I think that the good planning process involved definitely contributed to our great experience. Do you have places you love to visit in Colorado? I would love to hear about them!