
Jesse and I are heading off on a weeklong road trip in September. We are heading up to the Apostle Islands for a few days then heading across the UP of Michigan to Mackinac Island for a couple of days before heading home.
It has been a while since we have headed out on a road trip and we are pumped. And since I am a planner by nature and I tend to err on the side of over-preparedness, I am already deep into the planning of this trip.
I am going to walk you through how I plan our road trips just enough to satisfy my need for preparation without having a strict agenda. These steps, along with my tips for simplifying summer travel, will help de-stress getting out on the open road.
Step 1: PreTrip Planning
After last year’s Maine trip left us stuck at the airport for hours on end (canceled flights because of storms) Jesse requested this year we stick closer to home. We had been meaning to check out Mackinac for years, and Apostle Islands while not a National Park is part of the National Park system so we had to check it out.
After a bit of searching, I found and booked places on Airbnb. Airbnb, VRBO, and HomeAway have been our go-to for vacations for years. We have a much more relaxed experience when staying in a rental property. And let’s be honest – hotels are the worst.
If you are interested in trying out a rental for the first time, click through this link for Airbnb and get $40 off your first booking.
Step 2: Three to Four Weeks Out
As vacation time moves closer I start to a bit more research on the destination (or in the case of our upcoming trip – destinations). What touristy things to we want to do? Are there any fun restaurants/breweries/wineries that we want to check out? How about parks, hiking trails, museums, historical sites?
Yes, we are super nerdy.
I use Google Trips to keep everything all sorted and saved. I create a trip for each vacation (if you have flights and other reservations and use Gmail, Google will generate the trip for you). The app uses the power of Google Maps to help you find things to do, restaurants, and even collects discounts for you.
Step 3: Two Weeks Out
Now is a great time to get the car ready. Jesse takes it up to our mechanic, gets the oil changed, and has them check everything out. I also take this time to make sure we have all of the travel toiletries and clothing that we need for the trip.
We usually don’t end up buying much, but someone always needs a couple more pairs of socks, new walking shoes, or a hoodie that doesn’t make you look like a dirty hobo.
If I haven’t done so already I make a reservation to board our dog. I found a great place a few years back and Dru loves it. Seriously, he leaps out of the car when we get there.

Step 4: One Week Out
This is where shit starts to get real.
First up, I confirm our rentals and finish payments if necessary. I check the weather for the time of our trip and finalize our packing lists. We both have a pretty minimal wardrobe, so I need to do a final load of laundry and finish packing the night before we leave.
Since we are driving this time around, I will detail the car and pack it with its own unique set of road trip essentials. Here is that list:
Packing List for the Car
- Road Kit
- First Aid Kit
- A gallon of water
- sunglasses
- travel water bottles and coffee cups
- wet-wipes
- paper maps
- change and small bills cash for tolls/parking meters
- umbrella
- little cooler
- depending on where we are going I might throw in boots, heavy socks, coats, and heavy sweatshirts
Last, but most importantly, I plan out our road trip snacks and any other food we are going to bring. You can’t head out on the road without snacks, so that is a given. Sometimes we also bring along our own food to make at the rental. This is usually something easy like the ingredients for a quick pasta and stuff for breakfast.
Step 5: The Day (or Two) Before
Today is the day where all my pre-planning shines. I usually have a few loads of laundry to do (so we can finish packing), and I also clean up the house as much as I can.
Coming back to a clean home is the absolute best.
I like to take a few minutes to sit down and make a list of things I need to do in the morning, and then I try to relax.
Step 6: Go Day!
We (mostly me) are early risers, so we are up are ready to go early. We shower and dress while the coffee is brewing, the last few items are packed (mainly Jesse’s CPAP machine) we load up the car with our bags and snacks and head out the door.

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