This First Timer’s Trip to Tokyo:
Where Jazz Bars & Temples Collide
Despite all the YouTube vlogs, Reddit threads, and obsessive research I did before this trip… nothing — no. thing. — could have prepared me for Tokyo.
It’s beautiful. Overwhelming. Confusing. Frustrating. Inspiring. And truly one of the safest, cleanest, kindest places I’ve ever walked around in.
Also? There are adorable cartoon characters greeting you in every possible situation. It's like being gently supervised by cuteness at all times. 🐭🐰🐻
I’ll break down the points scheme for getting here at the end!
Am I dreaming? Maybe. Let’s go.
WELCOME TO JAPAN! Right before walking through customs, I could already tell I was going to vibe with this place.
Especially because — and I’m not proud of this — our first breakfast in Tokyo was at Denny’s.
Ok, but hear me out! It’s a thing here! Locals love it. Plus it’s cheap as hell, so there’s that. And those cute catssss-uh! God! But that iPad ordering system was one of many challenges that scrambled our brains across this lovely country.
Senso-ji Temple at Sunrise: Tokyo’s oldest temple. Built in 645 AD. Yes, 6-4-5. 🤯
Use your jet lag to your advantage: Go early to beat the crowds! Usually, this place is overrun with people but there was barely a soul before 8 am. Once you get there:
Purify your hands.
Draw your fortune.
If you get bad fortunes? Do not sweat it! Tie ‘em up and leave them behind.
Poof. Gone.
Don Quijote: My Overstimulating Wonderland
Five floors of neon-lit chaos! Snacks and socks next to luxury watches next to Pikachu plushies. I loved it so much! I looked for any excuse to go there throughout the trip to buy beauty products with kawaii characters on the packages because inside, I am nothing but a very fancy child.
First lunch in Tokyo?
The Peanuts Café OBVS. It’s the only reservation I made ahead of time in the States, using their website entirely in Japanese. It was good, but little did I know about the Snoopy culinary delights that awaited me in Kyoto.
In the meantime, we had the cutest lattes of all time.
That wasn’t the only adorable meal. I had to bite my fist just to keep from screaming at the robot cat waiter, named Bellabot, at (the aggressively-American-named restaurant) Jonathan’s.
As usual, I stopped to meet dogs. This is Reese. I didn’t get his whole story because language barrier, but he was divine.
Shrines, Shops, and Shibuya: Full-On Tokyo Tourist Time!
Imado Jinja: The kitschy and quirky shrine to lucky cats and relationships. May every wish hung here come true. ✨
Meiji Jinjo’s sake barrel wall. Sadly just for looking, not for tasting.
Harajuku Chaos! On Takeshita Street!!!1!ajkldfh adjh via!!!!!
Shibuya Scramble: Obviously. We are tourists after all.
Tokyo at Night: Jazz, Bluegrass & Snow
My personal peak moments in Tokyo: Japanese takes on American live music.
First: To Hub for Silky Bullets — a Japanese cover band playing everything from Billy Joel to Be Our Guest in Japanese. It was a shock to the system to hear Piano Man performed live without the crowd singing along, but I had tears of joy in my eyes anyway. Below, we got Singing in the Rain, complete with umbrella. Charmed my friggin face off.
Then: We stepped in to Rocky Top, a teeny tiny bluegrass bar that’s about the size of a studio apartment.
These two gents, who go by the name Holly Tango, were excellent musicians with an authentic love of bluegrass and country music.
For most of the show, we were two of three people in the audience. Almost heaven…
And while it was kinda secondhand, hearing jazz piano music flowing into the street while waiting for our uber-ordered taxi in the snow? A mental snapshot that will stay with me for life.
Little Things I Loved
The 3D cat billboard in Shinjuku. Duh.
This particular glass of Prosecco courtesy of the sweet girls at Jet Set Blow Dry Bar. Offered kindly after getting MASSIVELY lost trying to find them. (General note about Japan: You WILL get lost)
This sign outside the men’s bathroom at the metro celebrating the cleanliness of the toilets. Translation courtesy of your most used app in Japan, Google Translate.
Is Tokyo Overwhelming? Here’s What Helped!
I mean, yes. Can’t sake-coat it. But here’s some quick and easy tips for managing it:
Google Translate / Google Maps. Have these bad boys on your front phone screen. For an even slicker move, place them on the lower right (or left) corner of your phone screen so they can be reached the quickest.
Take your time. Don’t force yourself to see every little Instagrammable location. You won’t succeed and you’ll just wear yourself out. Build in rest times where it’s just you with an egg-salad sandwich from 7-11 (an addictive Japan must!!) in your hotel and your native Netflix.
Uber app! At least twice I went the wrong direction on the metro or bus. Instead of panicking, I summoned an inexpensive cab with good ol’ Uber and they were there in minutes.
After four days of awe, chaos, jazz, snow, sweet locals, and the cleanest public restrooms I’ve ever seen... we were off to Osaka for a very quick 24-hour adventure before landing in Kyoto.
Stay tuned!
Points n’ Stuff:
Using Roame.travel, I put in alerts for flights to and from Tokyo.
Japan Airlines business class LAX-NRT - 75k each via Alaska Airlines. I had a signup bonus for 90k miles through Alaska’s Visa card and purchased the remaining points on sale for about $800.
Singapore Airlines business class NRT- LAX - 75k each via Aeroplan. Since there was a transfer bonus from Chase, I was able to get both seats for 100k total.
Hotel: Monday Apart Premium in Asakusa, paid with cash. A darling little hotel in a quiet but convenient spot that gave us an apartment-sized room. Cheap and cheerful, would like to live there.
Mistakes were made: I initially booked an Air B&B but we did an about-face because it was not nearly as cute or cozy IRL. Cut to me frantically scrolling Booking.com for another place and us rolling our luggage through city streets. Bless the hosts for letting us get our money back. It pays to be kind to when traveling, even when you’re not satisfied.
