Explore Japan's cityscapes and natural landscapes on this active 13-day adventure that includes an epic, five-day trek along the ancient Nakasendo Trail. Stop in historic post towns, climb mountain passes, soak in hot springs, and relax in charming inns along the way. On either side of your trail hike, discover the shrines and castles of Osaka and Kyoto, take day trips to meet the deer of Nara, and see Mount Fuji on a lake cruise before ending in Tokyo for a city tour and whisky tasting.


  • Step back in time at Osaka Castle, right in the middle of the city
  • Don a kimono for an expert-led tea ceremony in Kyoto
  • Stay overnight in the beautiful post town of Tsumago along the Nakasendo Trail
  • Take in the panoramic views from the top of Usui-toge Pass
  • See the towers and shrines of Tokyo on a city tour

Brief Itinerary

Day Highlights Overnight
Day 1 Arrive in Osaka, Explore at Your Own Pace Osaka
Day 2 Tour Osaka Castle, Umeda Sky Building & Shinsaibashi District Osaka
Day 3 Train to Kyoto, Explore Fushimi Inari-Taisha Shrine & Tofuku-ji Temple Kyoto
Day 4 Temple & Castle Tour, Kimono Tea Ceremony & Samurai Museum Kyoto
Day 5 Day Trip to Nara & Uji Kyoto
Day 6 Train to Magome, Nakasendo Trail (Day 1): Magome to Tsumago Tsumago
Day 7 Nakasendo Trail (Day 2): Tsumago to Nojiri, Train to Kiso-Fukushima Kiso-Fukushima
Day 8 Train to Yabuhara, Nakasendo Trail (Day 3): Yabuhara to Narai Narai
Day 9 Nakasendo Trail (Day 4): Narai to Kiso-Hirasawa, Train to Karuizawa Karuizawa
Day 10 Nakasendo Trail (Day 5): Karuizawa to Yokokawa, Train to Tokyo Tokyo
Day 11 Best of Tokyo Tour Tokyo
Day 12 Day Trip to Mount Fuji with Lake Cruise & Whisky Tasting Tokyo
Day 13 Depart Tokyo  

Detailed Itinerary

Day 1: Arrive in Osaka, Explore at Your Own Pace

Osaka Castle
Explore the Sumiyoshi Taisha on your first day in Osaka

Welcome to Japan! After you arrive at Kansai International Airport, a guide will be waiting to lead you to your hotel shuttle, which will whisk you to the center of Osaka. Settle into your hotel, then head out to explore this lively and beautiful city, often described as Tokyo's younger (and cooler) sibling. See the sights on your own, starting at the incredible Sumiyoshi Taisha. Initially founded in the third century, this history-rich site features classic sumiyoshi-zukuri architecture, with straight roofs and forked finials, and the beautiful Sorihashi Bridge.

End in Hozenji Yokocho, a stone-paved alley tucked away in a quiet corner of the buzzing Namba area and the go-to place for Edo-period atmosphere and local food. Stroll by traditional shops, restaurants, and bars, then stop at its namesake temple of Hozen-ji to make a wish for luck before ducking into a restaurant for a delectable meal of deep-fried skewers of meat and veggies, okonomiyaki (Japanese pancake), or meoto zenzai (red bean soup with rice cakes).

Day 2: Tour Osaka Castle, Umeda Sky Building & Shinsaibashi District

Full Day Osaka Castle, Umeda Sky Building and Shinsaibashi
Explore the sights of Osaka today, including the gorgeous Osaka Castle

Today, meet your guide for a full-day tour of Osaka's most famous sights, such as Osaka Castle and (in spring) its blossom-filled grounds. Delve deep into Osaka's history at the Osaka Museum of Housing and Living, a detailed recreation of the townscape throughout history. As you journey through the exhibits, your guide will provide insights into the culture and lifestyle of the city.

In the afternoon, take the elevator up to the Kuchu Teien Observatory on the rooftop of the Umeda Sky Building, a landmark duo of 40-story towers linked by an atrium-like walkway. After taking in the view, head to the vibrant and historic Shinsaibashi Shopping District, a long arcade filled with shops selling everything from kimonos to jewelry. Then, end the day in the lively Dotonbori, the city's go-to area for entertainment.

