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Your Guide To Planning A 30-Day Workation In Japan

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Here’s the sign you’ve been looking for to finally make that month-long workation in Japan happen!

Jetting off to the Land of the Rising Sun for a change of scenery without compromising productivity sure sounds like an awesome idea, but it is also true that embarking on a workation in Japan requires a good deal of research and preparation, so you can make the most of your extended stay. 

To help you get started, we created this nifty guide for burned-out (or simply curious) souls like you, who just wish to escape the mundane and experience something new. 


Why work remotely from Japan?

As if you need more reasons to choose Japan for your 30-day workation, we’ll tell you this: It ticks all the boxes for the ultimate adventure. Japan—a place teeming with rich cultural heritage that perfectly blends with modern innovation and natural beauty—definitely has something for everyone!

The only major con that we couldn’t deny about staying in Japan for a long period as a digital nomad is the high cost of living. Even with the yen weakening of late, Japan still is an expensive country. Having said that, managing your budget and living comfortably during your workation is doable with the right planning. 


Before You Go

Once you’re dead set on embarking on a working holiday in Japan, there are a couple more things you should consider and prepare. 


If it’s been a while since you last traveled overseas, check your passport if it is still valid for at least six months beyond the time you plan to have your workation. Otherwise, it’s time to renew your passport. 

Visa Requirements

At the moment, Japan still hasn’t launched a digital nomad visa, which means, the closest visa foreigners can get to enjoy both (remote) work and play in Japan is the Designated Activities (Long Stay for Sightseeing and Recreation) visa type, which is available to select nationals and citizens of visa waiver countries or regions. 

If you’re just going for light productivity, though, say answering urgent calls and attending meetings every now and then while you explore the country, a tourist visa, which usually allows stays of up to 90 days, would be enough. 

To make sure that you meet the visa requirements of Japan, you can check with a travel agent in your area or contact the Embassy of Japan directly for all the questions that you have. 


So… where will you stay during your working holiday? 

A quick search online will lead you to countless lodging options in the city and in the countryside, ranging from five-star hotels and well-equipped serviced apartments to hip hostels and well-maintained ryokan (traditional Japanese houses). 

Ultimately, when choosing your accommodation, you would want to book a place that allows for easy access to public transportation and local amenities. 


There is no definitive answer to the question “How much should I prepare for my workation in Japan?” The amount of money you have to set aside will generally depend on the following:

  • The season you’re going (Be ready to shell out more money if you choose to travel during Japan’s peak season, which usually falls around the time when cherry blossoms or sakura bloom.)
  • Roundtrip airfare
  • Accommodation
  • Transport around Japan (Factor in transport passes like the Tokyo Subway Pass or Japan Rail Pass that you’ll be purchasing ahead of time. You can also make an estimation of the amount you’ll need to load into your IC card by searching for routes online. Google usually displays the prices of train rides.)
  • Meals per day
  • Admission fees to popular attractions
  • Spending money for extras (souvenirs, impulse puchases, etc.)

Travel Insurance

Sometimes, mishaps are unavoidable. You can get injured or fall ill during your month-long stay in Japan, and if you’re uninsured, you will easily rack up a bill that might be too steep for you to pay out-of-pocket. 

Carrying travel insurance from a reputable provider gives you a financial safety net in the event that you require medical attention, your airline loses your luggage, or your flight gets delayed.

Time Zone Considerations

If you are working remotely from Japan—which operates on Japan Standard Time (JST or GMT+9)—it is only right that you notify your boss and colleagues about your plans and settle your work schedule with them. 

Make the necessary adjustments to meetings, presentations, and other official matters ahead of time. You might also want to set an alarm for each important event you have to participate in, so you don’t miss out on anything and get in trouble once you return from your working holiday. 

Language Lessons

Learning basic Japanese before your trip will prove to be extremely helpful since only a small fraction of the Japanese population can speak English fluently. 

