After 2018’s road trip, we decided that we liked the travel format of visiting more places rather than just visiting one place during our trips. (More travel, less vacation.) The problem we still have is time. Our schedules only allow for a one week family trip during the year. We also have an annual travel budget to adhere to, so planning a trip for a family of four can be quite time consuming. We have found the best way to plan our trips each year is to plan in stages.
As you read in my Travel Budget post, I start planning our week long family vacation for the year first. It is our #1 travel priority each year. I start by getting as much feedback from my family on where they want to go and what they want to do or see there. I write down all activities they want to do such as horseback riding, kayaking, hiking, biking, sight seeing, a candy store, ziplining, magic show, concert, baseball game, etc. I like the kids and Ryan to pick something new to try each trip to help keep our adventures exciting and give them something to look forward to! After all of our ideas are down on paper, we pick our favorite destinations and activities, and then I figure out what will work best with our budget for the year.

Next, we figure out what date range that works best for us, (i.e. a two week span that works for us to plan within). Using a date range helps me when planning, because I can normally find airfare at a lower cost if we travel on certain days of the week. Transportation is the first thing I research and book for our trips. I figure out what types of transportation we will need for our trip (i.e. airfare, rental car, subway fare, etc.), write down the information I will need to get an accurate estimate on cost (i.e. number of people, date range, number of bags, etc.), then start my search for the best flight(s) at the lowest cost, because it tends to be the largest of our travel expenses. Once I have our flights booked, I book our rental car if needed.
When planning our lodging, I write down where we plan to be and when. If we are road tripping to multiple destinations, I try to look for affordable lodging within a certain radius. We have been able to save significantly on hotel costs by doing this. For example, we recently visited a National Park. The town located directly south of the park would be the ideal place to stay, but was quite pricey. Instead of staying there, we drove 20 minutes past that town to another small town where I was able to find a hotel room for half the cost.
When I have transportation and lodging booked, I start a rough itinerary as a guide for planning activities/entertainment and meals. It helps give us an idea of where we are going, what we plan to do there, and additional activity ideas for each location. We have found it helps to have a flexible plan for each day, so we can spend more time on the activities we are enjoying. The additional activity ideas help us in being prepared for unexpected cancellations, bad weather, etc. I also like to make sure I have dining options for our location(s). My family tends to function better when properly fueled for activities, so I like to keep their bellies full and happy!
If you have any planning tips you would like to share, please comment below. We would love to hear them!