I’ve never really thought of myself as an adventurous person. I’m generally quite conservative about my life decisions and will choose the path of lesser resistance. A few months ago, the idea of driving from Boston to San Francisco was planted in my mind. Without really thinking about it too much, I decided that it sounded great and I really wanted to do it.

That’s about 4,000 miles, or 60 hours of driving, according to Google Maps. I definitely saw the numbers and did the math but, in retrospect, I certainly didn’t fathom the reality of it. I played around with the drag and drop function and pinned different cities onto the route, sharing different possibilities with my partner in crime (henceforth referred to as PIC) every so often between February and April. We would start out in Boston and head up to Toronto then go west. I wanted to see Mt. Rushmore, the Grand Canyon, and everything else in between. (To be honest, I didn’t know what there was in between. I just assumed there would be something.) Before I knew it, the dates were set. We would leave Boston on May 16th and we would arrive in San Francisco by the 28th, with a few days at home in Toronto.

This may also be a good time to note that our mode of transport was a Prius. For days leading up to May 16th, I’d wake up in the middle of the night panicking about whether all of our boxes and luggage would fit in the Prius. By the morning of the 15th, I was antsy to get all of our things loaded up. (To put it plainly, we had a lot of stuff. Boxes, bins, suitcases, and a bike.)

And so we road tripped.

On the morning of the 16th, we wake up bright-eyed and bushy-tailed and extremely optimistic. Then we realize that we have forgotten to account for where we would put our backpacks. We also have an extra laundry basket of things to drop off at the PIC’s house… The backpacks end up squished delicately into small crevices and the laundry basket sits snugly on the PIC’s lap while I drive the first (40-minute) leg of our journey to the PIC’s house. After unloading some items and having some parental experts rearrange the car a bit more, we are really off on our way in the big, bad world.

Now, I won’t go into detail about each and every toll booth, meal, drink, snack, pee, and scenic stop we make along the way. The road trip map we keep does that pretty well (minus toll booths and pee stops). We quickly learn on that first day that rest stops aren’t very well spaced out and also that it’s extremely pleasant to trade off driving frequently.

Highlights of Day 1:

States visited: Massachusetts, New York (2)

  • Make it out of Boston
  • Pit stop at the PIC’s to drop off some extra baggage
  • Lunch in Syracuse, where we are uncertain whether we need to pay for parking in the meters or not (the signage says yes but a municipal worker who passes by tells us not to…)
  • Realize that we actually have to gas up fairly frequently (since the Prius has such a small gas tank)
  • Successfully enter Canada and eat Tim Horton’s (Nutella donuts!)
  • Find crazy drivers in Ontario, whereas we thought that Massachusetts driers were bad (see: Massholes)
  • Eat our first homemade meal in ages once we arrived back in Toronto

We spend the next few days in Toronto, indulging in good food, exploring downtown, and discovering that Toronto is incredibly hipster in certain areas. (“It’s like we’re in Brooklyn!” I quote.) We are lucky enough to catch Victoria Day fireworks and enjoy a 19+ VIP movie (Avengers) at one of the new fancy theatres. And, of course, we have our first burgers of the trip. (Burgers are important because we had launched a cheeseburger campaign, soliciting fiscal support for our nutritional needs as we embarked on our trip. The deal was that for each $5 sponsorship, we would send out a postcard to our sponsors. We also upped it to two postcards per person for the first ten sponsors. We later realized that it was a financially questionable move as we ended up spending a good amount on postcards and stamps, but eventually concluded that sending postcards is so much fun that it’s definitely worth it. If you’re interested in sponsoring our salad campaign on the way back, please let me know.)

