2019 Road Trip Superlatives

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Jake Cain is an entrepreneur and writer from Cincinnati, Ohio. He spends his free time driving around the country in his late 90’s conversion van, affectionately known as the “Monster Van” with his wife and 3 boys.

We’re back from our trip!

Today, I drove my Honda Odyssey for the first time in a month and I felt like I was driving a high performance sports car after driving the Monster Van for 30 days – which is kind of like driving a mechanical elephant.

I’ve got some city by city blogging to catch up on now that I’ve got some more time, but I thought it’d be fun to do some superlatives.

If you’re not familiar, superlatives were those things in school where you voted for who’s the most likely to succeed, best dressed, etc.

This is kind of like that, but for a vacation.

Let’s jump right into it.

The Most Amazing Thing I Saw

Night Sky

When you’re fortunate enough to take a trip that includes so many natural wonders, there are going to be moments where you can’t help but say “Wow!

On my 2017 trip, my #1 “wow moment” was walking beside the sequoia trees in California.

The enormity of them is something that simply can’t be appreciated until you see them in person.


We saw the sequoias again in 2019, but my number #1 wow moment this year was undoubtedly the stargazing at Bryce Canyon National Park

The picture above isn’t one I took – my iPhone attempt was comically bad.

But I guess I’ve always thought photos of night skies like that were doctored up somehow.

Kind of like when you see real estate photos on Zillow and think “that house is so spacious!” then you show up and the living room is the size of a walk-in closet.

So I expected it to be cool, but not “better than all the pictures” cool.

Astronomy Festival

Something I discovered a couple of weeks before we left is that we were visiting Bryce Canyon during their annual Astronomy Festival.

This wasn’t great scheduling on my part – just a bit of good fortune.

It turns out we were there on the new moon, with basically the perfect conditions for stargazing. They also had special programs for those few days where they set up high powered telescopes and shuttled you out into a field for optimal viewing.

Again, I was exiting the bus expecting it to be really neat.

But when I stepped off that bus and looked up, it was almost an involuntary reaction to say “woooow!

It was honestly an overwhelming, awe-inspiring, and somewhat spiritual experience.

I’ll give a more complete rundown why stargazing in this part of the country is so different than others in my Bryce Canyon blog post.

But for now – just know that dark sky stargazing should be immediately added to your bucket list.

The Best Thing I Ate

This is a difficult award to hand out.

If you’re familiar with our family, you’ll know that we take eating very seriously.

My dad and I once went to a minor league baseball game simply because we were curious about the Krispy Kreme burger.

At many destinations, eating isn’t just part of the experience – it is the experience.

I spent many hours scouring the internet and mapping out many lunches and dinners in our cities along the way – so we had a bunch of delicious food on this trip.

With that said, the best meal I ate was at Jack Stack Barbecue in Kansas City.

Jack Stack Barbecue

Of course, when you’re going through Kansas City it’s not really a question of “should we eat barbecue?”

It’s more a question of “which barbecue place should we go to?

(If you disagree, unfriend me on Facebook).

We almost went to rival pitmaster Joe’s Barbecue which might have been my favorite meal on the 2017 trip – but it had a line that you’d expect to see at Kings Island, not a lunch spot.

I’d penciled in Jack Stack originally, so I took the long line as a sign that I should venture out and try one of the other icons in KC barbecue.

I had the burnt ends & ribs combo with their baked beans and cheese corn for a side. I also tried their heavenly cornbread along the way.

Everything was out of this world. In fact, it was one of those meals where you catch yourself making the “mmmm” noise intermittently while chewing.

That said, I’d like to do a more hands-on, in-depth review process before declaring my favorite Kansas City barbecue restaurant. So until next time…

Where I’d Like To Go Again

The answer to this one is “pretty much everywhere.”

But it seems like there’s always a place or two that really stands out as somewhere you’d like to come back to and spend more time.

Honestly, that’s one of the things I love about the “sampling America” idea of seeing a bunch of places in a relatively short amount of time.

Perhaps like many of you, we are guilty of finding a vacation spot we like and then going there year after year.

I always thought it would stink to go somewhere for the first time when you’re 68 years old and think “Dang it! We should have been coming here our whole lives.”

However, it also feels kind of risky to book a week at a place you’ve never been before.

So I love getting a 1-2 day whirlwind tour on these trips and then (hopefully) finding places we’d like to come back to and spend more time.

Zion National Park

This year I’m going with Zion National Park in Utah as the top place I’d like to go back to.

For whatever reason, it was much more beautiful than I thought – and I really want to tackle the famous Narrows hike.

