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Tokyo: How to Take The Life Changing Trip You’ve Always Heard Dreamed Of

This is the Tokyo Travel Guide for people who expect only the best.

Aside from the mind-melting robot shows and the Harajuku girls style, the work-ethic and desire for excellence are what made a lasting impact for me on my 5 night trip to Tokyo.

During my trip through Tokyo, I thoroughly researched the best shopping, dining, and drinking all from the perspective of a jaded New Yorker who is constantly getting bombarded with the “best bar, restaurant, cronut,” in the World.

toyko travel guide

Below are my recommendations for truly amazing experiences in Tokyo that you can’t find on Zagat (because they don’t use it) nor on any typical guide book.

Why Should I Even Visit Tokyo, I’ve Seen Asia…

But first, maybe you need some convincing. I know Tokyo wasn’t the first on my list prior to visiting.

I have been to Asian before: Hong Kong, Bangkok, Phuket, Khao Lak, Ko Yao Noi, Singapore. I thought I had seen enough of Asia to get a feel for how things are, but boy was I missing out.

You Should Visit Tokyo Because, Quite Frankly, You Can’t Experience What The City Is, Anywhere Else in the World


The city is insanely clean; streets are almost sticky from the fresh asphalt; not a pothole is in sight, nor a piece of garbage

tokyo travel guide to food

No matter what restaurant you go to, the chefs will be extremely precise with how they prepare and serve your food. They hand you a glass or a plate with both hands (which seems like a small thing, but think about this the next time you’re eating anywhere else in the world.

tokyo travel guide bars

Despite the city having a relatively humdrum reputation, there is an excellent drinking culture, and plenty of places to drink a bespoke tipple or get sloppy at 24 hour dives.

When you walk into a store, the shoppers will welcome you with a 10 phrased welcome, and when you buy something, you won’t get a simple “thank you”, but rather a phrase that is continued long after you’ve said your own “thank you”, and have already turned around to walk out of the store.

I’ve been all around the world, to many parts of Asia, and never had such an amazing time as I did in Tokyo.

To me, I always know it’s a great place when, on the second or third day, I’m already planning my return trip.

7 weird things to do in Tokyo

  • Visit a Maid cafe: it’s where love for fetish and cosplay meet. Waitresses prance around in maid costumes and play personal servant to patrons as though they were in a private home.
  • Eat at Robot restaurant: Robot Restaurant is best described as a loud, colorful cabaret show that stretches your senses to their absolute limit. Starring scantily clad majorettes, an army of dancing 8-foot tall robots, and a soundtrack packed with hits from Broadway musicals.
  • Check out the fashions in Harajuku and Akihibara: People-watching gets a whole new meaning in neighborhoods of Harajuku and Akihibara, where enthusiastic fashionistas and cosplayers parade their finest get-ups on the city streets.
  • Shake to Dancehall Reggae Music at Garam: You wouldn’t expect reggae music in Tokyo, but it’s actually widely represented.  Garam in Shinjuku-ku is one of the many reggae nightclubs springing up around Tokyo.
  • Auction for Tuna at the Tsukiji Fish Market: The Tsukiji Fish Market, one of the world’s largest fish markets, holds a 5 a.m. sell-off which is a one-of-a-kind event. It features lots of fish tossing and loud, rapid-fire Japanese from auctioneers and bidders alike.
  • Walk through Shibuya Crossing: Tokyo’s most famous intersection is more wonderful than weird. For the best view, get a window seat at near Starbucks.
  • Sleep at a Capsule Hotel: Experience one of Japan’s most unique sleeping situations and stay at Green Plaza Shinjuku and many hotels alike.

You Should Visit Tokyo September-November for The Best Weather

So let’s start from the beginning. Our trip to Tokyo was in May, which is the start of rainy season, which we didn’t experience much rain, but was not the ideal month to travel.


The best time to go to Tokyo is September – November. Temperatures will be very moderate with highs of 70s and lows of 60s.

April-May is Cherry Blossom Season in Tokyo

If you want to save money, visit Tokyo in the non-peak season, late April/early May, which would put highs in the lower 70s and lows in the 50s, but with a chance of rain.

This is also cherry blossom season, and as they say, April showers bring May flowers.

