10 days in Japan with my sister: Tokyo, Osaka and Okinawa (an honest first-timer guide)

Aerial view of Shibuya Crossing in Tokyo with crowds crossing

Ten days in Japan with my sister was exactly what I needed after a STRESSFUL year. Three cities, one sister and a whole lot of catching up.

Now you’re probably asking, isn’t Japan expensive? Real talk: ours was on the higher end. WELL, some trips are about the budget, and some trips are about the people. This one was about my sister.

Aerial view of Shibuya Crossing in Tokyo with crowds crossing
Shibuya Crossing from above. Yes, it’s as chaotic as it looks.

Why we went

After the year I had, I didn’t want a checklist vacation. The whole point was to move slow, decompress and reconnect with my sister. No trying to see every single thing. Just time together.

If you take one thing from this post, take that. Slow counts as a plan.

Our route: Tokyo, Osaka and Okinawa

We had 10 days total: 5 in Tokyo, 3 in Osaka and 2 in Okinawa.

  • Tokyo: the big-city energy (and the best night out of the trip)
  • Osaka: the shopping stop
  • Okinawa: the spa, the slow days and the full exhale

Tokyo: a music bar, Kehlani and a very small world

The most fun night of the whole trip? A music bar in Tokyo where my sister and I ended up singing Kehlani hits. Across the world. In Tokyo. Wut. If you know, you know.

Globalization is EVERYWHERE, Queens. You can fly halfway around the planet and still find your people through an R&B chorus.

Outfit photo: white tee, yellow sweater over the shoulders, navy pinstripe shorts and a cream quilted bag
Evening fit in Tokyo.
Outfit photo in a hotel elevator: cream button-front vest, wide-leg cuffed jeans and white split-toe flats
Day fit for walking the city.

Osaka: come with room in your suitcase

Osaka was our shopping stop, and it delivered. Was all of it necessary? Let a girl live. Pack light on the way there. You’ll thank me on the way home.

Heads up if you’re going soon: Japan is changing how tax-free shopping works for tourists starting November 1, 2026. Instead of skipping the tax at the register, you’ll pay it at checkout and get it refunded before you leave the country. Keep your passport handy and hold on to your receipts, and check the official Japan travel site for the latest details before you shop.

Okinawa: the spa that made the whole trip

The spa in Okinawa was my favorite part of the entire trip. After the year I had, my body said THANK YOU.

What made it so good: it was wellness-focused and used ingredients from the island itself, including the seaweed wrap I booked. Local ingredients, zero rushing, full decompress. 10/10, no notes.

The pro tip that got us our best meal

The restaurants all over social media come with long lines and a meal everyone has already posted. Instead, have your hotel concierge or your credit card’s concierge service (if your card has one) help you book places that AREN’T all over your feed.

That’s how we ended up at a speakeasy-style restaurant that wasn’t on anybody’s list. It blew. Our. Minds.

What it cost (the honest version)

Japan was on the higher end for us, and I’m not going to pretend otherwise. We picked comfort, a spa day and really good food over squeezing every yen. For a sisters trip after a hard year, that was the right call for us.

The total: about $7K for 10 days. Not a budget trip, and I’m not going to dress it up like one.

First-timer tips I’d give my little sister

  • Pick fewer cities or stay longer in each. Rushing is how you come home needing another vacation.
  • Use a concierge for reservations. Your hotel or card can get you into places the lists haven’t found.
  • Leave empty time in the schedule. The slow moments ended up being the best ones.
  • Know the tax-free shopping change. From November 1, 2026, you pay tax at checkout and get refunded before you fly out.
  • Budget for the splurge that matters to you. For us, that was the spa.

The real lesson

Take the time. Move slow, decompress and go see the people you love. The to-do list will survive without you for a week or two. (Ask me how I know.)

xo, Malificent

written by your big sis

Hey, I’m Malificent.

Startup operator, recovering burnt-out W-2 employee and freelancer. I write about the stuff I had to learn the fast, messy way: startup life, landing clients and getting your money right.