We’ll meet in the foyer of Hotel Metropolitan Tokyo Marunouchi at 8am. From there, we make our way to the town of Yokokawa, where our walk begins just 1 km outside of town at the Usui trailhead. The trail gradually ascends as we enjoy scenic views and countless stone relics, eventually reaching the picturesque Usui Pass. At this idyllic spot, we’ll take a break—exploring the Kumanokotai Shrine or treating ourselves to a delicious ice cream at the nearby café, all while savoring panoramic views of the majestic Mt. Asama. Next, we’ll continue to the Observation Deck for even more stunning mountain vistas. Afterwards, we’ll head to our fabulous accommodation for the night: the charming Ancient Hotel in Karuizawa. Tonight, we’ll enjoy a well-earned dinner served with wine.

Meals: Breakfast, lunch
Hiking: 8 km (5 mi), 4.5 hours

This morning, we’ll enjoy breakfast before taking a short detour to visit the stunning Shiraito Waterfall, tucked away in a serene forest. Measuring three meters high and 70 meters wide, it’s often considered Japan’s most beautiful waterfall. Shiraito no Taki means “the waterfall of white threads,” a name that perfectly captures the sight of countless delicate streams cascading down the rock face like a white curtain. After soaking in this natural wonder, we’ll transfer to Yabuhara and begin our walk for the day.

Today’s hike takes us on a picturesque journey from Yabuhara to Narai via the historic Torii Pass—a walk through the heart of Japan’s Kiso Valley that feels like a step back in time. The trail winds through peaceful forests, where sunlight filters through a green canopy and wooden torii gates appear mysteriously amid the trees. As we ascend, the landscape opens up to sweeping views of the Kiso Valley, dotted with traditional villages cradled by the mountains. Arriving in Narai, a beautifully preserved Edo-period post town, we’ll stroll its cobblestone streets and soak in the timeless atmosphere. After some free time to explore, we’ll head to the scenic Kaida Plateau. Our accommodation tonight is the superb Tsutaya Tokinoyado Retreat, which overlooks the majestic Mount Ontake. Dinner will be served at the hotel’s restaurant, complete with wine.

Meals: Breakfast, lunch, dinner
Hiking: 9 km (5.6 mi)
Elevation gain: 373 m (1,223 ft)
Accommodation: Tsutaya Tokinoyado Retreat

After breakfast, we journey through the mountainous landscapes of southeastern Nagano, transferring to the base of the impressive Mt. Ontake—the starting point of today’s walk. This trail is the owner’s personal favorite in all of Japan, and one you truly shouldn’t miss. We begin with a steep stone staircase winding through the forest, leading us to the Omata Sansha, the monument of the Three Great Gods of Ontake. From there, we continue through lush woodlands, passing numerous Reijinhi—sacred stone carvings used in Ontake’s mountain pilgrimage rituals.

Along the way, we visit Hanadofukando and the Juni Gongen Shrine, both steeped in spiritual tradition, before reaching the dramatic Shintaki Falls. Cascading down 50 meters, these falls—like many others around Ontake—are revered for their use in purification rituals. People travel from afar to experience their cleansing powers. As we near the end of this rewarding journey, we pause for lunch before arriving at our final highlight: Kiyotaki Falls, another breathtaking site of spiritual cleansing. After the walk, we return to the superb Tsutaya Tokinoyado Retreat. Soak in the open-air onsen hot springs before gathering for dinner in the restaurant, served with sake or beer.

Meals: Breakfast, lunch, dinner
Hiking: 6 km (3.7 mi), 4.5 hours
Elevation gain: 323 m (1,059 ft)
Accommodation: Tsutaya Tokinoyado Retreat

After breakfast, we bid farewell to our accommodation and make our way to Nojiri, where today’s walk begins. Rather than following the busy riverside road, we take the quieter Yogawamichi Path from Nojiri to Modono. This captivating route winds through Japan’s lush and untouched countryside, offering a peaceful journey across alpine landscapes, forested hills, and charming rural villages—providing a true glimpse into traditional life in the Kiso Valley. As we walk through dense cedar forests in all their natural beauty, we’re treated to occasional views of distant mountain peaks through the trees.

At the end of the trail, our driver meets us for a scenic transfer to the historic town of Tsumago. Tonight, we’ll enjoy a traditional Japanese dinner, served with wine, at the lovely Maruya Inn.