You don’t have to enroll at a language center prior to your trip (although no one’s stopping you from doing so!) to learn common phrases and sentences that will come in handy during your stay. There are a lot of learning resources online that you can take advantage of to have, at least, a beginner’s level of understanding of Nihongo. 

Whether you choose to take classes or go the self-study route, your efforts to learn basic Japanese will surely pay off!

Internet Connectivity

Having access to a reliable network is crucial for a successful workation. 

You might think it would be easy to access the internet in a country as technologically advanced as Japan, but no. As modern as Japan may seem, free Wi-Fi is not as widely available as you think it would be over there. Moreover, connecting to a public network can put your security at risk in so many ways, and you don’t want that to happen. 

You can proactively secure your sensitive personal data from threats posed by public networks by subscribing to a third-party specialized travel Wi-Fi that is private just for you. A Travel Wi-Fi can keep you private and anonymous to the prying eyes of scammers and hackers. 

Big Sky is the #1 Travel WiFi Provider in the Philippines, specializing in providing internet for both tourists and digital nomads on the go. Best to send an inquiry and request a long-duration package for your workation in Japan. Big Sky will make sure to give you the best rates for your long travel.

Another option is to get a Travel SIM card—just make sure that your phone is not under a lock-up period. Big Sky can give you options for Travel WiFi, Travel SIMs, and Travel eSIMs. You’re in good hands since they’re rated by verified customers as the #1 Travel Wi-Fi and the #1 Travel Connectivity company in the world.

Click here to browse through more internet connectivity options for your trip!


30 Days In Japan: A Sample Itinerary For Your Workation

When embarking on a working holiday, you have to decide whether you will stay in one city for the entire duration of your trip or hop from one place to another. Each has its own advantages and disadvantages, of course, so make sure to think things through before making a decision. 

Assuming you’ll do a multi-city workation and it’s your first time in Japan, we crafted a sample itinerary so you can strike a good balance between play and productivity:

Days 1-10: Tokyo 

Be greeted by the urban buzz of the megalopolis that is Tokyo over the first couple of days of your stay in Japan!

Experience the Japanese capital just like you imagined it and more in bustling districts like Shibuya, Shinjuku, and Harajuku. Get your geek on in Akihabara or go on a cultural tour around Asakusa. Got some extra yen to spare? Hit the shops at Ginza! You’ve got 10 days to enjoy your stop in Tokyo—make every second of it count!

Top 10 Recommended Activities in Tokyo:

  1. Read your fortune at Sensō-ji Temple
  2. Experience tranquility in the middle of the city at Meiji Jingu
  3. Snap a photo with the iconic Tokyo Tower in your background
  4. Get a bird’s-eye view of the megalopolis from Tokyo Skytree’s observation deck
  5. Walk the Shibuya Scramble Crossing
  6. Enjoy fresh sushi at Tsukiji Outer Market
  7. See the gigantic Gundam statue at Odaiba
  8. Sample street food at Asakusa
  9. Visit the only DisneySea in the whole world
  10. Stroll around Ueno Park

Day Trip Opportunities

With Tokyo as your temporary base, you can take a day trip to nearby areas like Yokohama and Yamanashi. 

Yokohama is the largest port city in all of the Kanto region and is home to numerous waterfront attractions like the Yokohama Landmark Tower, Cosmo World, and the Red Brick Warehouse—all of which are located in the Minato Mirai Area. Yokohama Chinatown is also a must-visit if you’re a foodie.

Meanwhile, Yamanashi is where you will catch some of the best views of the majestic Mt. Fuji. With Yamanashi’s natural wonders, a day might not be enough for your visit.


Days 11-17: Kyoto

After Tokyo, make your way to the former Japanese capital Kyoto via plane (to Kansai Airport) or the Shinkansen (to Kyoto Station). A city brimming with history and culture, Kyoto is where the old seamlessly coexists with the new. 

