< Designed Trips

The Trip

From skyscrapers, neon lights and bullet trains, to nature, history, ritual and religion, Japan expertly blends innovation and tradition, offering a travel experience unlike anywhere else in the world. On this 11-day Designed Trip, you’ll discover the best of the country’s cities and small towns, with incredible food and rich cultural experiences along the way. Begin in the exciting capital of Tokyo - the largest city in the world, yet safe, orderly and clean. Dive into Japanese cuisine on a local food tour and learn the appropriate way to eat sushi, how to order BBQ at an Izakaya, where to find handmade noodles, and how to thank the chef for a good meal. Uncover both sides of the city, visiting immersive art installations and 3D neon signs while also experiencing the local fish market and one of the country’s most important temples. After Tokyo, you have options. Either hop on a train north to the Kiso Valley for two days of moderate hiking along the Nakasendo Trail, the ancient road that once connected Tokyo and Kyoto. You’ll walk through ancient ‘Post’ towns, traversing ancient cobblestones through bamboo and cedar forests as you search for wild forest monkeys. Alternatively, visit the mountain village of Hakone, famous for its forested Onsens - Japanese natural hot springs. Either way, sleep in the silence of traditional Ryokans and embrace the quiet nature that is a cornerstone of Japanese culture. Finally, it’s on to the ‘city of ten thousand shrines,’ Kyoto, to visit some of the country’s most important landmarks, learn about Geisha, and take part in ancient rituals like a traditional matcha tea ceremony. If you’d like, hop on a short train to Osaka for a street food feast, or Nara, to hang out with 1,200 friendly wild deer. On your journey through Japan, you’ll travel by efficient trains, indulge in some of the healthiest cuisine in the world, and soak up the intangible energy of this beautiful and exciting country.

The Details

Price: 
  • From $3,668 per person
Duration:
  • 11 days, 10 nights
Inclusions:
  • Highly-rated boutique hotels
  • Transportation within Japan
  • Small-group experiences
  • Curated destination mini-guide
  • Trip preparation & support
Exclusions:
  • International flights to Japan (Flying into Tokyo and out of Osaka is recommended)
  • Meals & activities not listed
  • Travel insurance

Japan FAQs

WHEN IS THE BEST TIME TO VISIT JAPAN?
​Generally, spring (March-May) and fall (September-November) are considered peak seasons and the best time to see the cherry blossoms (early April) and fall foliage. However, winter months can also be a great time to visit. We would recommend avoiding the rainy season in June and July. 
WILL I HAVE A HARD TIME COMMUNICATING?
Most people who work in tourism do speak English. Generally, people are very kind and patient, so if you can’t communicate, Google translate can be a big help. The photo feature can also be very helpful to read signs and packaging.
IS IT SAFE?
​Japan is incredibly safe with one of the lowest crime rates in the world.
How difficult is the nakasendo trail hike?
​The two days of hiking we have included in the Designed Trip are each about 5-6 miles and generally take about 2-3 hours to complete. Please let us know if you are concerned about the intensity of the hike and we can provide more details.
can i add more time to the nakasendo trail hike?
​If you have the energy and want to add an additional day of hiking, there is a longer (and very scenic) ~11-mile stretch that winds through bamboo forests and past rice fields. Let us know if you’re interested!

The Itinerary

Tokyo

  • Day 1: Konnichiwa, Japan! Step off the plane and meet your private driver who will take you to your hotel in the bustling city center to check in and get settled. The sun sets early all year round, so after dark, sit down to your first dinner of handmade noodles (ramen, soba or udon), or fresh sushi ordered on a screen and arriving on a conveyor belt. 
  • Day 2: After a big breakfast, hop on the (efficient and easy-to-use) subway to the Shibuya district. When you picture Tokyo, this may be what you envision. Giant skyscrapers, neon lights, and one of the most iconic sights in the city: the Shibuya Shuffle, where upwards of 3,000 people cross a busy intersection at one time. After exploring the area, hop back on the subway to another one of the liveliest districts: Shinjuku. Meet a local guide for an evening food tour of the area, stopping at a tiny Izakaya, a hidden sushi restaurant, an incredible ramen house while passing by the iconic Godzilla and red light district before ending in the historic Golden Gai neighborhood.
  • Day 3: Now that you’ve experienced the modern lights of the city, it’s time to dive into some history and culture in one of the oldest (and most sacred) districts, Asakusa. Meet a small group for a guided tour of the early Buddhist Senso-ji Temple, the single most visited religious site in the world, before exploring Ueno, where street vendors have been selling wares for generations, and Akihabara, an area known for electronics, anime, and all things pop-culture. The afternoon can be spent exploring Hie Shrine or the Imperial Palace before sitting down to a big bowl of noodles. 
  • Day 4: Good morning! Wake up and drink hot matcha before heading to the famous Tsukiji Fish Market. Browse the outdoor markets, stopping for sashimi made with the highest quality fish in the city, as well as other treats like mochi and tamagoyaki. In the afternoon, experience an immersive, multi-sensory experience at either teamLab Borderless or teamLab Planets as you walk through incredible exhibits of projection mapping, music, lights and effects unlike any other art museum in the world. ​​

