Spyplane Ultimate TOKYO Guide 2025
The slappiest food, shops, drinks, sights, lodging & more
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We just completed a monumental Japan Recon Mission. On our second day, Erin and I (Jonah) popped in on the Tokyo headquarters of Auralee, where designer Ryota Iwai took a break from dialing in his Spring 2026 collection to come say what’s up. “Is this your first time in Tokyo?” he asked. We told him it was Trip No. 5, but that we were stoked to see parts of the city, and the country, we’d never seen before.
We’ve written about Iwai’s and his team’s gifts for materials development, silhouette and color, so we were intrigued when he told us he’d just been standing in front of hundreds of Pantone chips, carefully rearranging them, winnowing them down, considering different juxtapositions, eliminating what felt wrong, chasing what felt right. Other designers might work from a set of clear references — the costumes in a favorite movie, say, or the flora of a beloved landscape. But not Ryota, who, it turns out, chooses colors by looking at colors, following the chromatic vibrations where they lead him.
In much the same way, when we travel to cool places to create Ultimate City Guides for you, we proceed from our own highly developed vibrational compasses, which always point us toward True Norths of Travel Delight. We also rely on recommendations from a tight brigade of tasteful friends.
Japan is a top destination for us and Spyfriends alike, and these days it’s measurably more popular than ever. Our inaugural Wonders of Tokyo Guide, from fall 2022, was an instant classic. It’s no exaggeration to say it reshaped the way an elite swath of cool visitors navigate this sprawling, dense, wonderful city. Every recommendation in that report remains golden, but we knew it was time for a brand-new 2025 Spyplane Guide to Tokyo — plus brand-new recon on other destinations: Kyoto, Osaka, and a clutch of deeper-cut locales we’d heard were sick but never had the pleasure of visiting before.
For three weeks, we zigzagged between cool cities and beautiful stretches of countryside, great shops and wonderful bars, top-notch lodging, delicious restaurants, fantastic museums and transportive gardens.
We ate tremendously, beheld outsize beauty, averaged 18,000 steps a day — and took notes and photos of everything, so you can do it, too.
Other guides from the trip are imminent. Today we’re thrilled to unveil the Blackbird Spyplane Ultimate Tokyo Guide 2025.
We’re grateful to ourselves for being great at recon, and we’re grateful to the illustrious Spyfriends whose recommendations helped make this trip to Japan our most satisfying one yet, including:
Ryota and Joshua from Auralee, Yuji from Ernie Palo, Shinya from Maidens, Dan from James Coward, Oliver Church, Toshi from Cottle, Keith from Henry’s, Alex from A. Presse, writer, photographer, kissa expert and 20+ year Tokyo resident Craig Mod, Evan Kinori, Akari Tachibana, Dan from Bar Part Time, Ezra Koenig, Chelsea Jones, Adam Wray, Becca Rosen, Robin and Rosalie at Heath Ceramics, Nur from Gnuhr, Natsuko from Goldwin 0, and all the tied-in locals who blessed us with gems along the way. Of course we have to shout out the bustling Tokyo thread in our Global Intel Travel Chat, too.
Enjoy!
— Jonah & Erin