Day 3: Train to Kyoto, Explore Fushimi Inari-Taisha Shrine & Tofuku-ji Temple

The 10,000 Red Gates of Fushimi Inari
Hike through the famous 10,000 red torii gates at Fushimi Inari-Taisha

Make your way to Osaka's station to catch the half-hour bullet train to Kyoto, Japan's cultural capital. Kyoto is alive with history and is home to numerous shrines, temples, palaces, and gardens. Once you've arrived, check into your hotel, put on comfortable shoes, and then join a three-hour guided tour, starting with an enchanting morning hike at the famous Fushimi Inari-taisha shrine.

Walk through the 10,000 red torii gates and follow the torii-lined route up to the observation deck atop the mountain for panoramic views of the gates and the surrounding forest. Walk back through the forest, discovering smaller shrines, moss-covered animal statues, and ancient stone tablets before reaching the historic Tofuku-ji Temple.

Inside, see the Hondo (main hall), with a beautiful seated Buddha statue and intricately carved wooden ceilings. Another highlight is the Tsutenkyo Bridge, a picturesque covered walkway that connects to the Kaizando Hall. Then, make your way to the many sub-temples within the complex, including the Reiun-In, featuring a traditional Japanese rock garden, and the Ryogin-an, known for its courtyard teahouse. Afterward, spend your afternoon relaxing at your hotel or venture out for lunch and some shopping. 

Day 4: Temple & Castle Tour, Kimono Tea Ceremony & Samurai Museum

Geisha in Gion District
Step back in time as you walk through Kyoto's historic Gion District

After breakfast, spend the morning exploring more of Kyoto's fantastic sights with your guide. Begin at the UNESCO-listed Kinkaku-ji, the Golden Pavilion. Stroll through the gardens and marvel at the gold-leaf-covered structure reflected in the surrounding ponds, then continue to another UNESCO World Heritage site, Nijo Castle, home to the Edo period's first shogun (military leader). As you explore the castle grounds, your guide will provide insights into the architectural grandeur and lavish decor of the Ninomaru Palace.

Your next stop is Gion, Kyoto's famous geisha district, where you'll have free time to roam. Wander down the stone street of Hanami-koji, bordered by traditional wooden townhouses and shops, and see if you can spot the beautiful geishas on their way to appointments. At the corner of Shijo Street and Hanami-koji, you'll find the legendary Ichiriki Ochaya Teahouse, the 300-year-old establishment that is invite-only but still makes for an iconic photo.

Refresh at your hotel before this afternoon's tea ceremony at Kyoto Maikoya. When you arrive, change into a kimono and learn about the ceremony, called sado or chanoyu. Sit down on a tatami mat and join in the ritual of matcha led by a knowledgeable tea master. After the ceremony, walk to the Samurai Ninja Museum to learn about these legendary warriors. Browse the collection of authentic samurai artifacts to gain insight into the lives of the samurai and ninja. 

Day 5: Day Trip to Nara & Uji

Meet the friendly deer in Nara Park
Plan your trip to Japan
Chat with a local specialist who can help organize your trip.

This morning, you'll take a one-hour train ride to Nara, a quaint city renowned for its picturesque parks, ancient temples, and free-roaming deer. Meet your guide and set off on a full-day tour of the town, starting at Kofuku-ji, a Buddhist temple built in 669 CE. Admire the five-storied pagoda, offering a glimpse into the Nara architectural style, and explore the sprawling temple complex encompassing multiple halls and structures.

Continue to Nara Park to discover another Buddhist temple, Todai-ji. Constructed in 752 CE, this is one of Japan's most historically significant temples, known for the giant bronze Buddha statue sitting in the main hall. Visit the UNESCO-listed Kasuga-Taisha next, an intricately detailed Shinto shrine surrounded by the Kasugayama Primeval Forest. As you walk through the grounds, look out for the playful deer, who bow in exchange for food, then stop for saké at a local brewery. 

On the return train journey from Nara, stop at the charming city of Uji to explore the Byodo-in Temple, a Buddhist structure known for its traditional stores offering green tea products (including the famous green tea ice cream). Finish your visit in the Byodo-in Omotesando neighborhood, the best place for dinner and souvenir shopping, before returning to Kyoto.

