Japan is more popular than ever thanks to the re-opening of its borders in 2022 and a weak yen, in addition to already being one of the most popular tourist destinations in the world. For me personally, I’ve been once before but felt like I had only scratched the surface of the three cities I went to, so I was dying to go back and find new experiences.

For those going with a large group, this itinerary should hopefully help you plan a trip with family/friends that strikes a good balance of having a lot of ground to cover while not bouncing on trains the whole day. Planning a group trip for 6+ in Japan will prove to be a daunting task for you as there are many places that can’t take large groups, but when possible, dividing the group will make your plans much more manageable.

When planning any trip, using Google Maps to get a general idea of the area and planning how to reduce travel time will be absolutely essential. When I first went to Japan, we found ourselves using the metro often to bounce back and forth between things we wanted to do, and while the metro is a very convenient way to get around, planning to spend more time in one area will be a much less hectic and more enjoyable travel experience for you. In general, I planned one or two big things to do in a day, then organized travel/dining to get from the hotel to that area without going back and forth.

While this could be a great first-time trip itinerary for Japan, as it does have the big 3 cities of Tokyo, Kyoto, and Osaka, there were still a lot of first-time experiences we simply didn’t find time for, and I recommend using both the itinerary and the notes section to find what works best for your group.

1. Highlights
   1. Tokyo
   2. Kyoto
   3. Osaka
2. Itinerary for Tokyo, Kyoto, Osaka – 9 Days
   1. Suggested Order to Booking
   2. Days 1 – 3
   3. Day 4 – 7
   4. Day 7 – 9
   5. Extra Notes:

Highlights

Tokyo

Tokyo needs no introduction, so as the largest city in the world, it’s no surprise that almost 3 million tourists visited Japan in 2023. As part of that throng of tourists, we spent three days trying to hit as much of our list as possible, but as most of the group had visited Tokyo before, we tried to stay away from a first-timers itinerary. With nearly infinite activities for every proclivity, you’ll be able to find something that fits your interest. We still did a lot of insanely popular things like going to the newly opened Shibuya Sky observation deck or visiting Senso-ji, but also went to places like Ginza6 and Teamlabs Planets, which might not fit in everyone’s first times three – day trips to Tokyo. 

Shibuya Sky – Featuring 360-degree views of Tokyo, Shibuya Sky has the comprehensive viewpoint of the city, and I’d highly recommend spending the ~$15 cost of admission. Sweeping views of major landmarks, including Shinjuku Gyoen National Garden and Tokyo Tower make this one of the best ways to get those scenic shots that you want.

Teamlabs Planets – For those into art and culture, Teamlabs Planets is a great representation of a modern art exhibit in Japan. Engaging multiple senses, this art exhibit combines digital and physical elements centered around ‘water’ and ‘garden’ themes. Highly recommended, but there’s also a newly opened Teamlabs Borderless that also seems visually stunning.

Seso-ji and street food – On the flip side of art and culture in Japan is Senso-ji, a temple/market in Asakusa that showcases the food, worship, and markets of traditional Japan. It’s a tourist attraction, sure. Maybe not 100% authentic, sure. But the food was good, and the sights were nice, so it’s definitely worth it.

Kaitenzushi – One of the biggest surprises of this trip to Tokyo was how damn good kaitenzushi (conveyer belt sushi) was. Incredibly easy to order, cheap, fresh, and varied sushi on this scale is something that I have never found outside of Japan.

Omakase – And because there’s something for everyone, on the flip-side, we went to an 8-seat, 3-hour private omakase sushi dinner that same day, booked through a site called Pocket Concierge (which has various fine-dining options in English that you can pre-pay for). Incredible sushi and sake in Roppongi made me feel like a king. The price was around $200, which was well worth it for the step up in quality (and copious amount of sake consumed).

Kyoto

Arashiyama – Large area west side of Kyoto that has great proximity to the famous Kinkaku-ji (Gold Temple), Arashiyama bamboo forest, monkey park, and a bevy of shopping and dining. This area really embraces the traditional aspect of Japanese culture, and is a great place to find souvenirs, tranquil spaces, and a glimpse into the past. (also cheap beer and yakitori)

Gin Bar – I Wish I spent more time here, but my friends found a gin bar underneath Kyoto Tower that specialized in gin cocktails that has inspired many of my own cocktail creations since. They also had a huge leg of serrano ham that I regret not having.

Kaji Kyoto – Probably the culinary highlight of our trip (yes even over omakase sushi). Kaji is the brainchild of popular Hawaii restauranteur Chris Kajioka, who decided to start a venture in Kyoto. Featuring a blend of seasonal Japanese, Peruvian, and Hawaiian, this pre-fixe meal featured amazing flavors, good wine pairings, and great people.

