My Japan Itinerary – Damsel In Dior


My first ever trip to Japan was a total whirlwind that was filled with a packed itinerary, lots of laughs and such an amazing experience.

My mind and heart are still fluttering over the quick 9 day trip! I could have used more time, but I still feel like we covered so much with the time we had.

Below you will find a full break down of each day and what we did, where we ate, and where we shopped.

For a full breakdown of everything I packed and wore, head over to this post from my Basic substack newsletter. 


Night One:

Masa Ishibashi – Thanks to jet-lag, we nearly fell asleep at the table but it was a great first night spot. It’s a great area to walk around before dinner and shop hop. We popped in Dover Street and had a pre-dinner cocktail at Ginza which was a super hip record playing bar. Most restaurants and bars are up in office buildings so expect that.

Day – Night Two:

We hit the ground walking and started at the famous Shibuya Crossing. It’s cool to see but not a must. Stumbled across so many interesting and unique moments like a Farmers Market at UNU. We walked and walked to Amore Vintage Aoyama – great vintage Hermes selection and lots of locations . . . and then to Casanova Vintage – another amazing vintage shop! Next we walked through Tokyo Plaza and saw the mirrored escalators which was cool. Then off to Meiji Shrine where we made wishes and saw the beautiful shrine. From there our legs were burning so we took a quick cab to YoYoGi Park to take in the Cherry Blossom trees with our Australian friends and wine. That was really cool because it was a tradition that the Japanese have been doing for over 800 years. Truly special!

Pre-Dinner drinks at Park Hyatt New York Bar (the hotel we stayed at) which was amazing and surreal. Lost in Translation is a favorite movie of mine so this was a “moment” for me.

For Night two we had a really fun, quick and easy dinner at Daian which had great Soba and was in a fun area for playing with gaming shops. read more here

Day – Night Three:

We spent most of the day in Daikanyama walking around the shops. Specifically loved Hedy for vintage. Cabbed (a long cab) to Sakura Bashi Bridge which was my favorite Cherry Blossom viewing point with locals. We were the only tourists there!

We started the night off at Team Labs which was a really fun art experience that I recommend if you have time. Cruised back over the bridge (beautiful) for happy hour at The Edition (fun) and had dinner at Sushi Yuu. This was my favorite dinner in Tokyo. We ended the night at Karakoke Kan in Shibuya which is where Lost in Translation filmed (seeing a theme?) We ended at the Golden Guy mini bars.

The Golden Gai is an area in Shinjuku, Tokyo, with around 200 bars in a small area of alleyways. Most of the bars are so tiny – some with as few as 6 seats! They really are like walk-in cupboards, with just the bar and a space in front.

Day – Night Four:

Went to Takeshita Street for some souvenirs for the kids and ended up at Tomorrowland and a sake taking at a random shop. You can talk and eat street food for days in this city. Our final dinner was at the French Michellin star Equisse but I think we were too jet-lag sleepy to truly enjoy it.


Day Five – Day 6:

Trained all day to the James Turrell House of Light. To say that this experience was once in a lifetime, never forget places I’ve visited is a huge understatment. What an amazing journey. I warn you that it is most definitely not for the faint of heart. You spent a LOT of time getting to the House of Light and upon arrival you will definitely have one of those “where the hell are we” moments. You bring your own food, etc. and camp out on mats on the floor. But there’s cell phone service, heater/AC, towels etc. and the best art exhibits I have seen in my life. The house books out well in advance. We had 5 people but booked it for 6 people because otherwise you will be sharing the space with fellow travelers if that’s your jam. Also, we booked it for two nights so we could have a later check out time because they’re pretty strict! See more here. We stayed here one night and then trained our way to Kyoto.


Night 6:

Checked into the Hotel Mitsui and what a dream it was. I 100% recommend this hotel if you’re in Kyoto. Absolutely stunning and has everything you want head to toe!

Took our swaying train legs to a tofu driven restaurant called Tousuiro Kiyamachi Main Shop. If Tofu is your thing, then this place was phenomenal. Tofu is not my “thing.” We walked around town a bit and popped by BAL which is a really great multi-level shopping mall that has a few brands unique to Japan.

Day – Night 7:

Took the 40 min train trek to see the deers. It’s a super popular destination called Nara Park and it really is special. There’s a magic here and so many damn deers. You will be laughing and in awe. They’re like 1,000s of house cats. Apparently they were placed there to guard the temples but now it just seems like they’re there for the biscuits and pets.

After that we walked around town and stumbled upon the cutest LL Bean but more elevated canvas bag store called Ichizawa Shinzaburo Hanpu which I later found out has been making these high quality bags for over 100 years and are sold only in Kyoto (score!). We went back to the hotel and walked to Brown Kyoto which is a vintage shop Amber Lewis suggested because it’s so close to the hotel but it was closed. We ended up popping in to the cutest sake shop just right next door for some tasting and shopping called Sake Cube Kyoto which I highly suggest. You could hit both up at once.

We saved some energy and stomach space for one of the most amazing dinners I’ve ever had in my life. Monk. Need I say more? Yoshihiro Imai’s 14-seat, seasonally inspired restaurant, set on the cherry blossom-lined Philosopher’s Path in Kyoto. I suggest googling more on it and/or watch the Chef’s Table episode all about it. It’s impossible to get in but luckily we had Ariel pull some strings for her special birthday dinner. It was an unforgettable night.

Day – Night 8:

We went to the Fushimi Inari Shrine temple and I wish I’d worn sneakers. You can just pop in for the beginning but of course I wanted to go to the top. There are drink, bar and food stations all along the way and I suggest making a long morning out of the experience. At the bottom there are the most amazing food trucks for lunch but we had a really amazing lunch reservation.

We intended to see Bamboo Forrest after our amazing lunch. We had a reservation at Tempura Matsu which was my second favorite (behind Monk) meal of the trip. It was very authentic and felt so special. It’s also very close to bamboo forrest so you can kill both birds with one stone. Sadly this is when I started to fall ill.

I didn’t post on Instagram but after this lunch I headed back to the hotel and fell into a dark hole. I guess my back to back travels from New York, to Cabo, to Toko, to Kyoto just all caught up with me and I caught strep throat. Damn. I really only missed out on the last night because we made our way back to Tokyo on Day 9. We had planned on staying at the new Janu in Tokyo for one night but instead, I caught an early bird home (masked up) and went straight to urgent care and home to rest up to see my babies.

Outside of my little strep throat souvenir, this trip was a true bucket list that I was so thankful to finally check off my list. I will absolutely be going back one day and would very much like to spend more time in Kyoto and perhaps visit Osaka. Have you been?

I hope you enjoyed this itinerary and find it helpful! There are so many amazing places to see, you really can’t go wrong!

I simply must thank Case and Ariel, our fearless leaders who made every reservation and guided us. They’d been before and had the best laid plans. We had an absolute blast!

xoxo jacey


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