Meals: Breakfast, lunch, dinner
Hiking: 13 km (8 mi), 4 hours
Elevation gain: 669 m (2,194 ft)
Accommodation: Maruya Inn

After an enjoyable breakfast, we set out on our walk toward the old post town of Tsumago—a time-honored jewel nestled in Japan’s lush Kiso Valley. Tsumago enchants with its meticulously preserved Edo-era architecture, evoking the sense of stepping into a living museum. Surrounded by scenic mountains and a winding river, its tranquil atmosphere invites us to experience the serene beauty of rural Japan in its most authentic form.

Today’s walk takes us from Tsumago to Magome, along a scenic trail where we pass a pair of captivating waterfalls and watch the landscape shift from wide countryside views to the dense, green embrace of the Kiso Valley. Along the way, we stop at a traditional-style Japanese house where staff in period dress serve us tea beside an iron fire pit—a warm and memorable rest. Our path then ascends toward the enchanting Magome Pass, before eventually descending into the cobblestone streets of Magome itself. With its wooden watermills and well-preserved Edo-era architecture, this quaint town radiates timeless charm. After time to explore, we visit the Naegi Castle Ruins—often likened to Peru’s Machu Picchu for their cliffside setting and ancient mystique. Later, we head to our accommodation for the night: the charming Ichikawa Inn, a 400-year-old guesthouse still run by the owner’s sixth-generation family. Tonight, enjoy a lovingly prepared organic dinner, made from recipes passed down through the generations.

Meals: Breakfast, lunch, dinner
Hiking: 10 km (6.2 mi), 4 hours
Elevation gain: 461 m (1,512 ft)
Accommodation: Ichikawa Inn

After breakfast, we set out on today’s walk from Okute-juku to Oi-juku—a journey through time and tradition in the heart of rural Japan. Leaving the quaint post town of Okute-juku, with its beautifully preserved Edo-period buildings and cobblestone streets, we follow a peaceful path through lush countryside. Along the way, we pass traditional thatched-roof farmhouses, vibrant rice paddies, and gently flowing streams. The route offers tranquil shrines and quiet rest stops where we can pause and take in the calm rhythm of rural life in Japan.

In the afternoon, we return to our accommodation and enjoy a leisurely stroll to the nearby Hiroshige Museum of Art—a cultural haven celebrating traditional Japanese woodblock art. Here, we’ll have the chance to try our hand at creating our own masterpiece, offering a hands-on connection to Japan’s rich artistic legacy. We return for the evening to our welcoming inn, where we’ll enjoy a delicious dinner made from organic recipes passed down through generations—served with warm Japanese hospitality.

Meals: Breakfast, lunch, dinner
Hiking: 14 km (8.7 mi)
Accommodation: Ichikawa Inn in Ena

This morning, after breakfast at the hotel, we transfer by private vehicle to Hikone, a captivating castle town nestled along the peaceful shores of Lake Biwa. As we wander through its historic streets, we uncover fascinating stories from Japan’s feudal era. Hikone remains a hidden gem, with its castle proudly holding the status of a Japanese National Treasure. The town’s charm has even made it a backdrop for numerous period films, including the acclaimed “Shogun” starring Richard Chamberlain and Toshiro Mifune.

Later, we travel to Kyoto and check in at The Royal Park Hotel Kyoto Sanjo. After some free time, we gather for a special afternoon experience: a traditional Japanese tea ceremony. Dressed in vibrant, exquisite kimonos of your choice—and for the women, with flowers styled in your hair—you’ll join our expert to learn this timeless ritual that encourages mindfulness and celebrates simplicity and humility. This memorable experience also offers fantastic photo opportunities. Tonight, the group comes together for a fabulous dinner in Kyoto, accompanied by fine wine.

Meals: Breakfast, lunch, dinner
Hiking: 3-6 km (1.8-3.7 mi)
Accommodation: Ichikawa Inn

This morning, we take on the final walk of our journey: the iconic Fushimi Inari Shrine trail, a must-see experience in Kyoto. Wander beneath thousands of vivid orange torii gates that form a mesmerizing tunnel, winding through the forest and ascending the hillside. This walk is as visually stunning as it is deeply spiritual, culminating in breathtaking panoramic views of Kyoto from the summit.

Afterwards, we enjoy a delicious lunch at a local restaurant serving traditional Japanese cuisine. We then return to the hotel, where our wonderful tour concludes around 3pm.

Meals: Breakfast, lunch
Hiking: 6 km (3.7 mi), 3 hours