Suntory Yamazaki Distillery Tour – Japanese whiskey has exploded in popularity recently, and Suntory’s Yamazaki is at the forefront of this movement. Only available by lottery, we were fortunate enough to win the opportunity to tour the distillery and get a behind-the-scenes look at how Yamazaki produces its world-famous whiskey. Complete with an interesting whiskey tasting at the end, where we sampled the whiskey at various stages of maturation, something that I’ve never done before.

Osaka

St. Regis Hotel Bar – An upscale bar in an upscale hotel, the St. Regis Hotel Bar exudes opulence – and serves it too. The cocktails here have a sublime balance of flavors and were all extremely interesting. Also had a mind-blowing omakase cocktail from the bartender Yukari, which I think about once a week.

Bar hopping around Kuromon Ichiba Market – Osaka is known for its izakaya/drinking culture, and it did not disappoint. Unfortunately do not remember and did not record much of this night, which is kind of a testament in itself.

Dotonbori – Dotonbori is Osaka’s most popular area, filled to the brim with piping hot takoyaki, small izakayas, and loads of shopping and dining options. I wish I spent more time here, finding small bars and hidden gems on both sides of the Tombori River.

Itinerary for Tokyo, Kyoto, Osaka – 9 Days

Suggested Order to Booking

1. Flights
2. Accommodations
3. Restaurants 
4. Tour/Park/Tickets/Shinkansen to Kyoto and Osaka

Days 1 – 3

Staying: Hotel Rose Garden Shinjuku 

Day 1
Doing:
Immigration/transit/hotel check-in (~3-4 hrs)
Chill/eat – Kabukicho Tower

Day 2
Doing:
Shinjuku/Shibuya:
Shinjuku Gyoen National Park
Shibuya Sky 
Yoyogi Park
Meiji Jingu
Loft
BEAMS
Shinjuku Southern Terrace
Harajuku
Shops
Crepes
Omote-Sando 
Bape
Shibuya Crossing/Miyashita Park (KitKat Chocolatory/more shops)

Minato:
Odaiba: Gundam/Toyosu Market
Team Labs We went to Planets, but they have since opened another exhibition in Azabudai Hills called Team Labs Borderless)
Tsukiji Market
Tokyo Tower
Roppongi
Shinjuku Batting Cage/ Another one
Kabukicho/Omoide Yokocho
Karaoke

Day 3
Doing:
Asakusa – https://www.youtube.com/watch?v=KoeLEj7TV4I 
Senso-oji Temple
Asahi Sky Room Bar
Pelican Cafe
HATCOFFEE
Street food
Tokyo Skytree shopping

Akihabara:
Yodobashi Camera/Janpara 
Animate
Animal Cafe – Monta Cat Cafe

Ginza:
Tsukiji Fish Market
Grand Seiko
Itōya Stationary Store
Ginza Mitsukoshi
G Six
– Shooting Center
– JWC Whiskey
– Yurakucho
Bongen Coffee
Dinner at Roppongi Taida (Booked with Pocket Concierge)

Day 4 – 7

Staying: Sanjusangendo Yoinotake 

Day 4
Doing:
Depart Tokyo via Tokyo Station: ~3 hours 
Kyoto Station – Icoca card
Kyoto Tower Gin Bar –
Katsukara – Katsu
Bag Drop Off
Nishiki Market
Kishi Kishi Market

Day 5
Doing:
Early morning – Fushimi Inari Taisha

Arashiyama and Sagano:
Monkey park
Tenryuji Temple
Ebisuya (Bamboo Forest path)
Kinkaku-ji
Gion/Kiyomizudera
Kimono Rental
Kimono Rental Guide/Options
Kaji

Day 6
Doing:
Suntory Yamazaki Sake Distillery 
OR day trip to: Nara / Amanohashidate / Hozugawa River Boat Ride (2 hours)
Sake tour
Maccha House
Nishiki Market

Day 7 – 9

Staying:
Namba Airbnb 

Day 7
Doing:
Leave Kyoto: Arrive ~20min
Osaka Station/Umeda
Osaka Castle
Dotonbori
Round 1 Stadium
Shinsaibashi (shopping/food)
Kuromon Ichiba Market (covered market with produce/street food) 
Shinsekai (Osaka food and entertainment) 
kushikatsu

Day 8 

Doing:
Universal Osaka (IF it’s your first time in Osaka, I would recommend skipping this and supplementing with things you missed on the previous day)
teamLab Botanical Garden opens 7 

Day 9
Doing:
Katsuo-ji (Temple north of Osaka)
Namba Parks
Namba Yasaka
Massage (There’s quite a few options around Namba Station)
Check-out and store luggage at Namba Station
Food/Shopping/Leaving
Karaoke

——————————

Extra Notes:

https://www.japan-guide.com/railpass/ (Not worth it for our two rides)
https://www.japan-guide.com/news/japan-rail-pass-cost-increase.html
Osaka to Kyoto
Where to buy / Smartex
Online:
Tokyo to Kyoto 
Kyoto to Osaka 
Pocket Wifi
https://www.japan-guide.com/railpass/Ichiran-Ramen 
Sake Distillery Tours in Japan