Zion Narrows

You’re basically in water the entire time and need some special gear – so it was a little more intense than we were could have handled on this trip.

But I took the riverside walk and got a glimpse of the beauty, so I’ve earmarked this as one I’d like to do when the boys get older. (I’ll also likely invite a really outdoorsy friend like Jonny Carroll to join us so we don’t accidentally die).

The Place(s) I’d Never Go Back

Never is a strong word…

But there were a couple of places I’d never put back on a trip itinerary and travel to on purpose.

One is the Crazy Horse Memorial.

You can read more about why it’s lame here.

Crazy Horse

In short, Crazy Horse is a place you go because it’s close to Mt. Rushmore and there’s nothing else close to Mt. Rushmore.

The problem is, Mt. Rushmore is about 100X better – so Crazy Horse just seems like a comparative letdown.

The other one was Four Corners.

I’d never heard of Four Corners.

Apparently dad had heard all about it, and was really excited to take a picture where we were standing in 4 different states.

It’s the only spot in the US where 4 state lines intersect – Colorado, New Mexico, Arizona, and Utah.

Here’s the obligatory photo:

Four Corners

I’ll share more when I complete my full write-up for that day – but the long and short of it is that it’s in the middle of nowhere, costs $5 per person (even if you’ve got a bus), and is surrounded by what seems like a Native American flea market with no electricity or plumbing.

Needless to say, I’ll never get that hour of my life back…

The Best Place We Stayed

Most nights we were staying in the La Quinta’s and Comfort Inn’s of the world.

But, we did stay at 3 places that really stood out from the crowd.

  1. Trump International Vegas
  2. Teton Mountain Lodge & Spa in Teton Village
  3. Red Cliffs Lodge in Moab, UT

They were all amazing for different reasons, but #1 on my list is the Teton Mountain Lodge & Spa.

Here’s a couple of pictures I took in and around the hotel:

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Kids at pool

Not pictured: me enjoying the complimentary access to the steam room in the men’s spa locker room.

It’s a skiing village, so probably during skiing season it wouldn’t be such a great deal – but for summer time, we were able to get this 2 bedroom suite at a high class property for a similar price to getting 2 basic hotel rooms in Jackson, WY (which was high season pricing).

Put this place on your radar if you’re headed to the Tetons and thank me later.

The Funniest Thing That Happened

When you’re on the road with our family, there will be plenty of laughing.

Narrowing down to a funniest moment is tough – but I think one fateful evening near Big Sur on the Pacific Coast Highway takes the cake.

We had pulled into a parking area across from the famed overlook, Mcway Falls.

It was completely packed and we were running out of daylight with a chunk of driving left – so we decided to let the small-bladdered among us hit the restroom before jumping back on the road.

I parked for a moment, but then pulled the van up near the bathrooms to save my mom a few steps.

Getting into the van was a bit of a process for her, and I noticed that I was blocking traffic while she was making her way up the step into the backseat.

By the time she got in, she realized a set of headphones had fallen out into the parking lot.

So back out of the van she went.

Then it was time to climb back in.

The cars behind me weren’t honking their horns (yet), but I was feeling the pressure to move.

So the second mom got in and shut the door, I said “here we go!” and threw the van into drive and released the brake.

Our inclined position on the road made for a quick jolt, which immediately tossed mom into the floor.

Hudson was temporarily in the captain’s chair – so mom fell across his lap and was firmly wedged between the seats. Hudson was yelling “get off!” which didn’t really help matters.

She wasn’t hurt – but was laughing uncontrollably, which meant she was in no condition to lift herself up and back into a seat.

At this point I was back cruising PCH, so I couldn’t really stop the van.

Eventually, she found her way off the ground and back into the seat. Everybody was laughing so hard that we didn’t get a chance to snap a picture.

Fortunately, Jackson took a mental photograph and sketched this reenactment:

Nana falling

Moral of the story?

When I say “here we go!” you should grab a seat immediately, if not sooner.

The Most Random Coincidences

I’ve got 2 for this one…

First was when I was browsing a store/restaurant area in the Canyon area of Yellowstone when I saw my old work buddy, Vishal Saboo.

Jake Cain Vishal Saboo

We worked together for years at Hobsons, and Vishal was/is one of the guys that everybody likes.

I hadn’t seen him in years and found out that he took a job that moved him to the bay area – which makes our meet-up even more unlikely.

I became aware of random coincidence number 2 after the fact…

I got a Facebook message from an old friend, Steve Daniel. He’s much older than me (my sister’s age) – and he let me know that he’d also been in Jackson, Wyoming for a few days.

