This private 12-day sample trip features a wonderful combination of urban excitement, beautiful landscapes and unique cultural experiences, including the Tokyo metropolis, the Japanese Alps, the ancient capital Kyoto, and the art island Naoshima.

Our sample Japan itineraries are here to inspire you. They are not fixed itineraries, and can be customized or altered in almost any way.

Learn more about trip planning with Boutique Japan.

12 daysAround US ~$900-$1,200 per person per day for 2 or more travelers (see our pricing)Based on your preferred travel dates

Trip Highlights

  • Tokyo, one of the world’s most exciting cities
  • Kyoto, the ancient capital and home to world-class UNESCO sites
  • Onsen (hot springs), skiing & snow monkeys in the Japanese Alps
  • Naoshima’s art and architecture & the stunning Miho Museum
  • Unique culinary and cultural experiences
  • An impeccable mix of stylish hotels & traditional accommodations
  • The chance to ride the world-famous shinkansen (bullet train)
  • And more!

Yasaka no Tou Pagoda Higashiyama District Kyoto Japan

Itinerary Details

Day 1: Welcome to Tokyo, Japan!

On arrival in Tokyo, you’ll be met in the arrivals hall. Our representative will be holding a sign with your name on it, and you’ll be escorted to your private vehicle for the comfortable transfer to your accommodations.

You can fly into Tokyo’s Narita (NRT) or Haneda (HND) airport; this itinerary can also be adjusted to begin in Osaka/Kyoto.

Enjoy your first night in Japan and get ready for your adventure ahead!

Your Hotel in Tokyo: Conrad Tokyo, Cerulean Tower Tokyu Hotel, CLASKA, or similar

Shinjuku Tokyo Japan Panoramic Cityscape
Cityscape in Shinjuku, Tokyo

Day 2: Private culinary tour & free time to explore Tokyo

Your trip will get off to an incredible start with a private tour of Tokyo’s famous Tsukiji Market.

After the tour, your guide will show you around the nearby Ginza area before leaving you with free time to enjoy the rest of the day exploring Tokyo.

The Tokyo metropolis is composed of countless districts, each with its own history, character and highlights. While it’s not possible to see everything (whether you have a few days or even a few months!), we will recommend our favorite spots to ensure you get a great introduction to this incredible city.

tsukiji fish market tokyo japan
Tokyo’s Tsukiji Market

Day 3: Free day in Tokyo

Today you’ll have a full day to explore Tokyo, and you will need it!

Tokyo is one of the world’s most fascinating cities, and just wandering the streets of this megalopolis is a fascinating experience with new sights, sounds and tastes to be had around every corner.

You’ll find everything in Tokyo – history, food, art, architecture, gardens, fashion and more – which is what makes it endlessly fascinating to explore.

Hozomon Gate Sensoji Temple Asakusa Tokyo Japan
Senso-ji Temple, Asakusa, Tokyo

Day 4: Bullet train to Nagano & ryokan stay with onsen (hot springs)

You’ll have one final morning to explore Tokyo before heading to the Japan Alps via Nagano city. First you will board the comfortable shinkansen (bullet train) bound for the city of Nagano.

At Nagano you will change to a local train, however we recommend leaving the station for a detour to visit the famous Zenkoji Temple. Zenkoji is one of Japan’s most important temples, with a history of 1,400 years. The city of Nagano developed around Zenkoji, and the streets leading up to the temple are filled with charming shops.

zenkoji temple nagano japan alps
Zenkoji Temple, Nagano

From Nagano you will take a local train 45 minutes deeper into the mountains, where you will be met and transferred to your accommodations.

You’ll spend a magical night in a lovely hot springs resort town located deep in the northern Japanese Alps. Famous for its proliferation of natural onsen (hot spring) baths, the region attracts visitors throughout the year.

The highlights of your stay here will be the rejuvenating hot springs bath and the multi-course kaiseki meal featuring local specialties and fresh local ingredients.

Your Ryokan in Nagano: Aburaya Tousen, Jinpyokaku, or similar

japanese onsen hot spring rotenburo open air bath
Japanese onsen (hot springs)

Day 5: Snow Monkeys & travel to Hakuba ski resort

This morning you’ll visit the Snow Monkey Park in Jigokudani. Jigokudani literally means “Hell’s Valley” – so named for the steam and boiling water that bubble out of small crevices in the frozen ground – and it is in the baths of this boiling water that the resident Japanese Macaques like to soak.

From the gate of the Snow Monkey Park it is about a 25-minute walk to the pools where the monkeys bathe. They live in large social groups, and it can be quite entertaining to watch their interactions. Accustomed to humans, they can be observed from very close and almost completely ignore their human guests.

Central Japan snow monkeys Nagano Jigokudani
Japan’s famous Snow Monkeys

Afterwards, your driver will meet you at your ryokan for the trip to the fantastic ski area of Hakuba, one of Japan’s finest ski towns, which offers a great mix of slopes and social life.

