One of the biggest drivers for me quitting my job was the fact that my sister, Molly, and her family (husband + 3 young children) moved to Tokyo, Japan in summer 2023. They had previously lived in Brooklyn, NY and I managed to visit there twice a year. But now they were moving halfway across the world! Luckily for me, Tokyo is one of my favorite cities in the world, having visited twice (in 2016 and 2019) and loved it both times. I’ve often thought I’d be happy living in Tokyo and to be honest, I RARELY think that about places I visit. I mean… I don’t even really enjoy living in LA that much LOL

I regret not seeing Molly’s kids more often when they were really young. As I learned by watching Rose (6 at the time of this writing) change SO much between my sporadic visits, kids grow up really quickly! And I want to be there to experience more of their young lives before they start thinking I’m a lame adult. Or… let’s be real, before they just sit in their room reading and aren’t fun for ME to hang out with anymore. I jest… kinda. Anyways, last summer I started thinking — how am I going to see these kids at least 2-3x per year with this full-time job of mine? And then I remembered that I’ve been saving money for years, dreaming of eventually taking an “adult gap year” or “sabbatical”. There is never really a GREAT time to quit your job soooo my sabbatical began 10/13/2023. What started as a 3-6 month plan has morphed into a 6-9 month plan, but thus far, I have no regrets and no plans to rush back to work.

Tokyo is an incredible city and has such an insane mix of Times Square-like chaos and absolute peace and serenity within the parks/ temples/ gardens scattered all over. There are SO many things to do in Tokyo. It’s clean, safe, and efficient. It has incredible food, a great nightlife scene, and the cutest stuff you don’t need to buy but probably should. The public transportation runs on time. People are generally polite. Not much English is spoken, but with enough basic Japanese vocabulary, pointing, and Google Translate, you can usually communicate just fine.

My first visit to Tokyo was in 2016 on a 4-day solo trip (YES, FOUR DAYS), where I packed in as much stuff as I possibly could. My highlights included the Robot Restaurant (now closed, sadly, but absolutely worth the hype for its ridiculousness), maid, owl, and cat cafes, and having a drink at the New York Bar at the top floor of the Park Hyatt, channeling Bill Murray in Lost in Translation. My second trip to Tokyo was in 2019 with my best friend Molly (not to be confused with my sister Molly). This was a 9-day trip where we managed to make loads of friends, visit 1Oak not once but TWICE (gross), bop around Golden Gai, hit art galleries, and enjoy a chaotic Swallows baseball game.

My third and most recent trip was in Nov 2023 with J.J., my boyfriend. We stayed with my sister and her family in Shibuya. And TBH, the visit felt strangely similar to my visits to Brooklyn. We had breakfast with the kiddos, played with them at home and at parks, and had dinner and read stories with them at night. While the kids were at school, J.J. and I bopped around town and visited some old favorites of mine and some new spots that were on our lists. See highlights below, along with helpful tips on Japan here.

HIGHLIGHTS

Yoyogi Park - Nice park near Meiji Jingu Shrine (also worth visiting). There’s a group of old rockabilly dancers that gather every Sunday afternoon near the clock tower and dance in a circle. Totally bizarre and a great way to spend 15 minutes, staring in awe.

Owl Village Cafe Harajuku - Just down the road from the dancers at Yoyogi Park, you’ll find this cool owl cafe. I don’t know where you land on animal tourism, but this owl cafe has brought me a lot of joy over the years. I’ve moved beyond the “swim with dolphins” animal exploitation but am still really keen on visiting animal cafes when I’m in Tokyo. I have gone to owl, shiba inu, hedgehog, and cat cafes and the owl cafe is the SPOT. J.J. had never seen in owl in person before, so naturally we had to come to this owl cafe in Harajuku. A truly great afternoon - shopping for fun, cutesy stuff in Harajuku and then holding some owls. We were able to do a walk-in but you could also put your name down for a reservation, walk around, and then come back later that day.