After a few messages, we discovered that we’d stayed in the same motel on the same night in Jackson, WY.

There are tons of places to stay in Jackson, and of course being from Cincinnati – ending up in the same hotel in Wyoming isn’t exactly like bumping into a friend at Skyline in Mason…

Anyway, we didn’t actually see each other – but I found that to be pretty crazy.

If I Only Had One Week…

It’s not lost on me that we’re incredibly privileged to be able to take 4 weeks off and travel.

For most Americans with a somewhat “normal” job, this is nearly impossible to pull off.

So I don’t know if this counts as a “superlative” but if you want to plan a little “sampling America” trip of your own and see the maximum amount of cool stuff, here’s what I’d pick:

San Francisco, Yosemite, Pacific Coast Highway. 

You can cram many of the major highlights into a week if you could fly round trip to San Francisco. Here’s why it would be an amazing week for just about anybody:

Classics & History

If you’ve never been to San Francisco, take in the obvious things like the Golden Gate Bridge, trolley cars, and Lombard street. Then, enjoy some of the history – like Alcatraz and The Walt Disney Family Museum (if you’re a Disney fan like us).

Mountains, Waterfalls & Giant Trees

Once you’ve done 2 days in the city – stay somewhere between San Fran and Yosemite (about a 4 hour trip). You’ll see the so-beautiful-it-looks-fake overlooks like tunnel view (below) and many others.

Tunnel View Yosemite

Then, take a hike to one of the many incredible waterfalls. Finally, spend some time at Mariposa Grove and get up close to some of the biggest trees in the world – which are guaranteed to blow your mind.

Beaches, Oceans & Sunsets

I’m spitballing this agenda a bit, but if I had a week I’d head back toward the coast after Yosemite and spend a day driving down the Pacific Coast Highway. At the very least, go through Big Sur and if you’re a golf fan – do the 17 mile loop drive through Pebble Beach and step out into the Pacific Ocean near Carmel.

PCH Big Sur

Assuming your return flight is from San Francisco, find a good stopping point and make your way back – winding along some of the most beautiful coastal driving you can imagine.

Runner Up…

If that doesn’t sound appealing and you’re more into red rock types of scenery – I’d find a flight to Utah and stop by some of their national parks like Zion, Arches, Bryce Canyon and Canyonlands.

When in Moab, don’t stay anywhere besides the Red Cliffs Lodge.

Red Cliffs Lodge

Wrapping Up

If you’re reading this – thanks for following along with our trip!

I really appreciate all the comments here and on Facebook – it’s been a lot of fun.

In the coming weeks, I’ll be going back through notes and photos and filling in some of the places I’ve missed – so hopefully you’ll keep reading and pick-up some tidbits to use on your next journey out west.

18 thoughts on “2019 Road Trip Superlatives”

  1. Great read! I’m so happy for you guys! I’m glad your mom’s alright. I can hear her laughing! Somehow I knew the funniest moment would somehow have your mom involved. Lol

  2. “The Funniest Thing That Happened”
    Tears rolling down my face. Thank you Jackson for such a great sketch the event.

  3. Thank you for taking the time to share your comments regarding your vacation trip.
    I will certainly follow your recommendations when we make our trek to those areas.

  4. You did a great thing Jake with this road trip, and the fact that you included your parents speaks to your family character. Next time, we can get a larger van and Jan and I will venture out with the notorious “Cain Gang”. Enjoyed.

  5. Jake, nice summary!
    Thanks for taking the time to include all of us that followed you and your family on your amazing adventure.
    It became a daily routine to “let’s see what the Cain family did today or yesterday”. The photos and descriptions were great – you have a excellent talent Jake! And I must say, what a wonderful gesture it was dragging Dale and Thelma along with your family – wonderful memories that will last a lifetime for the entire Cain family – parents are special! Oh my goodness Thelma, I thought everyone knew what “here we go means”! Thank goodness for Jackson’s artistic talent!

    Thanks again for sharing!

  6. Loved this superlatives overview. Look forward to the next posts. I went to school in Monterey, and spent lots of time along the PCH and 17 mile drive. Nice area, but pricey.

  7. What a wonderful trip all of you were privilege to take,I enjoyed every moment of your sharing with all of us.Your family has always had a special spot in my heart.I missed all of you especially your mom she is more like a sister to me than a good friend.Glad you are all back home safe & sound after a trip of a life time.Love all of you,see you soon.Thanks again for all the pictures loved them especially the one of Thelma that Jackson drew lol You have the cuties boys.

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