We asked Tokyo cycling experts Chad Feyen and Brad Bennett for their favorite cycling routes across Tokyo, from leisurely park runs for easygoing newbies to thigh-burning, X-Game-level slaloms for adrenaline junkies.

In this post, follow Bennett’s “The Way to the Bay.”  Need some open skies in your life? Then this is the route for you, taking you all the way to Tokyo Bay. Follow either via Google Maps on your phone as you ride or on our site before you head out.

Route length 11km
From Shimokitazawa
To Shinagawa

1. Daichari Bike Rental

If you don’t have your own bike, you can start your journey at this rental spot and pick up one of the electrically assisted bikes. To use the service:

1. Download the HelloCycling App or use the HelloCycling website
2. Create an account
3. Register a form of payment
4. Select from the map where and which bike to reserve
5. Complete your reservation by following the on-screen instructions

You can drop your bike off at any Daichari Bike Rental spot across Tokyo. The app will also tell you how much charge each bike has so you can make sure there is one fully charged before you head to the rental spot to pick one up.

2. Bookends Coffee Service

Fuel-up on caffeine at this little Shimokitazawa coffee shop before your cycling journey to Yoyogi Park.

3. Sky Garden

Have a combini lunch in the sky at the “Sky Garden.” It’s the perfect urban oasis for a quick breather. Over 1,000 trees grace the garden, including cherry blossoms and pine. See if you can spot the vine trees that residents use to make wine. You might get lucky with a view of Mt. Fuji on a clear day! Free admission.


The biggest Starbucks in Tokyo, this spot houses the roasting factory on the fourth floor, with each floor below devoted to a different type of Starbucks hangout. The first floor is a bakery and café, the second is a Teavana tea room and the third is an Arriviamo cocktail bar. The fourth floor factory also has a lounge area and workshop space. There’s also an outdoor terrace seating that overlooks the Meguro River.

5. Shinagawa Bridge

The Shinagawa Bridge is a breathtaking architectural form of stonework. From here you can head over to Tennozu Isle for a meal at T.Y. Harbor, or, if you are adventurous, follow the old tokaido (road) all the way to Yokohama! Tennozu Isle is well-known for its waterfront district with galleries and murals on trendy Bond St., plus the Sea Fort Square boardwalk.


A Tennozu area landmark overlooking the canal and the waterfront lounge, T.Y Harbor is a gorgeous brewery/restaurant down near Tokyo Bay. Here,  you can enjoy a variety of traditional and modern American classics with T.Y. Harbor Brewery’s very own craft beer.

More bike ride routes in Tokyo

  • “Riverside Ride”

    Packed with shrines, parks and hanami gems, this route traces the Kanda River from Sasazuka all the way to the western suburb of Kichijoji.

  • “Yoyo-Go”

    Beginners and families who just want a pleasant, relaxing Saturday afternoon cycle through the city should check out this route, starting from trendy Shimokitazawa and ending at Yoyogi Park. 

  • “Shinjuku Sprint”

    This route is not fun, but you will get to Shinjuku quick. A helmet will make you feel somewhat safer on this one – adrenaline junkies will love it.

  • Tokyo Tower Tour”

    Need some open skies in your life? Then this is the route for you, taking you all the way to Tokyo Bay.


Illustration work by @aprileit