If You Want to Fit In, You Must Learn These Japanese Etiquette Rules: They Actually Require Them

This is what you need to know before you touch down in Tokyo.

  • Etiquette is a must: when riding escalators stand on the left, don’t cut to the front of a queue and be mindful about where you smoke in public.
  • Table manners: don’t point chopstick tips at anyone, never leave them planted vertically in your rice and never use them to pass food to someone else.
  • At home: It’s customary to remove your shoes when entering somone’s home. Make sure your socks don’t have any holes.
  • When paying: don’t hand money to the cashier, you will only be asked to place it in the tray. Don’t worry about tipping either, it’s not part of the culture.
  • Hailing the cab: Tokyo’s taxis are very tidy and drivers are courteous. They even open and close the back door for you (from their seat) so don’t try to slam it shut or even open it.
  • Cleanliness is King: to the Japanese people, being clean is extremely important. In grade school, kids are taught how to clean, and are actually in charge of cleaning their own classrooms. there are also no trash cans anywhere in site on the streets, yet everything is spotless. Japanese people are taught to take their trash with them and throw it away at home or at a store, never on the street.
  • Bring your own soap & towel: in public restrooms there are often no paper towels, also for cleanliness, so make sure to grab a handkerchief to bring along with you to wipe your hands.
  • Smoking or Non? Tokyo does not ban cigarettes in restaurants and bars, which caught us off guard a couple of times while we were enjoying our meal. if we could change one thing about Tokyo, it would be to ban cigarettes in restaurants/bars.

Converting USD to Yen is a breeze. It’s basically $1 is $100 Yen, so if you see a price that’s 6,500 Yen, you just cover the last 2 zeros with your finger, and know it’s $65.

Prices in Japan are about 10-15% more expensive than New York, and are going to be a lot more expensive than non-major cities in the US.

Tokyo Neighborhood Guide and Summary

A mere five minutes from Tokyo Station takes you to this lively neighborhood, an epicenter of otaku, a virtual playground for anime and manga fanatics. It’s great for discovering the subcultures and Tokyo’s nightlife.

Immerse yourself in Akihabara's virtual reality, Tokyo's audaciously animated electronics center.

Immerse yourself in Akihabara’s virtual reality, Tokyo’s audaciously animated electronics center.

Harajuku reigns as Japan’s forward-thinking fashion capital and is the place to see and be seen. Its alleyways are like a huge catwalk that pop with polka-dots, plaid skirts, and neon high tops. You’ll want to visit Harajuku for shopping and street style.

If you want to see what's hip, take trip to Harajuku.

If you want to see what’s hip, take trip to Harajuku.

This neighborhood is Tokyo’s rising star of creative bohemian acclaim. Shimokitazawa shares Harajuku’s highly stylized aesthetic, but it’s slightly removed from the masses that gather in the center of the city. Visit is a must if you’re looking for great wining and dining.

tokyo shopping guide

Shimokitazawa really reminded me of the warehouses of Williamsburg and Bushwick, Brooklyn

Find bars inside actual living rooms in what may be Tokyo's trendiest, and friendliest, bohemian scene.

Find bars inside actual living rooms in what may be Tokyo’s trendiest, and friendliest, bohemian scene.

Nestled within Meguro District, Nakameguro exudes a laid-back attitude of the kind where shoppers browse without the pressure to buy and tables linger without the pressure to pay the bill. Here you can leaf through art books suited for the coffee table or buy a vintage suit from a man in a van.

A different way of shopping in Nakameguro.

A different way of shopping in Nakameguro.

By day, hautely dressed denizens flood out of the station and into Shibuya’s top department stores, trendy boutiques, and nearly-too-cool izakayas. By night, Shibuya’s sidewalks swell with chattering youth and the sounds of DJs spinning in suspended glass booths. This neighborhood never sleeps.

The masses crisscross Shibuya's maze of streets, alleyways, and central intersection at a dizzying pace.

The masses crisscross Shibuya’s maze of streets, alleyways, and central intersection at a dizzying pace.