Day 6: Train to Magome, Nakasendo Trail (Day 1): Magome to Tsumago

The Nakasendo Trail near Tsumago.
Begin your epic trek on the Nakasendo Trail in the picturesque post town of Magome

Wake up early today to catch a two-hour bullet train to Nakasugawa, where you'll board a 30-minute bus to the village of Magome, whose charming streets are lined with wooden buildings. This post town (Edo-era rest stop) is the starting point for your five-day hike. From Magome, you'll walk for 5 miles (8 km) on one of the best-preserved portions of the famous Nakasendo Trail, one of five major routes of the Edo period, connecting Edo and Kyoto across more than 300 miles (482 km).

Trek along the trail over the Magome Pass to the exquisitely preserved town of Tsumago, a living museum that's home to residents whose families have lived here for generations. Wander the village streets, taking a step back in time as you take in the area's rugged beauty. Cars aren't allowed on the main roads here, and electrical wires are carefully concealed, adding to the old-world charm.

Visit Kotoku-ji, a temple dating from the 1500s with a singing floorboard, or stop in at the Waki-honjin Inn, once used by feudal lords. If you're not too tired and want to explore more, hike up to the ruins of Tsumago Castle. You'll spend tonight at a minshuku, or family-run inn, for a delicious home-cooked meal and well-deserved rest. After dinner, stroll through the village streets wearing the yukata (kimono-style robe) supplied by your inn.

Day 7: Nakasendo Trail (Day 2): Tsumago to Nojiri, Train to Kiso-Fukushima

Traditional Wooden Building in Tsumago, Japan
Hike along the Nakasendo Trail from the beautiful post town of Tsumago to Nojiri

The morning begins with what will be the longest hike of your trip, taking you along a beautiful section of trail from Tsumago to the post station of Nojiri. The 11.5-mile (17 km) path snakes through valleys and bamboo and cedar forests, offering some of the most unspoiled scenery of the trip. Since you'll pass through some steep sections during the moderate, six-hour trek, the shorter, one-hour hike to the village of Nagiso is also an option.

Whichever town you choose, Nojiri or Nagiso, head to the local train station, where you'll board a half-hour train bound for Kiso-Fukushima. There, you'll stay the night in a ryokan (traditional inn) set in a tranquil valley. The inn features indoor and outdoor hot spring baths for relaxing after your hike.

Day 8: Train to Yabuhara, Nakasendo Trail (Day 3): Yabuhara to Narai

Traditional gates at the top of the Torii Pass.
Take in the mountain air and serene forest views as you trek along the Nakasendo Trail

This morning, hop on the train for a quick 15-minute ride to the village of Yabuhara. From there, you'll go on a steep, uphill hike to the Torii Pass, which, at nearly 4,000 feet (1,197 m), is the highest point of the Nakasendo Trail. As you leave the village behind, the trail meanders through lush forests and tranquil landscapes, allowing you to immerse yourself in nature.

Along the way, stop at Ontake Shrine, dedicated to Mount Ontake, one of Japan's most revered volcanoes. Red cedar forest and ancient, moss-covered statues mark the highest point of the journey, where you'll start your descent to the atmospheric village of Narai. Today's 3.2-mile (5.3 km) hike ends here, the most well-preserved post town on the trail, which also marks the halfway point.

Walk along the town's cobbled streets to see the traditional wooden merchant houses and storefronts, then cross the Narai River over the arched Narai Kiso Bridge. After your day's exertions, settle into one of the town's cozy family-run inns for the evening. 

Day 9: Nakasendo Trail (Day 4): Narai to Kiso-Hirasawa, Train to Karuizawa

The picturesque post town of Narai.
Spend extra time exploring the picturesque post town of Narai

Today's hike takes you to Kiso-Hirasawa, an easy 2-mile (3.3 km) jaunt from Narai. Since the Edo Period, this town has been famous for its high-quality lacquerware, and you'll have time to visit some of the small shops. Then, board the one-hour train to Matsumoto for the famed 16th-century Matsumoto Castle. Admire the iconic black-and-white facade of "Crow Castle," then head inside to climb the steep wooden staircases to the top for panoramic city views.