Oh, also, at some point of all of this, we revamp the route. We take out Mt. Rushmore and decided to do it on the way back. (Because what goes to San Francisco from Boston must eventually return to Boston, so…that includes us and the car.) Instead, we route from Toronto to Chicago then through the Midwest to Texas/Arizona/New Mexico and then through to California via Las Vegas. (We later discover that this is basically Route 66, except for the Vegas detour. Guess we aren’t as original as we thought after all…)

Anyway, let me skip forward to the official Day 2 of the road trip. This brings us to Thursday, May 21st. (Reminder: at this point, we have a week to get to San Francisco.) We start out quite early again and this time set the goal of Chicago by dinnertime.

Highlights of Day 2:

States visited: Michigan, Illinois (4)

  • Depart Toronto
  • Return to America successfully through Windsor-Detroit
  • Visit PIC’s birthplace in Detroit
  • Explore Ann Arbor and the university campus
  • Somehow make it to Chicago by dinnertime
  • Get misled by Google Maps and exit the highway two exits too early and spend 45 minutes in rush hour downtown traffic
  • Visit three parking lots before settling on one that was sufficiently cheap enough (“Okay, okay, there’s one on the next street over that’s $18 instead of $22. Or there’s one that’s $19 on that street.”)
  • Dinner in Chicago’s Chinatown with friends
  • Enjoy a breathtaking view of Chicago’s night skyline

Suffice it to say that certain lessons are reinforced that day, e.g. parking in cities is hefty and rush hour city traffic is downright horrible.

From hereon, the road trip continues pretty consistently. I’ll dive right into the highlights.

Highlights of Day 3:

States visited: Missouri, Oklahoma (6)

  • Go to Springfield, the birthplace of Lincoln, and see enough Lincoln paraphernalia for a lifetime
  • Somehow make it to St. Louis by lunchtime
  • Discover that one can actually go up the Arch, but also that the next available tour time is too late for us to make it (as we have a motel reserved in Tulsa)
  • Eat Subway sandwiches sitting on the steps of the old court house in St. Louis while admiring construction that is blocking our view of the Arch
  • Drive to Springfield (not in Illinois now, but rather Missouri) for dinner and eat at a very American diner
  • Discover that we are the only Asians in the entire restaurant
  • Notice that they are playing Wheel of Fortune on the TVs in the restaurant
  • Realize that everyone in Springfield either drives or is on the street and admiring an old car (hobby car collecting/maintaining?)
  • Manage to somehow get our way to Tulsa while constantly asking each other, “Hey, we’re going to Tulsa…OH KAY?” (Tulsa, OK…get it?)
  • Conclude that cities out here seem to rise up out of nowhere and that it’s bizarre since the land is so flat, you’d expect to be able to see far away (but somehow we can’t?)
  • Also…realize that there’s a point when the car time stops matching our phone times – “Oh my gosh. We just drove into a different time zone.”

Highlights of Day 4:

States visited: Texas, New Mexico (8)

  • Tulsa to Oklahoma City by mid-morning
  • Visit the Oklahoma City museum and memorial
  • Eat lunch on the road…somewhere, somehow
  • Drive, drive, drive, as much as we can, to get to Santa Rosa, NM by night
  • Find ourselves in Texas, because there is a random sliver of Texas that divides Oklahoma and New Mexico
  • Drive through torrential downpours, see some lightning, pretend we didn’t see it, and continue onwards “because we have a schedule to follow, places to be, and people to see” (or something like that… Do I look like I remember what I say?)
  • Detour at one point in pursuit of a taqueria that yours truly finds on Google, only to discover it is a trucker stop and seems a bit too rundown
  • Follow Google Maps to take a local road back to the highway, only to find ourselves driving through a few miles of pretty flooded roads (“Wheeeee! Look at how much water we’re splashing!” “…Wait. Is this bad for the car?” “Guess we should just keep driving…”)
  • Receive an Emergency Alert on our phones, informing us of flash floods in Texas (“This makes a lot of sense now…”)
  • Return to the highway only to discover that our detour was probably for the better because we have narrowly avoided congestion on the highway just before our entrance from a skidded FedEx truck
  • With great anticipation, stop to see the Cadillac Ranch, which we discover is a good distance inland from the road. Luckily at this time the rain has cleared up though it leaves mud and puddles everywhere, which we try to avoid by climbing through a very narrow opening in a massive barbed wire fence that prevents people from driving in to see the Cadillacs
  • Discover that the Cadillacs are actually a public art display (in our words) because everyone just brings spray paint here and paints them. Decide to one day return with spray paint rather than just staring at others spray painting the Cadillacs
  • Arrive in Santa Rosa and discover that the town is literally just motels – not even a drug store or grocery store (according to Google)
  • Sleep early because what else is there to do?

