Behind the Road Trip: Planning Tips

I’m currently 91 days into The 100 Adventures Project, which means I’m a little tired and just the tiniest bit sick of my car. The obvious solution? Plan a weeklong family road trip around the Pacific Northwest! That sounds ridiculous, but the funny thing about adventures is that they encourage more adventures. So, road trip planning is in full-swing over here. That means that in the evenings, instead of Nextflix, it’s making popcorn and Googling “cool stuff in Oregon.” At heart, I am not a planner. I’d rather wing it, but I don’t want to miss out on any great stuff, and so…I plan. It’s not the most epic part of the adventure, but it makes it all possible, so here is a tiny look into the thought process behind our big adventures. 

Vacation or Adventurecation? We’ve started branding our trips as one or the other. Deciding this in advance helps not only with planning, but with expectations. If everyone is geared up for a week on the beach, but then you end up spending all your time driving to destinations and exploring hard, you’re going to have some ticked-off campers. Conversely, if you’re expecting to explore a bunch, but you end up stuck inside a cabin for a week, that’s a bummer. We’ve finally learned to hammer this out in advance. Our upcoming Oregon trip, for example, will be an adventurecation. We’ve got a large territory to explore, so we are okay with the fact that we’ll be staying somewhere different almost every night, driving a ton, not sitting under a beach umbrella drinking mai tais (sad to say), and napping a lot when we get home. But, although we’ll push our limits while on the road, we’ve planned it such that we will get back into town on a Friday and have a weekend at home to recover. 

Build in rest time. Especially if you picked option B, adventurecation, planned down time is critical. This is not my strong suit. When we’re traveling, I like to cram in as many sights as possible; I hate to miss a single sunset, scenic vista, or local bakery. But I’ve learned that this usually results in mutiny, and although I don’t like to admit it, I also need chill time. Sam and Annie do well with unstructured time in nature, preferably near water that they can splash in, without having to be rushed on to the next activity. Jordan needs a few quiet mornings with a cup of coffee and a book. And I need to be able to sneak out by myself occasionally to climb rocks or take pictures. For this trip, we are also planning a few times where the four of us will split up: I’ll take Annie on a hike, for example, while Sam and Jordan explore together. 


Figure out your priorities. We have two major priorities when traveling all together: 1) good sleep, and 2) good scenery. At this point in life, with two tiny kids, we choose our accommodations based on places we think the kids will sleep well. Basically, that means we over-analyze pictures online to be sure there’s a place in the hotel room or Airbnb where the kids can sleep out of our line of sight! And, when possible, we try to plan at least two consecutive nights in the same place. Also, this is kind of weird, but I actually try to find lodging near the best spots to photograph sunrise, so I can sneak out by myself early in the morning. All that to say: everyone’s got different priorities when traveling, and it helps to figure them out in advance.

Bring the right gear. I’ve got four words for you: suction cup blackout curtains (the single greatest secret to good sleep while traveling! That, and a travel sound machine for white noise). Seriously, though, we spend about as much time planning gear as we do planning itineraries. If we’re going be far away from amenities, we bring a huge cooler and a 7 gallon water dispenser, and we always pack for coffee self-sufficiency (that is, the ability to make coffee anytime, anywhere!). On this trip, we’ll be hiking in creeks and exploring beaches, which means a week of disgusting-clothes-purgatory, so I’m stocking up on gear that can be easily rinsed–lots of rash guards, hiking sandals, and plastic grocery bags. For the car, I’ve got stacks of flap books for Annie (Roger Priddy and Spot books are brilliant!) and lots of paperbacks for Sam (he is currently obsessed with Frog and Toad). We’ve also got audiobooks, podcasts, and an iPad full of Mr. Rogers episodes and calming Spot cartoons for the really long stretches of road. Also, a headphone splitter, so Jordan and I can hide out and watch movies in the evenings. Also, a stash of adult beverages for said evenings.

Research good spots. People ask me all the time how I find cool places to explore, stay, and eat. The sad truth is, I spend a great deal of my free time Googling “cool places.” I have an embarrassing number of notes on my phone and photos saved to Collections in Instagram. You’d be amazed at the results of a few carefully-worded Google searches! Using a lot of superlatives and specifics tends to yield good results. For example: “most scenic spots Oregon Coast,” “best Mexican food near me,” “hidden gems San Francisco,” “best things to eat in Oregon,” or “one day in Portland.” And, of course, there’s always Yelp, and asking locals for advice! 

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Make a Google Map. Living in Silicon Valley has taught me well. I now make a color-coded Google map for every single trip, adding hikes, scenic spots, parks, restaurants, and coffee shops, and consult it along the way. Whoever invented the “My Maps” feature…I should buy them a drink.  

Prep expectations. We talk about the plan for weeks in advance. For Sam, who, at 4 years old, is very structured and prone to anxiety, this is really important. For this trip to Oregon, we’re actually making him an itinerary booklet! It will include pictures of places we’re staying, friends we’ll see, and major sights, while also leaving lots of room for flexibility in each day. That way, he’ll have a sense of context and familiarity when we arrive at each place. Even Annie, who is 18 months, does well when she has the plan throughly explained in advance (“We are going to wake you up early and drive all day,” or, “Annie! You get to sleep under a hotel desk tonight!”). Despite our best efforts at planning, though, we can always expect surprises along the way…and that’s what makes it an adventure. 

I’ll be back in a few weeks with a report on this particular adventurecation and a full report on The 100 Adventures Project! 

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