- Nakasendo Trail Hike -

  • Day 5: After four days in the hustle and bustle of the world’s largest city, it’s time to trade skyscrapers for cedar forests and Shinto shrines. In the morning, hop on a short, 2-hour train from Tokyo to Magome, one of the most picturesque port towns along the historic Nakasendo Trail. Spend the afternoon hiking the first 2-hour stretch along the trail, once the ancient stone road that connected Tokyo and Kyoto. Arrive in the historic village of Tsumago in the afternoon, check in to your traditional hotel and be greeted by your luggage before a hearty dinner and a good night’s sleep.
  • Day 6: After breakfast, take a short regional train to the town of Yabuhara, and the gateway to the beautiful Torii Pass. Spend the next few hours making your way up the mountain, passing ancient forested shrines and taking in views of the Kiso Valley below. The trail ends in the historic port town of Narai where you can hop on a short train (or opt for a transfer) to the small city of Matsumoto. Check in to your cozy ryokan (Japanese Inn) and enjoy a well deserved dinner before curling up on a traditional futon atop tatami mats.
  • Day 7: You’re in no rush this morning, so take the time to enjoy your traditional Japanese breakfast before exploring this small vibrant city. Head to Matsumoto Castle, a designated national treasure and one of the finest examples of structures that survived the post-feudal ages intact. Remove your shoes and explore the interior wooden stairs, windows used to drop stones onto invaders, and openings once used for archers. After lunch, hop on a high-speed train to the city of Kyoto, and your home for the next four nights. As one of Japan’s most popular destinations, Kyoto is famous for its zen gardens, imperial palaces, Buddhist temples, and Shinto shrines, as well as its traditions like the multiple-course kaiseki dining, and geisha, who still reside in okiya within the Gion district. Spend the rest of the day exploring the lively city, strolling through the beautiful historic districts or along the riverside pathway before sitting down to a delicious dinner.

- Hakone - 

  • Day 5: After four days in the hustle and bustle of the world’s largest city, hop on a short ~90-minute train to the peaceful town of Hakone, best known for its volcanic hot springs (onsen) and views of Mount Fuji as well as waterfalls, hiking trails and nature. After arriving, change lines to the local train that will travel up the mountain to the small town of Gora, famous throughout Japan for its traditional ryokan inns with forested onsen. Spend the remainder of the day soaking in the hot, healing waters before sitting down to a traditional multi-course kaiseki dinner at your hotel. 
  • Day 6: Wake up to the quiet nature of the peaceful forest. The day is free to explore the area surrounding Hakone. You  may want to hop on the short train down to Lake Ashinoko (or ‘Lake Ashi’), formed in the caldera of Mount Hakone after the volcano's last eruption 3000 years ago. Or, go on a short (~2 hour) hike along the Tokaido, one of the primary routes that connected Tokyo and Kyoto during the Edo Period. Grab lunch in the Sengokuhara area to see the surrounding Susuki, beautiful Japanese silver grass that is famous in the area. Spend the afternoon checking out the Hakone Open Air Museum, considered one of the world's most spectacular sculpture parks, or the famous Hakone Shrine, tucked in the forest with an impressive lakeside torii gate dating back to the Heian Period. Or take the Hakone Komagatake Ropeway up to  Mototsumiya ("original shrine") a second, older shrine that stands at the summit of Komagatake, one of Mount Hakone's multiple peaks, and is known for being blanketed in a constant cloud of mist. 
  • Day 7: After a quiet morning and a relaxed breakfast, pack up and check out of your hotel before hopping on a high-speed train to the city of Kyoto - your home for the next four nights. As one of Japan’s most popular destinations, Kyoto is famous for its zen gardens, imperial palaces, Buddhist temples, and Shinto shrines, as well as its traditions like the multiple-course kaiseki dining, and geisha, who still reside in okiya within the Gion district. Spend the rest of the day exploring the lively city, strolling through the beautiful historic districts or along the riverside pathway before sitting down to a delicious dinner.

