Last winter my wife and I did the coolest, most random thing we’ve done as a couple yet when we took a road trip from Seattle, WA to San Francisco, CA over the course of 9 days. We ate amazing food, saw waterfalls, met overly friendly L.A. dudes, and enjoyed the kind of spontaneity that feels rare in my adulthood.

Personally, I think road trips are the absolute best form of travel and there is no shortage of great place to see. I would make a trip every year if I could.

Part of being a 20 something is finding ways to fit youthful spontaneity in our increasingly adult lives. Road trips do just that.

Here’s how we planned ours

Step 1: Pick a Time

In a perfect world this would be the last step, but it’s not a perfect world and unless you’re an heir to the Hilton fortune (looking at you Paris), this step must come first. A proper road trip takes several days—ideally a week or more. So the obvious hurdle is figuring out how to get out of work for that length of time and also coordinating with your travel partner (in my case, my wife) to make sure they can be away that long as well.

I guess my tip here is to try your best to work around times your work would already be slow or you’d be off anyways. My wife and I took our road trip over Christmas break last year because that’s the only time other than summer that schools shut down. Also, if you travel around Christmas, you can usually get several days (Christmas day, New Years Day) off automatically.

Step 2: Pick a Route

Unless you’ve done every classic American road trip, I don’t think there’s any need to reinvent the wheel in terms of picking where to go. There are so many amazing places to drive that it’s kind of absurd. A simple internet search should leave you inundated with natural beauty and overwhelmed by wanderlust. Whether you want mountains, desert, coastlines, or Kansas, there’s great stuff everywhere.

The Pacific Coast was so great because the entire drive was beautiful which is important when you spend a large portion of your vacation driving. Highways are way better than interstates for this kind of travel so definitely look for those.

My recommendation is you start by picking a part of the country you haven’t seen. We picked the Pacific Northwest because my wife had never been and it’s one of my favorite places. I spent a couple years in Oregon growing up and I’ve never been able to forget about it. In middle school, I was a weird annoying kid who talked about Oregon waterfalls too much. Just ask my friends–it was probably pretty weird to them. There’s also the Grand Canyon, Route 66, the East Coast, etc. Just use Google maps—there are too many cool places to list.

Need some inspiration?

Here ya go

Here ya go again

and again

I mean, look at this!! Finish reading this post, then start planning!

Step 3: Plan Your Stops

We learned that planning things to do ahead of time is important. Once we got on the road, it was harder to find cool places to visit or eat because honestly, we were tired. The more planning you do ahead of time, the easier it is to relax and enjoy it while on the road. Also, you can always change plans if need be. Book most of your hotels and any big attractions ahead of time if possible.

That said, it’s also very important that you plan for both rest and spontaneity.

We gave ourselves one day where we didn’t book the hotel ahead of time so we could decide to stay in upstate California or push through to get to San Francisco. We also took at least one day off in between all our driving days. Those were the times when we explored the cities (Seattle, Portland, San Francisco) and the surrounding areas. Don’t spend every day driving, this is very very important!

Obviously, you can do it however you want, but I think it’s important to make sure your road trip still feels like you have the freedom to change plans and you’re not totally exhausted every day. The whole point is to feel young and spontaneous–don’t become a slave to your schedule.

The tools I used to plan our stops:

  • Google Maps
  • Google Drive (to keep the itinerary)
  • Tripadvisor (great way to decide what to do in each place)

Step 4: Work the System to Save Money

The whole reason my wife and I decided to take our trip was because of the Southwest Rewards credit card. This isn’t an ad for the airline or card, but I honestly don’t think we would have done it without the points we got from signing up for this card. We used our 50,000 starting bonus points to book all our flights which was a great way to get ‘free’ transportation to Seattle and home from San Francisco.

The point is that there are hundreds (thousands probably) of rewards programs you can use to your advantage. We used a combination of, Airbnb, Kayak, and for our trip.

We started planning well in advance so we were able to build up our Southwest card purchases. If we would have been smarter, we would have put all our purchases on that credit card and earned enough points to also get some free hotel rooms or rental car days. Which reminds me…

Step 5: Make a Budget

No getting around it, road trips are expensive. My wife and I saved a bit every month to help prep for our trip. Then, like kids, we used our Christmas money on it. We started budgeting 6 months out which really helped the saving part. Also, booking things in advance helped us not think about money so much once we were actually on the trip. That’s nice too.

Step 6: Experience Everything

As Tom and Donna would say, Treat Yo Self! In our experience, the things we enjoyed the most typically weren’t that expensive, we tend to mostly like cheap things. That said, we did splurge on a couple things and  I think it was well worth it.

Expensive Things that Were Well Worth the Cash

  • One Night’s Stay at an amazing Bed and Breakfast in Northern California–more about this below.
  • The Exploratorium Museum in San Francisco–coolest place ever though it was pretty darn crowded.
  • The Ferris Wheel in Seattle–It was like $20 a person, but every vacation needs a cheesy splurge.


As a Bonus, Here’s My Random List of Suggestions

  • Make sure you know ahead of booking a car if your current car insurance has rental car coverage. We didn’t know and ended up paying way more than we needed to.
  • Fill most of your time doing free (or very cheap) things that are unique to each place you visit (state parks, walk through unique urban areas, etc).
  • Christmas Day is not a slow travel day. It was cheaper, but just as busy as any other day.
  • Selfie sticks make sense on road trips. Look, I hate them too, but when you’re constantly in awesome locations without people around, they are a really great way to get pictures of you and your travel partner.
  • If you can find a Bed and Breakfast to stay at, do it. We stayed at one called, The Historic Requa Inn in Upper California and it was incredible. It was a highlight of our trip.

And finally, some shameless pics from our trip to further inspire you: