Skift Take

As a rule we shy away from holiday travel, but Tokyo in winter is something we can get behind.

Colin Nagy, head of strategy at Fred & Farid, a global advertising agency, writes this opinion column for Skift on hospitality, innovation, and business travel. “On Experience” dissects customer-centric experiences and innovation across hospitality, aviation, and beyond. 

If you haven’t booked something for the holiday break yet, here’s a provocative idea.

My ritual for the past six or seven years has been to fly into Japan for the week between Christmas and New Years armed with not much more than a JR rail pass and a few hotels booked, spend a few days in Tokyo seeing friends, shopping and eating, and then winging it a bit with the best train and transport infrastructure around. Despite being a peak travel time on the rails, it is still very easy to get around, into the mountains, or along the length of the country.

It is a soft, calming time to be in Japan and the perfect place to re-set yourself for the New Year. The agonizing heat of the summer has long passed and you avoid the tourist crowds enticed by cherry blossoms in the Springtime. The pressure of a busy city is considerably lowered.

Also, as countless devotees of the country know, it is hugely inspiring from a design, culinary, and hospitality sense. A chiropractic adjustment for your taste.

>> Related: Video: What We Can All Learn from the Modern Supertraveler

Here’s how to make it happen on a whim:


I generally like trying to grab a flight on the 25th or 26th of December, where a lot of people are still tied up with holiday festivities. My family has always gotten the gift giving out of the way on Christmas eve, so it frees me up to make a move the day-of. Grab a JAL or ANA flight (Japanese airlines are general like night and day in terms of service compared to their domestic route competitors) and set sights on Tokyo. If you want to splurge, use some hard earned miles to try out JAL’s First which is arguably one of the best products going.


JR’s first-class rail pass is a bargain for those that live outside of the country. You buy it in advance, get it delivered while you are still stateside (very important) and just validate when you arrive in the country. Then, you simply request what train routes you want to take and everything is locked in.


Tokyo is not a cool boutique type city. Best to stick to the bigger guns, or some of the hotels that cater to creative class folks that want to be close to the action. To treat yourself, opt for the ever-classic Park Hyatt in Shinjuku, or the new pitch-perfect Andaz, which is part of a new development in Toronomon. Hoshinoya and Aman have relatively new high-end offerings, as well. Other options for the more budget minded could be the Granbell or the Cerulean tower around Shibuya. Airbnb is starting to be much more vibrant, in particularly cool areas of the city such as Daikanyama and Nakameguro as well.


Tokyo has no shortage of Michelin stars that require a bit of pre-planning and concierge wrangling. But a lot of the charm is in the one-off, easy lunches and casual food. The best is taking chances and going with the flow. My quick picks are Afuri for Yuzu ramen, Birdland Ginza for Yakitori, Appia for Italian, Ishikawa for Kaiseki, Daiwa, Sushi-ya or former New Yorker Yasuda-san for Sushi, and also Golden Brown in Omotesando for arguably one of the city’s best burgers. And yes, Jiro is that good but both hard to book and it costs a pretty penny. Go if you need to, but don’t hang your trip off of it.


Tokyo is a serious drinking town. Some highlights: Shibuya Swing is a small jazz bar with cozy cocktails and friendly. Also don’t miss Bar Trench, Bar Track, and Bar Radio. Bar High Five typically makes the world’s best bar awards most years, and Bar BenFiddich is worth checking out in Shinjuku, hidden in the ninth floor of an office tower. Worth calling ahead. Also, a crawl through the small, 4-5 seater bars of Golden Gai, a charming and ramshackle place that harkens back to another era of the city. La Jetee should be your main coordinate here, but also let yourself be pulled into wherever intrigues.


21_21 is a very good design museum in Tokyo Midtown, the Mori Museum in Roppongi is meticulously curated and offers stunning views at the top of the Mori Building, The elegant Nezu Museum focuses on Japanese and other Asian pre-modern arts, especially strong in arts related to tea. You’ll notice exceptional curation and attention to detail at all museums, and worth logging some time.


Last year I ushered in the New Year sitting in a private onsen in the mountains of Niigata with thick snowflakes falling on my head and couldn’t have imagined a better way to align the mind and figure out priorities for the upcoming year. Note: the best ones are often hard to book at last-minute notice, (and often requires a native speaker) but some tried and true options are Gora Kadan, Atami Fufu, Sekeitai, Satoyama Jujo, and Lamp No Yado. And if you want to splurge, try the Arcana on the Izu Peninsula.

New Year’s

A note on New Year: hotels are booked up super quickly. And this is not a town for revelry, but more for shrine visits and introspection. And New Years day sees Tokyo turn into a ghost town. So best to fly home, or onto your next destination.

It does sound aggressive, but a short trip to Japan over the break is a tremendous way to re-set your brain, gather some inspiration, and get yourself prepared for the year to come. It is tried and true, and just requires a bit of a leap of faith.


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Tags: japan, On Experience, supertravelers

Photo credit: Shibuya Crossing in downtown Tokyo. A winter getaway to Japan may be more accessible than it seems. Toomore Chiang / Flickr

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