An active and eclectic 12-day Japan itinerary featuring the Tokyo metropolis, the Snow Monkeys in the Japanese Alps, a scenic hike on the historic Nakasendo Road, the ancient capital Kyoto, the art island Naoshima, and food-obsessed Osaka.

Let us create your trip completely from scratch.

Our sample itineraries are here to inspire, but this is not a fixed itinerary and is designed to be customized around you.

12 daysUS $900 per person per day and up (our pricing)Private trip based on your preferred travel dates

Itinerary Highlights

  • An immersive private itinerary, crafted with love by Boutique Japan
  • Tokyo, one of the world’s most exciting cities
  • Historic Nagano and the Snow Monkeys in the Japan Alps
  • The Nakasendo Way and the picture-perfect village of Tsumago in the rural Kiso Valley
  • Kyoto, the heart and soul of traditional Japan
  • Stunning art and architecture on Naoshima, including a stay at Benesse House
  • The fun-loving, food-obsessed city of Osaka
  • All your accommodations, in boutique and luxury hotels and ryokans to match your taste and priorities
  • Unique private tours and experiences with fun and knowledgeable local experts
  • Seamless logistics and in-country transport via the shinkansen (bullet train) and more
  • Extensive pre-departure information to help you prepare for your trip
  • Access to our in-depth Japan expertise, relationships, and firsthand experience
  • A Japan specialist to answer your questions, and thoughtful customer service

Vermillion torii gates of Fushimi Inari Taisha Shrine in Kyoto, Japan

Itinerary Overview

Fly into either of Tokyo’s airports, Narita (NRT) or Haneda (HND).

This sample itinerary can also be customized to begin in the Kansai region (where Kyoto and Osaka are located), flying into either of Osaka’s two major airports, Kansai (KIX) or Itami (ITM).

Day 1: Arrive in Tokyo, Japan
Day 2: Modern Tokyo Highlights & Evening Whisky Tasting
Day 3: Backstreets Cycling Tour of Tokyo
Day 4: Shinkansen (Bullet Train) to Nagano & the Japanese Alps
Day 5: Morning Snow Monkeys & Afternoon Travel to the Kiso Valley
Day 6: Walk Along the Nakasendo Way from Magome to Tsumago
Day 7: Morning in Tsumago & Travel to Kyoto
Day 8: Unique Highlights of Kyoto (On & Off The Beaten Path)
Day 9: Day Trip to Shigaraki for the Miho Museum & Pottery
Day 10: Fushimi Inari Shrine & Travel to Naoshima
Day 11: Daytime Explorations of Naoshima & Evening Culinary Outing in Osaka
Day 12: Depart Japan

Depart from either of Osaka’s airports, or customize this trip to end with departure from Tokyo or elsewhere in Japan.

Itinerary Details

Day 1: Arrive in Tokyo, Japan

Welcome to Japan! On arrival in Tokyo, you’ll be met and transferred by private vehicle to your luxurious accommodations.

Depending on your flight’s scheduled arrival time we typically recommend keeping your first evening free, both in case of unexpected flight delays, and also to account for possible fatigue from the long journey.

Settle in, adjust to your exciting new surroundings, and get ready for your adventure ahead!

Your Tokyo hotel: Palace Hotel Tokyo or Andaz Tokyo

Skyline of the Shinjuku district in Tokyo, Japan

Day 2: Modern Tokyo Highlights & Evening Whisky Tasting

Ohayou gozaimasu (good morning)!

Today is your first full day to begin taking in the Tokyo metropolis. You’ll begin with an immersive half-day tour introducing you to the city, and end with a memorable Japanese whisky tasting.

After a delicious breakfast at your hotel, you’ll be met by your insightful private guide. While Tokyo can certainly be enjoyed without a guide, exploring with a fun and knowledgeable expert by your side will dramatically enhance your experience.

At Boutique Japan, we have exceedingly high standards when it comes to private guides, and carefully design each private tour to cater to your unique priorities and interests.

Tokyo is one of the world’s liveliest cities, full of amazing restaurants, beautiful gardens, stunning modern architecture, charming backstreets, and a glittering neon-filled cityscape. Beyond the city lights and crowds, Tokyo is also full of quiet neighborhoods where you’ll find locals going about their daily lives, and countless hidden gems in the form of unsung yet wonderful little shops and restaurants.

