Tokyo: Ancient Vibes & Alleyway Dives

3-Day Tokyo Itinerary

Day 1: Arrival in Tokyo

  • Arrive in Tokyo and check into the Hilton Tokyo.

  • Go on a guided tour of the city, starting in Asakusa.

  • Visit the Ueno Zoo to see plenty of animals, including a panda.

  • Go on a bar crawl through Shinjuku.

Day 2: Explore the City

  • Go to Shibuya Sky (reserve tickets in advance).

  • Hit up Akihabara for arcades, manga, and street karting.

  • Do the samurai experience for a taste of history.

  • Book a photo tour of Shibuya.

  • Have a gyukatsu dinner.

Day 3: Find Peace & Chaos

  • Escape the hustle of the city by visiting Yoyogi Park and the Meiji Jingu Shrine.

  • Visit Harajuku and Takeshita Street for a look at street fashion and street food.

  • Take a walk through Tsukiji Fish Market.

  • Experience the store that is Don Quijote.

Nightlife (each night)

  • Explore the Omoide Yokocho and Golden Gai alleyways for great food & drinks.

Tokyo is a city that has been on my travel list for a long time. I've always been drawn to the juxtaposed historic and futuristic culture, unbelievable food, and vibrant nightlife.

I always like to get my bearings when I’m in a new city—especially one as massive as Tokyo, so we started our trip with a guided tour. This helped us navigate the train system, which seems daunting at first, but it’s easy enough to understand. Definitely load up a Suica or Pasmo card because you’ll be using public transportation quite a bit.

Our first stop was the Asakusa district, which still has the vibe of old Tokyo being filled with food stalls, shrines, temples, and entertainment. We explored the market, and we were happy we came hungry because there was so much good food.

We tried takoyaki (lightly fried octopus dough balls), and this crazy pineapple bread filled with ice cream. Both were delicious. This area of the city also has one of the more well-known temples, Sensoji. This is definitely a great spot to grab some Instagram-worthy photos (but expect some photo crashers).

After the market, we took a quick train ride to Ueno Zoo, where I was dying to lay eyes on a panda. This zoo is actually the oldest zoo in Japan, dating back to 1882, and it's home to more 3,000 animals from all over the world, including gorillas, tigers, elephants, and polar bears.

We wanted to spend more time here, but we were in a time crunch, so we made a beeline for the pandas. They were just as chill and cool as I expected, lounging around and munching on bamboo. Needless to say, we fell in love.

That night, we did a bar crawl through Shinjuku, which is the place to be for nightlife—its filled with neon lights, shopping centers, clubs, and lounges, all watched over by a giant Godzilla head. That gave us a laugh.

We explored two famous alleyways, Omoide Yokocho and Golden Gai, and bounced around some awesome izakayas (Japanese bars & eateries). Each of the izakayas have their own, unique vibe, so check out a few throughout the night. Many of these places don’t take credit card, so come ready with cash. You may also see “No Foreigner” signs (for various reasons, but often because they don’t have English menus or speakers), but there are plenty of other places for you to check out.

We kicked off day two with a visit to Shibuya Sky, an observation deck on the 47th floor of a skyscraper at Shibuya Crossing. The views were insane – you could see pretty much all of Tokyo from up there (and even Mt. Fuji if you’re lucky). You need to secure a ticket ahead of time—we had a morning slot, but plenty of slots are available ~30 days before your trip.

From there, we hit up Akihabara. This place is paradise for lovers of electronics, video games, arcades, manga and anime. We hit up a bunch of arcades, including Super Potato, which has a huge selection of vintage games. But the highlight was definitely the street karting. We got to dress up as Nintendo characters and drive around the city, Mario-Kart style. While it’s a bit touristy (but we are in fact tourists), it’s such a cool way to see the city. We had a blast! (Just a heads up, you’ll need an international driver's license.)

Later in the day, we did a samurai experience. Again, it was maybe a bit touristy, but we had a good time learning about samurai history and getting to hold a 500-year-old sword. Paul made a better samurai than me, which wasn’t surprising.

We also went to an amusement park, which was a spontaneous decision, but it ended up being a blast. And we couldn't get enough of those photo booths – they're everywhere in Japan, and you have to try them out. On the way back to our hotel, we stopped at a 7/11 (they're seriously amazing in Japan) and tried the famous egg salad sandwich. It didn't disappoint.

That night, we did a photo tour in Shibuya and saw the famous Shibuya scramble crossing. It's pretty wild to see thousands of people crossing the street at the same time. For dinner, we had gyukatsu – breaded steak that you cook on a hot stone. It was delicious.

On our last day, we visited Yoyogi Park and visited the Meiji Jingu Shrine, which was a nice escape from the busyness of the city. From there, it’s a quick walk to Harajuku neighborhood, which is home to Takeshita Street, known for its unique fashion, shopping, and street food (of course). We tried a bunch of different things and loved it all.

Finally, we went to the Tsukiji Fish Market. This place was once the world's largest wholesale seafood market, and you can find all kinds of fresh sushi and seafood there. It's a must-visit for foodies. After that, we went back to our hotel, changed, and explored Shinjuku some more. We also stopped at Don Quijote, a huge 24-hour store that sells everything you can imagine. It's a great place to find souvenirs (or another bag, if you purchased more things than your luggage can hold). Be careful though, the theme song will stick with you the rest of your trip.

General Tips

Get a guide for your first day. It'll help you get oriented and learn the public transportation system.

  • Wear comfortable shoes. You'll be doing a lot of walking.

  • Learn some basic Japanese phrases. Even if you don't speak the language fluently, knowing a few basic phrases will go a long way.

  • Get a Pasmo or Suica card. These prepaid cards make it easy to get around on public transportation. But you’ll still want to carry some cash on you, too, as not everywhere accepts cards.

  • Don't be afraid to try new things. Tokyo has so much to offer, so step outside your comfort zone. There is a different Tokyo experience for everyone, so find what works for you.

Where I Stayed