In Hakuba you’ll stay at Hakuba Sierra Resort Hotel, nestled amongst breathtaking natural surroundings. Hakuba Sierra Hotel boasts both indoor and outdoor hot springs baths, excellent access to the slopes, and remarkably friendly service.

Your Hotel in Hakuba: Hakuba Sierra Resort Hotel or similar

Day 6: Skiing or snowboarding in Hakuba

Today you’ll have a full day to enjoy the slopes with your Hakuba Ski Pass.

In addition to skiing and snowboarding, you can also partake in snowshoeing, nighttime ski walks, classic cross-country in the foothills of Hakuba – or simply enjoy Hakuba’s hot springs and nightlife.

Japan Alps view from Hakuba village Aoni in winter

Day 7: Travel to Kyoto

Today you’ll travel to the ancient capital, Kyoto. Today’s train trip takes a few hours, so to make the ride most enjoyable make sure to pick up an eki-ben (train station bento lunch box).

Kyoto is one of the most culturally rich cities in Asia, and the world. Home to 17 UNESCO World Heritage sites, over 1,600 Buddhist temples and 400 Shinto shrines, this ancient city showcases the heart and soul of traditional Japan.

Your Accommodations in Kyoto: Hotel Kanra Kyoto, Hyatt Regency Kyoto, a beautifully-restored machiya townhouse, or similar

Sunset from Kiyomizudera Kiyomizu-dera Buddhist temple UNESCO world heritage site Kyoto Japan
Sunset from Kiyomizu-dera Temple, Kyoto

Day 8: Private tour to introduce you to Kyoto

While it’s possible to enjoy Kyoto unguided, a local expert guide will undoubtedly enhance your experience in ways you would never imagine. Having a guide to peel away the layers and help you explore the hidden nooks of the city will make your short time in Kyoto much more powerful and meaningful.

At first glance, Kyoto looks like almost any other Japanese city. But the discerning eye will soon pick out Kyoto’s treasures: sacred shrines tucked in among shopping arcades, time-honored teahouses nestled among modern businesses, and charming geiko scuttling down backstreets heading to evening appointments.

Kyoto’s charm lies in these details, and whether you’re here for three days or three years, the closer you look, the more you’ll discover.

geisha geiko maiko kyoto japan
Maiko (apprentice geisha) in Kyoto

Day 9: Day trip to the Miho Museum

Today you will visit the stunning Miho Museum.

An easy day trip from Kyoto – located in rural Shigaraki – the Miho Museum was designed by the renowned architect I.M. Pei.

An experience all its own, you’ll find awe-inspiring architecture and world-class artifacts from ancient civilizations. While there be sure to eat lunch at the cafe, the delicious meals are prepared using produce grown on the museum’s grounds.

Miho Museum Tunnel

Day 10: Travel to the art island, Naoshima

Today you’ll make the journey by bullet train – followed by local train and ferry – to the famous art island of Naoshima.

Naoshima – a small island in the Seto Inland Sea – could easily be another pretty, but forgotten island scraping a living from fishing. However, a unique art project pioneered by the Benesse Corporation, has transformed Naoshima into a world-class art destination.

Today, Naoshima is home to a large collection of contemporary art museums, galleries, exhibits and installations, which offer a tour de force of architectural expression integrating art and the natural environment.

Two of the main museums – the Chichu Art Museum and Benesse House – were designed by the world-famous architect Tadao Ando, and feature works by Claude Monet, Walter de Maria, James Turrell, Andy Warhol, Richard Long and Bruce Nauman, among others.

Honmura, a small port town on Naoshima’s eastern coast, is home to the Art House Project, a collection of abandoned houses, workshops, as well as a temple and a shrine that have been converted into art installations and venues for contemporary art by artists and architects from Japan and abroad.

The art houses are scattered throughout town, and most of them are unassuming from the street, blending into the surrounding traditional Japanese neighborhood. The interior of each, however, has been given over to artists to convert into whatever suits their artistic vision.

Your Hotel in Naoshima: Benesse House

Kyushu Japan Naoshima Island Art Yayoi Kusama Pumpkin Sculpture
Yayoi Kusama’s Iconic Pumpkin Sculpture, Naoshima Island, Shikoku

Day 11: Return to Tokyo for final evening

You’ll have part of the morning to enjoy Naoshima, before it’s time to make the return journey to Tokyo.

Enjoy your final evening in Japan!

Your Hotel in Tokyo: Conrad Tokyo, Cerulean Tower Tokyu Hotel, CLASKA, or similar

Day 12: Departure from Tokyo, Japan

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

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

You can depart from Tokyo’s Narita (NRT) or Haneda (HND) airport; this itinerary can also be adjusted to end in Osaka/Kyoto.