Explore unique neighborhoods such as (for example) Naka-Meguro, Yanaka, Aoyama, Omotesando, and Asakusa; along with one or more excellent museums, shrines, or gardens such as the Tokyo National Museum, Meiji Jingu Shrine, and Shinjuku Gyoen National Garden (explore more of our favorite Tokyo neighborhoods).

Following your fascinating tour, you’ll have some time to relax at your hotel and recover from any remaining jet lag you may have, or continue exploring independently. For your free time, you’ll be able to take advantage of the pre-departure materials we provide to each of our travelers.

This evening you’ll venture out on an immersive Japanese whisky tour. Japanese whisky is world-renowned for good reason, and there are few better places to drink it than in Tokyo, which is home to some of the best whisky bars on the planet. As part of your outing you’ll visit a couple of different bars, where you’ll have the chance to sample a variety of excellent Japanese whiskies.

Meiji Jingu shrine in the Harajuku neighborhood of Tokyo

Day 3: Backstreets Cycling Tour of Tokyo

Most first-time visitors envision Tokyo as an ultra-dense, crowded metropolis. While it’s certainly true that some of Tokyo’s neighborhoods do live up to this neon-filled hype, much of the city is composed of surprisingly quiet and charming districts.

Today you’ll experience the quieter side of Tokyo as you embark on a leisurely private cycling tour of the city (urban cycling experience not required). Tokyo is a truly wonderful city for cycling, filled with eclectic neighborhoods along with polite and orderly drivers.

If you’re not interested in cycling, this tour can be modified and made into a backstreets walking tour instead.

Under the guidance of your expert private guide, you’ll wind your way through the slow-paced backstreets of a selection of colorful, off-the-beaten-path neighborhoods. As you explore these non-touristy areas, you’ll also have the chance to stop for casual street snacks along the way.

Your tour will conclude in a lively neighborhood, the perfect place to spend a couple of hours strolling, eating, people watching, or shopping. After some downtime this afternoon, head out for an incredible sushi meal or a taste of Tokyo’s legendary nightlife.

Sushi chef at authentic sushi shop in Japan

Day 4: Shinkansen (Bullet Train) to Nagano & the Japanese Alps

Enjoy a final morning free in Tokyo with the chance to visit Tokyo’s Tsukiji Market if you wish. While the wholesale section of the fish market moved to Toyosu in 2018, Tsukiji’s lively outer market remains an incredible place to immerse yourself in Japanese cuisine.

Then it’s time to leave the city for the mountains.

Today you’ll have your first experience traveling on Japan’s remarkable trains. To begin your journey into the Japanese Alps, you’ll be speeding northwest into central Japan via Japan’s iconic shinkansen (bullet train), a wonderfully pleasant way to travel. Before you depart, take some time to shop for a beautiful bento box lunch to enjoy on the journey (major train stations in Japan offer an astounding variety of delicious seasonal bentos).

On arrival at Nagano Station, you’ll make the easy change to a local train headed deeper into the Alps. But before you continue on your journey, you will have a couple of hours to stroll the charming streets of Nagano City itself.

It’s a nice walk (or short taxi ride) from Nagano Station to the magnificent Zenko-ji, one of Japan’s most important temples, with a history of 1,400 years. The small city of Nagano developed around the temple complex, and the streets leading to Zenko-ji are lined with old-fashioned shops.

Leaving Nagano, it’s a short trip by local rail to your destination for the evening. You have the option to stay in a traditional Japanese-style ryokan in a quaint onsen (hot springs) town, or a small and stylish boutique hotel in the beautiful little historical town of Obuse.

Enjoy a relaxing evening in rural Japan in preparation to visit the Snow Monkeys tomorrow morning.

Your Alps ryokan or hotel: Jinpyokaku Honten or Masuichi Kyakuden

Shinkansen bullet train conductor Japan

Day 5: Morning Snow Monkeys & Afternoon Travel to the Kiso Valley

This morning you will have the chance to visit Japan’s iconic Snow Monkeys, before spending the night in the picturesque village of Tsumago in the Kiso Valley.