After exploring the castle, continue by train to the town of Karuizawa, where you'll spend the final night of the trip. Check into a historic inn with a traditional Japanese bath before stepping out to see some of the local sights. Visit Fukushima Sekisho-ato, the old checkpoint with a museum attached, or the Kiso-Fukushima Historical Museum, which displays artifacts and an old farmhouse from Kida Village

Day 10: Nakasendo Trail (Day 5): Karuizawa to Yokokawa, Train to Tokyo

Welcoming locals along the Nakasendo Trail.
End your adventure along the Nakasendo Trail in Yokokawa before catching the train to Tokyo

The final stretch of the adventure leads you from Karuizawa to Yokokawa. Hike over the high plateaus of the Usui-toge Pass and rest at the Usui Pass Observation Platform, where you can rest and take in the sweeping view of verdant mountains after the 1.5-hour hike through the woods.

Climb a few more steps to the Kumano Shrine to enjoy a cup of tea and some Japanese sweets in one of the nearby tea houses. Once refreshed, continue on some of the most pristine parts of the trail, taking in the gorgeous mountain views as you gradually descend through the forest. You'll finish today's 10-mile (16.7 km) trek at Yokokawa Station and catch a 1.5-hour train to Tokyo, where you'll check into your hotel for a well-deserved rest.

Day 11: Best of Tokyo Tour

Meiji Shrine Tokyo
Explore the bright lights and ancient history of Japan's capital, Tokyo

Join your guide this morning for a full day exploring Tokyo's iconic landmarks, starting at the Meiji Jingu Shrine, built in 1920 CE. Step through the towering torii (gate) into the forested grounds and admire the ornate Japanese architecture. Continue your tour to the Tsukiji Outer Fish Market, a bustling hub with stalls offering seafood from sushi to grilled scallops. After the market, head to the Imperial Palace. Walk through the picturesque grounds, stopping at tea houses or bridges, including the famous double-arched Nijubashi Bridge.

Finally, visit Senso-ji, one of Tokyo's most significant Buddhist temples, built in the seventh century. Inside, stroll along the buzzing Nakamise-dori, lined with shops, until you reach the second gate, Hozomon, which leads to the temple's main hall and a five-story pagoda where you can pick up an omikuji (a Japanese fortune slip). At the end of your tour, return to your hotel and unwind.

Day 12: Day Trip to Mount Fuji with Lake Cruise & Whisky Tasting

best time to visit Japan - Chureito pagoda during Spring time, with Mount Fuji in background
See the iconic views of Mount Fuji from Arakurayama Sengen Park

Take a day trip from Tokyo today to the Fuji Five Lakes region to see the iconic Mount Fuji from different viewpoints. Meet your guide and travel for two hours to the famous Arakurayama Sengen Park. Ascend to the beautiful Chureito Pagoda perched on the hillside and surrounded by seasonal foliage, including cherry blossoms in spring. Enjoy panoramic views of the snowcapped mountain, then walk around the eight ponds of Oshino Hakkai, created by snowmelt from the slopes of Mount Fuji itself. 

In the afternoon, join your guide for a cruise on the picturesque lake Kawaguchi-ko. Pass charming lakeside villages with Mount Fuji as a backdrop reflected on the water. Or, savor the sights on the Mount Fuji Panoramic Ropeway. Hop off at the observation deck under Mount Tenjo, which provides incredible panoramas of Fuji and the surrounding area. Then, stop at the Fuji Gotemba Distillery, which distills malt and grain whiskies. Learn about the multiple stages of distilling and taste a glass of whisky before returning to Tokyo for your last night in Japan.

Day 13: Depart Tokyo

Enjoy one last sunrise over Tokyo before heading to the airport for your departing flight
Pack your bags and prepare to say goodbye to Japan as you meet your driver for transfer to the airport. Have a safe journey home or to your next destination!

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Map of Culture & Hiking in Japan: Osaka, Kyoto, Tokyo & the Nakasendo Trail - 13 Days
Map of Culture & Hiking in Japan: Osaka, Kyoto, Tokyo & the Nakasendo Trail - 13 Days