Usagi Ramen - I noticed this spot near my sister’s house that always had lines around lunchtime. I popped over on my last day in Tokyo for a final noodle meal. This was certainly not a spot I’d go out of my way for since there are SO many amazing food spots in Tokyo, but if you’re in the area, it’s a solid bet. You go into the store and place your food order at the vending machine at the front. I got the Tan Tan Men - Level 1 spicy (medium). The machine gives you a ticket and then you go outside and wait in line until a seat opens up at the bar. Slightly spicy and 100% heavenly. I still think about this meal on a weekly basis.

Heart's Light Coffee - Again, not necessarily worth going out of your way for since there’s so many great cafes in Tokyo, BUT this is an excellent cafe if you’re in the area. The owner plays vinyl and makes incredible coffee. Just a handful of seats, but a great place to start your morning. They also offer a banana latte, if that’s your thing.

Nakameguro and nearby Daikanyama including T-Site - I love this area near Shibuya for a bit of trendy peace and quiet. You can walk along the Meguro River and pop into cafes (like Sidewalk Stand), restaurants, and little clothing shops. Molly (friend, not sister) and I visited in 2019 and it was POPPIN’ on the weekend, but J.J. and I visited a couple times this trip and it was very quiet with not much open. We had lunch nearby at Afuri (see below recommendation). Daikanyama is nearby and also worth a stroll. You'll find the hip T-Site with its incredible bookstore, Tsutaya, perfect for a couple of hours of browsing.

Afuri Ramen - Afuri is in LA now but still remains a solid spot in Tokyo for a light and quick lunch. They offer affordable, light ramen with a chicken yuzu broth (not the traditional pork broth). Pay at the vending machine near the front then take a seat. They also have gyoza YUM.

Bar Martha - I first visited Bar Martha, an incredible vinyl bar, in 2019 with Molly (friend) and a local bar owner/ trumpet player that we met while bar-hopping around Golden Gai. This spot is incredibly cool. There’s rumors floating around the internet that you can’t laugh out loud or you’ll get kicked out, but after two visits I’ve found the general vibe to be — enjoy the vinyl + don’t be loud/ obnoxious and you’ll be fine. They have great bar snacks and tons of whiskeys.

Park Hyatt - (CLOSED UNTIL OCTOBER 2025) If you're up for a fancy dinner, the New York Bar on the top floor of the Park Hyatt has live jazz and incredible views of the city. “Lost in Translation” was filmed here! J.J. and I were actually able to scratch off a bucket list item of mine by booking a night here. While the rooms haven’t been updated in forever (they are finally doing a renovation as of the time of this writing), they are truly incredible and many of them have views facing Mt. Fuji. I really wanted to stay there so that I could use the epic swimming pool and THAT I DID. See my full Park Hyatt review here.

Reiyukei Shakaden Temple - I am obsessessed with this imposing, Star Wars-esque temple. It’s not for everyone, but I’ve gone twice now and have been absolutely blown away by it both times. The architecture is bizarre, especially with the Tokyo Tower in the background. It’s creepy and weird and cult-y feeling, but also somehow really beautiful. I’ve never seen another person in the hallways. But I’ve gone into the actual temple part both times and seen just one person praying. I tried describing this place to J.J. and he probably thought I was insane, but luckily he agreed to come with me and it clicked for him too. Not for the masses, not for the kiddos. Just a place to poke around in silence and feel like you’re on the DeathStar.

Shimokitazawa - Vintage shopping paradise. We spend an entire afternoon here. We also hit nearby LA-based coffee shop, Menotti’s, and walked around the Tokyo Camii & Diyanet Turkish Culture Center.

I have tons of Google maps I’ve created for Tokyo over the years with my various recommendations for food, nightlife, activities, etc. Reach out if you’d like me to send over! If you’re traveling around Japan, see my other posts for destination ideas.