From the entrance to the Snow Monkey Park (Jigokudani Yaen Koen), it’s about a half-hour walk to the onsen where the famous Japanese Macaques bathe. In winter the trail is often covered in deep snow, so you’ll need to dress appropriately!

Following your morning adventure, this afternoon you’ll make the easy trip south by rail into the scenic and historic Kiso Valley.

This afternoon and evening settle into the gentle pace of your rural accommodations, located in the idyllic outskirts of Tsumago village. Enjoy a rejuvenating soak in the healing onsen, a healthy and delicious dinner featuring local and seasonal specialties, and the chance to stargaze before bed.

Your Tsumago ryokan: Takimi no Ie or Fuki no Mori

Baby Snow Monkey (Japanese Macaque) at Jigokudani Yaen Koen in Nagano, Japanese Alps

Day 6: Walk Along the Nakasendo Way from Magome to Tsumago

Enjoy an early morning soak in the onsen and a simple Japanese breakfast before your day hike. Today you’ll have the chance to walk along the Nakasendo Road, one of five routes used by samurai to travel between Tokyo and Kyoto during the Edo period.

You’ll begin in the quaint post town of Magome, which lies on a steep slope and is one of the best-preserved towns in the Kiso Valley. From here, you’ll embark on your hike to Tsumago along one of the most carefully preserved stretches of the Nakasendo (a hike of approximately 3-4 hours).

On arrival back in Tsumago, you’ll have the remainder of the afternoon free. Tsumago is one of the Nakasendo’s most beloved post towns, with good reason. The village’s residents have done their utmost to preserve an Edo-era atmosphere, resulting in one of Japan’s most delightful historical villages.

Magome village, a post town on the Nakasendo Way en route to Tsumago in the Kiso Valley, Japan

Day 7: Morning in Tsumago & Travel to Kyoto

Enjoy your final morning in the Kiso Valley. When it’s time to depart, you’ll travel by rail (including another ride on the shinkansen) to the ancient capital, Kyoto.

Kyoto is one of the most culturally rich cities in the world, and the place most travelers dream of when envisioning Japan. Home to 17 UNESCO World Heritage sites, Kyoto was the capital of Japan for over a thousand years and remains the heart and soul of traditional Japan.

Today it is a large modern city of over a million residents, and at first glance looks almost like any other Japanese town. But the city retains many of its long-established traditions, and despite the neon and concrete prevalent in many parts of town, Kyoto is teeming with beautiful and well-preserved pockets where time seems to move more slowly.

You’ll have part of the afternoon free to settle in and adjust to your new surroundings.

In the early evening, you’ll head out on a fascinating private walking tour through the backstreets of Kyoto’s best-known geisha district, Gion. As you slowly meander your way through the narrow lanes and hidden alleys of this enigmatic district, your expert guide will teach you about the history and reality of Kyoto’s geiko (as geisha are called in Kyoto) and maiko (apprentice geisha).

This is a great way to learn about Japan’s most misunderstood traditional profession, and it’s likely you’ll come across geiko or maiko en route to their evening appointments.

Your Kyoto hotel: Hotel Kanra Kyoto or Hyatt Regency Kyoto

Geisha Maiko in colorful kimono in Gion district of Kyoto, Japan

Day 8: Unique Highlights of Kyoto (On & Off The Beaten Path)

Kyoto is full of famous sights, but to experience the city on a deeper level it’s also essential to spend time wandering off the beaten path.

No trip to Kyoto would be complete without visiting some of its remarkable temples, shrines, and gardens. For your time in the ancient capital, you will have the chance to take in an exceptional selection of Kyoto’s gems, carefully curated around your unique priorities and interests.

Explore Kyoto highlights such as (for example) the historic Higashiyama district, the charming Philosopher’s Path, and the picturesque Arashiyama district, along with off-the-beaten-path strolls through lesser-known Kyoto areas with your expert guide.

Kyoto is also rightly renowned for its cuisine and artisans. The colorful Nishiki Market is crowded but a must-visit for food and market lovers. For travelers interested in the arts and traditional crafts, the chance to visit with a shokunin (master craftsperson) in their private workshop is an unforgettable experience.