Kyoto

  • Day 8: Although Kyoto is a large city, it’s made up of a grid of primarily small, narrow streets with little traffic, making it perfect to explore by bike. Choose to join a small-group guided bike tour, or pick up rentals for an independent ride, visiting some of the city’s best and off the beaten path temples and shrines while cruising through local neighborhoods. In the afternoon, head to Arashiyama, a naturally beautiful area tucked alongside the hills and most famous for its towering bamboo forest and monkey forest, along with river boats, various small museums and temples. Enjoy dinner nearby or in one of the city’s historic neighborhoods like Pontocho and Kiyamachi, ducking into a traditional izakaya for casual bbq or sitting down to a more formal sushi dinner or multi-course kaiseki dinner.
  • Day 9: Matcha, a distinctive variety of green tea leaves that are cultivated with care and eventually ground into a fine powder, has been grown nearby for over 800 years. Spend the morning diving into the history and tradition of matcha tea on a unique food and cultural tour. Explore Kyoto’s Uji district, sit down to a local lunch, experience a traditional tea ceremony (a ritual that dates back to the 1600’s), and learn what goes into the production of the world’s best matcha tea. The afternoon is free to explore, walking through Nishiki Market, a 5-block long street lined with more than 100 stalls, shops and restaurants, walking the pretty Philosopher's Path, or visiting one of the 1600 temples or 400 shrines in the city. After the sun goes down, meet a local guide for a short walk through Gion Shirakawa, the most beautifully preserved part of the Gion district. Take in the traditional architecture and the glow of hanging lanterns as you learn about the art and history of geisha, beautiful and highly respected dancers and entertainers that have lived and worked in this neighborhood for centuries. 
  • Day 10: Your final full day in Japan can be spent further exploring the shrines, temples and sights of Kyoto (there is plenty to see!) or hopping on a train for a day trip outside of the city. Choose to either visit Osaka, the third largest city in Japan nicknamed ‘the City of Merchants’ and well known for its street food scene. Alternatively (or in addition, if you’re feeling energetic), check out the small city of Nara, famous for its 1200+ wild deer that freely roam the city, the historic Kasuga Taisha Shrine and freshly pounded mochi rolled in sesame flour and stuffed with sweetened red bean paste.
  • Day 11, Kyoto: Wake up in the ancient capital city, oozing with culture and tradition. After your final bowl of miso soup and cup of green tea, pack up and check out of your hotel. A private driver will pick you up at your hotel for the short drive to Osaka airport for your flight home. (Or, if you’d like to continue the adventure, ask us about adding on another destination in Asia!) Step on the plane with tired feet, full bellies and many memories made as you say sayōnara to Japan.

Pricing & Inclusions

Boutique
  • Tokyo, 4 hotel nights
  • Nakasendo Trail -OR- Hakone, 2 hotel nights
    • Based on availability
  • Kyoto, 4 hotel nights: 
  • Japan Rail Pass 
  • Shinjuku and Golden Gai food and cultural small group tour 
  • Asakusa, Uneo, and Akihabara tour with Senso-ji Temple
  • Entry tickets to Teamlab Borderless or Teamlab Planets
  • Bike rentals (e-bikes) or small group temple bike tour
  • Matcha food and cultural tour of Kyoto
  • Kyoto Gion Geisha District Walking Tour
  • Curated destination guide
  • Trip preparation & support