Highlights of Day 5:

States visited: Arizona (9)

  • Wake up early and drive into Albuquerque to meet another friend
  • Discover how excited we are to actually know someone who lives in the place we’re visiting because we’re tired of not knowing any locals
  • Rejoice in the food that eateries near college campuses provide – i.e. we ate at a restaurant that was near the Albuquerque university campus and the food was cheap and generously portioned
  • Learn that New Mexico is known for its green peppers
  • Visit Old Town, which practically feels like vacation, with relaxed music and people ambling around – and no excess of crowds, phew!
  • Realize that it is Memorial Weekend and realize that we have scheduled ourselves to visit the Grand Canyon on a popular outdoorsy long weekend…
  • Drive into the depths of the night in order to make it to Williams, a town at the foot of the Grand Canyon, though our pressing deadline doesn’t stop us from detouring to the Painted Desert and Petrified Forest National Park
  • In short, we go to see some beautiful streaked desert landscapes and some tree trunks/stumps that were turned into “petrified wood,” which is basically rock, as a result of volcanic activity from the dinosaur days (“Wait…we’re going to see scared trees?”)
  • Discover that despite all the souvenir shops we’ve seen on the way, one of us still has a desire to look at all the stores in town (and there are a lot of them)
  • Go to sleep at the oldest hotel in Williams

Highlights of Day 6:

States visited: Nevada (10)

  • Wake up early (I think at this point this must be a given) and drive into Grand Canyon – at this time, there is no line up to enter the park, and for this we are eternally grateful because we had heard about 3-mile long lines the day before
  • Visit a few of the observation points and both realize that: a) the Canyon is greener than we expected, b) we are not as deeply in the Canyon as we had expected to be; when we drive, it feels like we are merely in a park or forest, c) the Canyon is really chilly for some reason
  • We walk around a bit more and decide to hike down one of the trails for a little bit; all the way down are signs that remind us of how frequently hikers pass out or need medical assistance
  • We realize we are very unprepared and commit to only hiking down a little bit, just to get some perspective
  • On the way back up, we realize that the whole thing about not trying to descend and ascend in one day is totally true and also that “going down is optional but coming back up is not” (from a sign)
  • Leave the Canyon feeling satisfied though I am a bit sad that we didn’t get to see the Colorado River from nearby – I totally expected to – and also that the canyon doesn’t look much like what I had seen in movies (like Spirit: Stallion of the Cimarron)
  • Make it to Vegas by 4pm, discover that despite the free parking everywhere, parking is horrendously difficult – also, we skip Hoover Dam because the traffic going into the dam and out looks horrible (I never realized dams could be so popular)
  • Find ourselves in a humid and warm climate, much to our disappointment, as we’ve been dressed for the cold canyon all day
  • Check in to the nicest hotel we’ve stayed at so far – the Planet Hollywood – though ironically it costs about the same as the 2-star motels we’ve stayed at elsewhere
  • Explore Vegas until nightfall, catching most of the major attractions (saving the other side of the Strip for the next day), including a dinner at the Paris Las Vegas’ buffet (Le Village), which is chosen after great research
  • Go to bed feeling stuffed and like good tourists

Highlights of Day 7:

State visited: California (11)