Tokyo travel guide shopping

Down the street from Shibuya crossing was a quaint French coffee shop perfect for people watching

tokyo shopping guide

Aoyama, just outside of Shibuya, had awesome specialty shops. This is where I found Freeman’s the offshoot of the SOHO menswear brand

Upscale, poised, and stylishly coiffed, this central Tokyo area’s winding streets, open-air cafes, art spaces, and salons lend it a distinctly European ambiance. Ebisu and Daikanyama are collected and chic, perfect for watching the sidewalk.

Collected and chic, Ebisu and Daikanyama exude classic style and high-end comfort.

Collected and chic, Ebisu and Daikanyama exude classic style and high-end comfort.

Best Hotels in Tokyo, Where to Stay

Andaz Tokyo
Andaz Tokyo Toranomon Hills is located in prestigious Toranomon, a key business district of central Tokyo.

It has 164 rooms, including 8 suites, featuring spacious guestrooms with Japanese-inspired style designed by  Tony Chi and Shinichiro Ogata.

andraz tokyo

tokyo andaz review

The mini bars at Andaz Tokyo were a work of art. Each of the snacks had their own compartment, and the mini bar was stocked with an excellent bottle of Japanese whisky

tokyo best hotels

The suite at the Andaz Tokyo

View from the Andaz tokyo rooftop bar

View from the Andaz tokyo rooftop bar

Andaz Tokyo rooftop bar

The Andaz Tokyo rooftop is also available for weddings and corporate events.


The Andaz Tokyo rooftop bar with stunning views and craft cocktails

The hotel features a breathtaking Rooftop Bar on the 52nd floor with open-air seating, city’s highest stand-alone chapel 8,300 square feet of flexible event space, 5 treatment rooms, a unique 20-metre pool overlooks the Imperial Palac and latest gym equipment.

Park Hyatt Tokyo
Park Hyatt Tokyo is a true “over-the-top” experience. Perched on the top floors of a modern skyscraper that towers above one of Asia’s most thrilling cities, this hotel is widely acknowledged to be Tokyo’s finest.

It has 177 generously sized guest rooms, including 23 suites, seven treatment rooms, whirlpools, wet and dry saunas, cold plunge pools,
fully equipped gymnasium, indoor swimming pool, a library, a wide range of restaurants & bars, a pastry boutique and many more.

tokyo travel guide lost in translation

Park Hyatt was where Lost in Translation was filmed

If this hotel look familiar to you, it’s because you’ve already seen it in a hit movie Lost in Translation.



Grand City View apartment Shibuya
Recently renovated, this is a truly gorgeous and spacious 112 square meter apartment. From the big window in the living room, you can overview the whole city.

Book here.

Grand City View apartment Shibuya

EBISU 7BR+spacious LR next to Shibuya-Roppongi
This huge seven bedroom apartment is perfect for a trip with all your mates. It features a terrace and all the amenities you can imagine and it’s suitable for parties as well. Hangover Tokyo edition?

Book here.

EBISU 7BR+spacious LR next to Shibuya-Roppongi

This is a flat with superb Shinjuku city view with Tokyo tower, it’s decorated in modern Western condominium style with a kitchen bar,
two semi-double beds, one double bed and a futon. It’s a truly a perfect place for high-end Shinjuku experience.

Book here.


Where to Eat in Tokyo

Japanese food falls into one of these main categories:

  • Tempura: fried vegetables, meat and fish
  • Tonkatsu: deep-fried breaded pork
  • Ramen: tonkotsu being the pork-based ramen
  • Sushi: rice with raw seafood/vegetables on top
  • Don: rice bowl with various raw/cooked seafood & vegetables

These are the best restaurants in each category

Best Tonkatsu in Tokyo

Maisen Shibuya Hikarie
Great ambiance and great food! The menu is traditional Japanese with fresh seasonal ingredients and the best part is your meal comes with free cabbage and rice refill.

2-21-1 Shibuya | Shibuya Hikarie 6F, Shibuya


Maisen Aoyama Honten
This is one of the most popular restaurants in the area and the tonkatsu is said to be one of the best ever tasted. The staff is really friendly and the 70s decor is a true charm.

4-8-5 Jingumae, Shibuya 150-0001, Tokyo

Tonkatsu Maisen Aoyama Honten

Best Ramen in Tokyo

Ichiran, Shibuya
For Tonkotsu-based ramen visit Ichiran in Shibuya, which is a vending machine with one of the best ramen, told by the locals. You eat the noodles at a small cubicle, so it’s perfect if you just want to grab something on the go.