​
​Exclusions
  • International flights to Japan (Flying into Tokyo and out of Osaka is recommended)
  • Meals & activities not listed 
  • Travel insurance
​
Boutique Pricing
  • From $3,668 per person w/ Nakasendo Trail
  • From $3,795 per person with Hakone
​
​*Pricing based on double occupancy and may vary depending on travel dates and total number of travelers. ​
Luxury Boutique
  • Tokyo, 4 hotel nights
  • Nakasendo Trail -OR- Hakone, 2 hotel nights
    • Based on availability​​
  • Kyoto, 4 hotel nights: 
  • Private arrival airport transfer, Tokyo
  • Japan Rail Pass 
  • Shinjuku and Golden Gai food and cultural small group tour 
  • Asakusa, Uneo, and Akihabara tour with Senso-ji Temple
  • Entry tickets to Teamlab Borderless or Teamlab Planets
  • Bike rentals (e-bikes) or small group temple bike tour
  • Matcha food and cultural tour of Kyoto
  • Kyoto Gion Geisha District Walking Tour
  • Private departure transfer, Osaka
  • Curated destination guide
  • Trip preparation & support

​
​
Exclusions
  • International flights to Japan (Flying into Tokyo and out of Osaka is recommended)
  • Meals & activities not listed 
  • Travel insurance

Boutique Luxury Pricing
  • From $4,786 per person w/ Nakasendo Trail
  • From $5,110 per person with Hakone

*Pricing based on double occupancy and may vary depending on travel dates and total number of travelers. ​
Luxury
  • Tokyo, 4 hotel nights
  • Nakasendo Trail -OR- Hakone, 2 hotel nights
    • Based on availability
  • Kyoto, 4 hotel nights: 
  • Private arrival airport transfer, Tokyo
  • Japan Rail Pass (First Class) 
  • Shinjuku and Golden Gai food and cultural small group tour 
  • Asakusa, Uneo, and Akihabara tour with Senso-ji Temple
  • Entry tickets to Teamlab Borderless or Teamlab Planets
  • Bike rentals (e-bikes) or small group temple bike tour
  • Matcha food and cultural tour of Kyoto
  • Kyoto Gion Geisha District Walking Tour
  • Private departure transfer, Osaka
  • Curated destination guide
  • Trip preparation & support

​
Exclusions
  • International flights to Japan (Flying into Tokyo and out of Osaka is recommended)
  • Meals & activities not listed 
  • Travel insurance

Luxury Pricing
  • From $6,213 per person w/ Nakasendo Trail
  • From $6,748 per person with Hakone

​*Pricing based on double occupancy and may vary depending on travel dates and total number of travelers. ​

Optional upgrades

  • Private Shinjuku and Golden Gai food and cultural tour 
  • Private Kyoto temple bike tour
  • Private matcha food and cultural tour of Kyoto
  • Tsukiji Fish Market tour in Tokyo
  • Ramen making workshop in Kyoto
  • Kimono rentals with Kyoto tea ceremony
  • Private Kyoto Gion Geisha District Walking Tour

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​This Designed Trip was developed based on our personal travels, with local contacts, favorite hotels and authentic activities we've experienced first-hand.
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Designed Trip FAQs

​WHAT IS A DESIGNED TRIP?
A Designed Trip is a pre-designed travel plan based on our personal, first-hand travel experiences in each destination. As they are pre-designed, our Designed Trips have been created as a turnkey travel option and can be booked and delivered in as little as one week. ​
CAN I MAKE ANY CHANGES TO A DESIGNED TRIP?
Absolutely! Pre-designed doesn’t mean there isn’t any flexibility. Whether you want to shorten or lengthen your trip, switch out a destination or change an activity, let us know. If, however, you want a trip built around your specific desires, a Custom Trip might be more appropriate. We can help you decide, so get in touch.
​HOW LONG DOES THE PROCESS TAKE?
Once you’ve selected your Designed Trip and chosen between a Boutique, Luxury Boutique or Luxury experience, your trip can be booked and delivered in as little as one week. If you would like to make some changes to your trip, such as including an alternative activity, shortening or lengthening your trip, then this can take a bit longer.
HOW DO I KNOW HOW MUCH MY DESIGNED TRIP WILL COST?
Once you have decided on your Designed Trip, your dates, and any adjustments we will provide a personalized itinerary and pricing for your trip. We have included base pricing on each Designed Trip page to give you an idea as to what the final cost might be, but prices can fluctuate depending on time of year and any personalization. Get in touch and we can help.
If you have any other questions, feel free to check out more FAQs or send us an email.