  • In the morning, we eat at Denny’s and then go to the rest of the Strip
  • I declare that there is simply too much sun (“This is a desert, you realize?”)
  • Drive into Los Angeles, see some red carpet and some movie stars for the premiere of some movie, detour to see if we can find where Taylor Swift lives, and then dinner at a small Japanese café
  • Briefly stop at Santa Monica Pier, which concludes the Route 66 portion of our road trip – we spend a good amount of time gazing at the Route 66 paraphernalia and maps and feel pretty impressed at how far we’ve gone
  • Stay at our hotel just north of Santa Monica
  • Rejoice in that we have made it to the promised land – California! We may not be in San Francisco yet, but it counts for something that we’re in the state, right?

We spend day 8 driving up Route 1 through Santa Barbara and to Hearst Castle, then we stay the night in San Simeon. We realize that driving less at the end of the road trip is a good call, as neither of us really loves the driving now. We are also reminded of how we’re most definitely in California now when there are portable toilets at Hearst Castle as the bathrooms have been shut down on governor’s orders. At dinner, we ask for water habitually and realize we are charged 40 cents a cup. The PIC always drinks water while I usually don’t – this particular meal, I make sure to drink every last drop of my water. I decide that henceforth I will try to remember not to get water.

The next morning, we wake up at a more humane hour than we have been previously. We drive up the highway (instead of the coast) to San Francisco, as the previous few days have showed us that Route 1 is very curvy and drawn out…one cannot drive very quickly on the roads. To do the scenery justice, we decide that we will probably go to Big Sur and cover more of Route 1 on a weekend trip out from San Francisco, so we just get to the city as quickly as we can.

We make it and are met with the dilemmas of parking somewhere near the apartment so we can unload the car though we also need to settle on a monthly lot. We also have to meet the realtors for the keys and we have yet to feed ourselves lunch… But the whirlwind of move-in logistics is a story of its own.

All in all though, we survive the road trip. We learn to drive better, we deal with unexpected weather, we have pretty good discipline (in bed by 11, up by 6 or 7), and we manage to see a lot more than I would have ever expected. We go to eleven states and many more cities. We visit two national parks. We visit quite a few memorials. We do a good mix of city and nature sightseeing and we probably purchase over 40 postcards. We listen to almost all of Harry Potter and the Half Blood Prince on audio tape. We probably spend over 70 hours in the car. We unsuccessfully parallel park a whole bunch of times and we also successfully do it a few times as well – credits to the PIC for parallel parking. And somehow, through all of this, we manage to still conclude the trip with a smile on our faces and a smile for each other.

What do I learn? That there is so much to be seen. That the middle of America is often forgotten and that even just seeing the different landscapes is fascinating. That there are so many places I want to revisit from this one trip. That apparently it’s possible to cross time zones by car. That we have actually made it from the Atlantic to the Pacific. That Priuses can make it on highways.

More importantly, though, I learn that it is valuable to not overthink certain things. Don’t take me wrong – I certainly think that road trips require a lot of planning. I think it was good that we had nightly goals of where to arrive and that we booked hotels a few days in advance so we always knew where we’d end up each evening. What I do mean, however, is that I realized I may not have embarked on the road trip if I had thought too much about the logistics and the realities of driving eight to ten hours a day. I probably would have gotten scared and decided against the road trip. A derivation from my norm gave me one of the best adventures of my life and I’m only halfway through it – the return trip still remains.

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cheesebooooger 2.0
Image credits to the one and only Kat Dai <3

Isabella and Eric are embarking on a cross country road trip.
The plan is to depart Boston on May 16 and arrive in San Francisco on May 28.

Follow us along our adventure here!

If you’re interested in sponsoring a cheeseburger/veggie burger for us, we will send you a postcard in appreciation.

$5 to either Isabella (isabellajchiu) or Eric (ouyang) on Venmo
= 1 cheeseburger or veggie burger
= postcard mailed right to your door. (Just specify your address when you Venmo us.)