Pre-Travel Planning and Staying Organized During Vacation

I'm busy planning our next epic trip, a 6-state summer adventure, anchored by a friend's wedding in Ohio. I thought I'd share with you everything that goes into planning a deRosier multi-state trip, packed with as many attractions and as much learning as we can squeeze in. This type of travel isn't for everyone, but we're big fans of thoroughly experiencing a place when we visit and not wasting a minute. We want to visit the most important historical sites, try the local food, enjoy the natural environment, view the local art, and revel in what is different about the location from where we live. 

The trips vary a little bit, but the main steps I go through for a major, multi-destination trip are:

  1. Pick primary destination
  2. Pick secondary destination(s)
  3. Set start and end dates for the trip
  4. Buy plane tickets
  5. Schedule bunnysitter
  6. Start travel binder
  7. Research attractions
  8. Read about quirky or unique things about the destinations
  9. Create calendar with rough plans penciled in
  10. Book hotels and rent car
  11. Contact media relations staff at museums, visitors' bureaus, etc. 
  12. Schedule any time-specific activities (tours, shows, etc)
  13. Fine-tune calendar with important activities blocked in
  14. Research restaurants and local specialties
  15. Print a daily schedule with all information in one place

It sounds like a lot of work... and it is! But I love every minute of it. By putting in so much work ahead of time, we are able to see and do so much more on the trip. Every minute of research I put in translates to understanding the destination better and thus making informed decisions about where to go in our limited time. We don't go home disappointed to have missed something that we didn't learn about until it was too late. 

Most of the steps are self-explanatory, but I to want do share more about my travel binder and the daily schedule that goes into it. This is what the first page from our fall trip to Maryland, Delaware, Pennsylvania, and New Jersey looked like: 

Here's the same page with arrows pointing to the types of information I include on each page.

I create a page like this for each day of the trip, slide them into page protectors, and put them in a 3-ring binder. Here's that same Annapolis page, Day 1 of our trip, in the binder. I use the pocket on the left to hold tickets, brochures, maps, or other paperwork. This binder works really well for me and keeps me organized both in the planning stages and while we're traveling. 

All the information for Annapolis fit on a single page. When I need more than one page for a day, which sometimes happens when there's no particular order of how we need to schedule things over the course of two days, I just use two page protectors. These pages are from our time in Baltimore

Are you a very scheduled traveler like I am, do you plan nothing and go with the flow, or do you fall somewhere in between? I'd love to hear from you!


  1. I knew I loved you!!!! I do the SAME THING!!!! Mine is in a pocket folder, but same concept! LOL!! :)

    1. I'm not surprised to hear you do this! LOL! I use a pocket folder for short trips and the 3-ring with page protectors for trips that are 2+ weeks with a lot of different destinations.

  2. This is the perfect post - John won a trip to Bermuda through his work, and we are leaving next Sunday!!!! I will definitely follow your advise! There's so much to do and see there and so little time!


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