weather
Sub-10 In The Downpour
The monkey park hike was posted as 20 minutes. In full typhoon rain, it took under 10.
June 25-26
Osaka And The Waldorf
Osaka begins with drenched shoes and turns into the Waldorf being exactly as good as expected, which is still a fairly ridiculous sentence.
Train to Osaka, a ridiculous Waldorf arrival, Marcus, luggage that beat the clock, pool robes, Peacock Lounge, Canes and Tales, 15-course sushi, breakfast celebration treatment, rainy-day Uniqlo merch, bag-over-head clothes shopping, a Devil Wears Prada shoe, British pub Guinness, Dotonbori snacks, and a sake/facial split-up.
High-end, funny, celebratory, and slightly unreal.
Days
How this stretch unfolded.
Thursday / 2026-06-25
Kyoto Rain To Osaka Luxury
The day starts in typhoon rain and ends with skyline drinks, dry shoes, and the nicest hotel the group has stayed in.
Typhoon rain, Arashiyama bamboo forest, a sub-10-minute monkey park hike in a downpour, train to Osaka, Waldorf arrival, room upgrades, Peacock Lounge, Canes and Tales, and 15-course sushi.
arashiyama rainmonkey parkwaldorf roompeacock lounge view
Friday / 2026-06-26
Waldorf, Dotonbori, And Wagyu
Breakfast came with plate art and a hand-drawn card. Then Osaka supplied custom merch, Guinness, Dotonbori snacks, the first group split-up, and a ridiculous dinner.
First Waldorf breakfast with happy birthday and happy anniversary plate messages, then a hand-drawn anniversary card from the staff, followed by Uniqlo custom shirts, British pub Guinness, Dotonbori snacks and Glico Running Man, the first split-up for sake tour and facials, and a wagyu kaiseki dinner with a matcha tea ceremony.
breakfast platesanniversary cardwaldorf breakfastuniqlo custom shirts
Chapter Moments
hotel
Dyson Shoe Recovery
Drenched socks and shoes met the Waldorf Dyson blow dryer. The shoes came back completely dry.
hotel
Canes And Tales
After Peacock Lounge, the night continued with a speakeasy-style hotel drink at Canes and Tales.
family
Hand-Drawn Anniversary Card
At the first Waldorf breakfast, the staff drew anniversary and birthday plate messages, then brought out a hand-drawn anniversary card.
family
Trip Merch Department
A rainy Osaka morning turned into custom Uniqlo shirts and sweatshirts, because Sarah's 40th apparently needed official merch.
funny
The Shopping Bag Protocol
In Osaka, Sarah had to put a bag over her head to try on clothes, because even retail has plot twists.
hotel
The Prada Shoe
The Waldorf had a Devil Wears Prada shoe signed by Meryl Streep and Anne Hathaway after being signed in Tokyo and brought to Osaka.
food
Guinness And The US Game
A British pub stop in Osaka meant Guinness and a few minutes of the US World Cup game, which is either international travel or a sports bar scavenger hunt.
food
Dotonbori Snack Circuit
Dotonbori delivered 10-yen-shaped cheese waffles, the Glico Running Man, and melon bread with ice cream. Balanced meal, if the balance is chaos.
family
First Split-Up
For the first time, the group split: Caitlin and Zach to a sake tour, Ashley and Sarah to facials, then everyone regrouped for wagyu kaiseki.
food
Wagyu And Matcha
The wagyu kaiseki dinner was phenomenal, Sarah said maybe best meal of her life, and the main owner let Zach do a matcha tea ceremony.
funny
Not A Bento Box
In a photo where everyone held bento boxes, Zach held Tokyo Bananas. Sarah's friend delivered the ruling: guy in the middle does not have a bento box.