For all its high rises and striking towers, the throngs braiding their way through train stations and across intersections, it’s still easy to spot old Tokyo amid all the new. As I rode between Narita airport to downtown Tokyo, I was startled to see neighborhoods with traditional tiled roof-lines and green fields. A few seconds later I faced rows of apartment buildings lined up like soldiers along the route. Tokyo never fails to fascinate, and this third visit was no exception. While there are hundreds of suggestions about what to see in the vast city, if you’re looking to create a unique Tokyo Itinerary, focus on the contrasts and consider these suggestions.

*** This post includes affiliate links but as always suggestions and opinions are my own.***

Consider putting bicycling on your Tokyo Itinerary

Getting Around – From bullet trains to bicycles

When you first arrive in Tokyo adrenaline kicks in and wakes you up after long flights. However getting to your destination takes focus and while there are information booths in the airport, have a loose plan in place before you head out. You’ll find bus shuttles and limousines to get from the airports to Tokyo’s center. I’ve always arrived via Narita, which has more international flights than Haneda, which is closer to Tokyo.

It’s a bit daunting to take several trains into town but not impossible. Riding the trains has gotten easier over the years with multilingual announcements and signage. When I had a local friend to guide me, my greatest task was figuring out where to look first. You’ll have to save the Shinkansen high speed trains for travel outside of Tokyo but if you have a JR Pass, which includes reserved seats on the bullet trains, it will come in handy for certain lines in the city.  Pundits suggest that the best way to get between Narita and Tokyo is the JR Narita Express.

Pedal Around Tokyo!

Tokyo locals take trains often of course but have always gotten around easily by bicycle. There’s just not room for everyone to own a car and those that do pay premium for parking, when it can be found. I wish my itinerary had left time for a bicycle tour like one from Viator:


Old Tokyo Architecture and the New

Old Tokyo is actually hard to avoid even in the midst of all the new buildings. The most famous architectural wonder is the Imperial Palace with its surrounding moat. The gardens are a perfect refuge if you’ve been walking the streets all day. Fortify your senses there no matter what season and if possible, attend an event inside the grounds.

Enter the Ginza district's exclusive Bar High Five

Enter the Ginza district’s exclusive Bar High Five

Just a few long blocks away is the Ginza district, an electrified network of designer shops as well as affordable emporiums like Uniqlo, which has stores in strategic American cities as well. The district is a marvel anytime of day.

The popularity of the Rappongi neighborhood is apparent as soon as you exit the train station. There are glitzy restaurants and gleaming storefronts but some of the most spectacular reasons rise far above your head. Inside the Mori Tower, the rooftop museum has one of the best views of the city (find out more about the tallest views in Tokyo in this earlier post.) Rotating exhibits and several restaurants are included but stay to watch the sunset and admire the Tokyo Tower waking up in the distance.

Japan's largest cemetery near the Nippori Train Station

Japan’s largest cemetery near the Nippori Train Station

Tokyo’s past quietly astounds in the quaint neighborhoods of Ueno and Tanaka. Just a few steps from the Nippori Station you walk through an ancient cemetery with 7,000 graves. This is Japan’s largest cemetery and it spreads over 25 acres between the station and the narrow streets of Tanka. The cemetery was once part of the Tennoji Temple. Village shops and cafes have been run by families for generations and when a new endeavor opens, it often works around and inside the old buildings. See more about eating and drinking here in the food section below.

Diversions in Old Tokyo and New

As of this writing, the 2020 Olympic event spaces are being polished and completed. The triathlon, marathon swimming and beach volleyball competitions will take place on Obaidba island. The island has been completely rebuilt since the 1800’s when fortresses protected Edo from attack by sea. You can still glimpse the overgrown No. 6 Battery from the Rainbow Bridge. Since the 1990’s Obaidba Island has developed a theme park atmosphere in Palette Town with event spaces and the Dikanransha Ferris Wheel looms over it all.

The big wheel on Obaidba island

The big wheel on Obaidba island

Long before the Olympics were flourishing internationally the art of Sumo wrestling was popular across Japan. In Tokyo the district of Ryogoku, remains the center of all things Sumo. The current Sumo stadium was built in 1985. There are Sumo stables where wrestlers live and train. Of course, they need to eat – a lot. Restaurants in the area serve Chanko nabe, the staple food of sumo wrestlers. The hot pot dish is filled with vegetables, seafood and meat in many variations. Some of the owners are retired Sumo wrestlers as well.

The Imperial Palace moat with Ginza towers beyond

The Imperial Palace moat with Ginza towers beyond

Classic drinks and new

One of the most Japanese of experiences is to visit a fish market. Tsujiki (see it in this much earlier post) was world famous and filled the waterfront close to the Ginza district for centuries. It took decades to find and negotiate the building of the new Fish Market of Toyosu. Now visitors are welcome to watch the daily auctions from wide viewing platforms above the action. *See the tour link above.

Coffee pod culture in the rooftop Mori Museum cafe.

Coffee pod culture in the rooftop Mori Museum cafe.

While you can sip Japanese whiskey at bars throughout the city, the Bar High Five in the Ginza is a distilled drinker’s dream. Once you locate the basement space and pay the entrance fee, you’ll slip into a slim, dark space. Bill Murray’s character in the movie Lost in Translation would appreciate it wryly. Cocktail waiters divine the perfect cocktail after a few questions then put on a show creating a truly crafted masterpiece. Perfectly clear and cut ice cubes are fit into glasses as part of the process. The experience is worth every penny.

Edo Sake and Ueno Craft Beer

Of course, sake is the traditional chill-time beverage across the country along with beer. For a glimpse into the history of sake, venture to the border of Yananka and Ueno neighborhoods. The free Yoshida Sake museum is an empty pavilion where sake was sold since the Edo period. While sake is no longer served here you enjoy colorful reminders of old marketing ploys and pictures of the early staff.

Sake posters inside the Yoshida public museum in Ueno

Sake posters inside the Ueno Yoshida public museum

If that made you thirsty cross up the street to the 80-year-old Ueno Sakuragi Atari compound. Here craft beer and BBQ is served inside a home-like space. There are shops, a bakery and cats as well as a guest house. If you’re not ready for midday drinking, the Kabaya coffee shop was taken over from the original family and retains the original showa-style (similar to the 1950’s in the US.) Today the café is run by a young group serving local sweets along with a range of good coffee drinks.

ueno sakuragi atari compound with food and craft beers

The Ueno Sakuragi Atari compound delights with food and craft beers

Coffee seems to be misplacing the Matcha culture in Tokyo which isn’t a bad thing for visitors addicted to the dark brew. Of course, you’ll find Starbucks and other Western brands popping up and their lowering the prices somewhat. However, Matcha love continues and you can enjoy a traditional ceremony in the Yanaka area. See the ad above to reserve a guided experience.

Has this whetted your appetite to experience old Tokyo as well as new? There’s much more to see and do of course. Be sure to explore my next post about cultural experiences and lodging when putting together your Tokyo itinerary.

A very different Tokyo itinerary Pin 1 Putting together a very personal Tokyo Itinerary.