Top 10 Recommended Activities To Try In Kyoto:

  1. Catch the daybreak at Arashiyama
  2. Be stunned by Kinkakuji—a temple covered in gold
  3. Visit Kiyomizudera and set foot on its remarkable wooden terrace
  4. Comb through the souvenir shops at Higashiyama
  5. Make a wish at Fushimi Inari Taisha
  6. Hop on the Sagano Romantic Train for spectacular views of Kyoto’s natural landscape
  7. Don a kimono and walk around Gion District
  8. Take part in a traditional tea ceremony 
  9. Have a go at local delicacies like rice crackers and dried fish snacks at Nishiki Market
  10. Learn more about Japan’s trains at the Kyoto Railway Museum

    Day Trip Opportunities

To see a different side of Kyoto, make your way to Ine, a town situated around Ine Bay in northern Kyoto Prefecture. In the fisherman’s village, you will find funaya or stilt houses that have been around since as far back as the 1700s. 

Alternatively, you can take the train to the nearby city of Nara, where countless temples dating to the 8th century still stand. The city’s biggest draw is Nara Park, where over a thousand deer freely roam about. 


Days 18-23: Osaka

From Kyoto, you can make your way to Osaka via Shinkansen or a Limited Express train. Travel time ranges from 12 to 55 minutes. 

Osaka—also known as “Japan’s Kitchen”—is big on record-breaking sights and gastronomic delights. A bit more laid-back than Tokyo and Kyoto, this city invites you to loosen up and just have fun!

Top 10 Recommended Activities To Try In Osaka:

  1. Visit the 400-plus-century-old Osaka Castle
  2. Feel the retro atmosphere at Shinsekai
  3. Be awe-struck by marine life at Osaka Aquarium—one of the largest aquariums across the globe
  4. Scale the Umeda Sky Building on the world’s highest escalator
  5. Dig into local fare at Kuromon Market
  6. Sink your teeth into authentic takoyaki at Dotonbori
  7. Pose for the quintessential Osaka photo with the Glico Running Man
  8. Ride the movies at Universal Studios Japan 
  9. Get panoramic views of Osaka from the observatory of Abeno Harukas—the highest skyscraper in Japan
  10. Hop on the Ebisu Tower Ferris Wheel a.k.a. the “Don Quijote Ferris Wheel”

Day Trip Opportunity

Continue your foodie tour by heading over to Kobe for a juicy Kobe beef steak!


Days 24-30: Sapporo

After your Kanto and Kansai escapades, fly to Hokkaido Prefecture’s capital—Sapporo!

A familiar name—thanks to the world-famous Sapporo Beer brewery—Sapporo has more to offer than just fizzy alcoholic drinks. Best visited in winter, this city is brimming with snow sport sports as well as natural hot springs!

Top 10 Recommended Activities To Try In Sapporo:

  1. Be astonished by colossal snow sculptures at the Sapporo Snow Festival
  2. Sample different brews at the Sapporo Beer Museum
  3. Try skiing at Teine Ski Resort
  4. Unwind at Odori Park
  5. Rejuvenate your senses at Jozankei Onsen
  6. Learn about Hokkaido’s history at the open-air museum that is Historic Village
  7. See how chocolates are made at Shiroi Koibito Park’s chocolate factory
  8. Climb Mount Moiwa for sweeping views of Sapporo City
  9. Get the freshest produce at Nijo Market
  10. See the neon lights at Susukino—Sapporo’s answer to Tokyo’s Shibuya

Day Trip Opportunity

If you’re visiting during the winter months, do not miss Niseko, Japan’s most popular ski resort. This winter wonderland is known to have the world’s best powder snow. 


Wrapping It All Up

Japan is an excellent choice for a workation. You get to experience its rich cultural heritage, marvel at its technological advancements, and enjoy the country’s beautiful natural scenery. With research and thorough planning, you can certainly make your dream workation in the Land of the Rising Sun happen! 



Planning a short stay in Japan? Stay connected to high-speed internet with your own travel Wi-Fi device from Big Sky Nation, the #1 Travel Connectivity Provider in the World. For as low as 190 PHP, you get to rent a portable travel Wi-Fi device that can accommodate up to five (5) devices. Check out more options here!


***Featured image by Jezael Melgoza on Unsplash