1-22-7 Jinnan | Iwamoto Bldg. B1F, Shibuya 150-004 Tokyo


This place offers regular salt based ramen, which is tasty and fast served. You need to select and pay your meal in advance through machine and you can enjoy your food in authentic conditions.

1-1-7 Ebisu | 117 Bldg.1F, Shibuya 150-0013, Tokyo


Best Sushi in Tokyo

Sushi Bar Yasuda
One thing we learned from Chef Yasuda is sushi is all about the rice. It should be tightly packed, have a flavor of vinegar, and taste absolutely amazing.

4 chome 2-6 Minamiaoyama Bldg 426, B1, Minato-ku, Tokyo



The best sushi don is going to be found closest to the fish market, where it’s going to be the freshest. Prepared for you only a couple hours prior to being fished from the sea.

Sushi Zanmai
Located at the Tsukiji Market, this sushi will melt in your mouth. There’s usually a cue but it’s all worth it when you try the freshest sushi in town.

3-11-9 Tsukiji | Tsukiji Square bldg1F, Chuo 104-0045 Tokyo

Sushi Zanmai

Best Restaurant in Japan that doesn’t fall under these categories

Down the Stairs by Arts & Science
This is a cool concept store where you can dine and shop in beautiful space with a laid-back atmosphere.

6-1-6 Minami Aoyama | Aoyama Palace 110, Minato


If you must eat pizza in Japan, …like we did, go here:

Pizzeria e trattoria da ISA
The pizza was very good, not as good as Roberta’s, Joe’s Pizza or Juliana’s Pizza but definitely filled a void while traveling through Asia for 14 days.

1-28-9 Aobadai | Meguro 153-0042, Tokyo


Best Bars in Tokyo

Old Imperial Bar
Definitely worth visiting this great old bar to capture a bit of the days gone past. Good selection of whiskeys and great atmosphere.

1-1-1 Uchisaiwaicho | 2F Main Bldg., Imperial Hotel

best bars tokyo

Bar Trench
rated one of the 50 best bars in Asia, this one sure deserves your visit. Many of the drinks in the menu came with some form of “drama” – be it the way it’s presented or the way it’s being done.

1-5-8 Ebisu Nishi | 1F, Shibuya 150-0021, Tokyo

bar trench

Golden Gai
This is a 5-6 block radius of over 100 bars, some as small as 4 seats. It’s the ultimate dive-bar destination for people thirsty for sake and Japanese beer, as well as shops specializing in every different type of spirit.


Sakeria SakeBozu
Great place if you want to experience fine Japanese wining and dining.

1-37-1 Tomigaya | Lona YS Bldg, Shibuya 151-0063


How to Shop in Tokyo

One of the biggest differences between Tokyo and the states is that their retail goes vertical.

It’s very unheard of in New York for a retail store to be on the 3rd floor, but in Japan, where space is tight and zoning seemingly arbitrary, we visited a retail vintage shop on the 5th floor of a residential/commercial low-rise in Shibuya. We actually had a maintenance man lead us to the store.

Best Menswear Shopping in Tokyo

Ron Herman
A menswear boutique that offers great shopping experience and clothing that is made with thought about the one who will wear it.

9−7−4, D-B113, Tokyo Midtown, Minato, Tokyo 107-0052
ron herman2

Brand Collect
This is a vintage/upcycled store for luxury men’s brands. There was a bomb Givenchy leather bomber hoodie for 50% off, amongst other great brands like Balmain, Saint Laurent, and Commes des Garcons.

1-8-5, マロンビル, Shibuya, Tokyo 150-0001

brand collect

Best Vintage Shops in Tokyo

Vintage Paris
Awesome place for vintage Chanel purses, brooches, clothes, and accessories. Must visit for all who love the French style.

107-0062 Tokyo, Minato, Minamiaoyama, 7 Chome−10−3
vintage paris

For second-hand clothing visit Kinji. They have a great selection of just about anything you might be interested in, from band t-shirts to baby-doll clothes that you see in Harajuku.

31-, MILKFED, 4 Chome Jingumae, Shibuya, Tokyo 150-0001

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