Beyond the extraordinary sights and wealth of traditional culture, Kyoto is also home to a booming creative scene, and throughout the ancient capital you’ll also find stunning modern design in museums and galleries, along with shops and cafes.

Following your private tour you’ll have the remainder of your day to relax at your lovely hotel, or continue exploring independently making use of the pre-departure materials we provide to each of our travelers.

vegetables outside a traditional wooden restaurant in kyoto, japan

Day 9: Day Trip to Shigaraki for the Miho Museum & Pottery

You will not run out of things to see and do in Kyoto, but rural Shigaraki in Kyoto’s outskirts makes for a wonderful day trip.

Begin at the gorgeous Miho Museum, located on a scenic mountainside. Designed by architect I.M. Pei, the striking Miho Museum houses the private collection of Mihoko Koyama, and includes Asian and Western antiques, as well as works from various ancient civilizations (the museum is closed for a large part of every year).

Afterwards, explore Shigaraki, one of Japan’s most important centers for pottery. Renowned as one of Japan’s six ancient kilns, Shigaraki is famous for the quality of its clay, evident in the lovely shigaraki-yaki (Shigaraki ware).

Day 10: Fushimi Inari Shrine & Travel to Naoshima

Before traveling to Naoshima this morning, you’ll have one final early-morning adventure in Kyoto.

An early start is necessary, as you’ll be visiting Fushimi Inari Taisha, one of Japan’s most famous sightseeing spots. Fushimi Inari is worth visiting even for people who generally avoid “touristy” places, and the easiest way to avoid crowds is by arriving early!

Afterwards, begin the easy trip to the art island of Naoshima, a must-visit destination for art and architecture lovers. The island offers a truly beguiling combination of beautiful natural scenery, charming fishing villages, and cutting-edge modern art and architecture that blend into the coastal landscape.

The journey to Naoshima is easy, with a smooth ride on the shinkansen, an effortless private transfer to the tiny Uno Port, and a short ferry across to the island. As a guest of the one-of-a-kind Benesse House, which doubles as a hotel and museum, you’ll have access to the convenient hotel shuttle making the rounds of the island’s various art sites.

Enjoy the afternoon taking in the island’s museums, galleries, and installations. Among Naoshima’s many highlights are the stunning Chichu Art Museum, the Art House Project, the Lee Ufan Museum, and Benesse House itself.

You’ll spend the night at the Tadao Ando-designed Benesse House, which overlooks the Seto Inland Sea. Guest rooms in each of the hotel’s unique buildings (Museum, Oval, Beach, and Park) feature different works of art, and — among other perks — guests of the hotel enjoy special after-hours access to Benesse House Museum.

Enjoy a peaceful evening in the laid-back Setouchi region of Japan.

Your Naoshima hotel: Benesse House

Benesse House Naoshima Japan
Benesse House (Photo: Tadasu Yamamoto)

Day 11: Daytime Explorations of Naoshima & Evening Culinary Outing in Osaka

You will have the full morning and part of the early afternoon to enjoy all Naoshima offers.

After a morning of art, architecture, and island landscapes you will depart for the city of Osaka, retracing your steps by ferry and private transfer, followed by a quick ride on the shinkansen. On arrival in dynamic Osaka, make your way to your luxurious hotel in the heart of the city.

Osaka is perhaps Japan’s most food-obsessed city, and home to Japan’s most outgoing citizens. There is no better way to experience this fun-loving city than through its countless restaurants, street side stalls, izakayas, and hole-in-the-wall bars.

This evening you’ll be met by a local culinary expert who will take you on an immersive private Osaka food and sake crawl. As part of this unique outing, you’ll be sampling food and drink at a small selection of casual and delicious establishments designed to give you an authentic Osaka experience.

The perfect way to celebrate your final evening in Japan!

Your Osaka hotel: The St. Regis Osaka or Conrad Osaka

takoyaki, a casual local culinary specialty in Osaka, Japan

Day 12: Depart Japan

You’ll be free until departure. Depending on your flight time, you may have time for some last-minute explorations (and eating!).

In good time for your departure flight, you’ll be picked up at your accommodations for the comfortable private transfer to your departure airport.

Come back to Japan soon!