In the morning, you’ll meet your guide and leave Osaka by private vehicle, heading into the forested mountains of the Kii Peninsula to reach the sacred town of Koyasan. Founded over 1,200 years ago, Koyasan is a center of Shingon Buddhism and home to more than a hundred temples nestled among tranquil cedar groves. Today’s walk follows the Choishi Path (Choishi-michi), a historic pilgrimage trail once walked by countless devotees. Marked by stone stupas placed every 109 m (358 ft), the route links modern travelers with pilgrims of centuries past. As we ascend through moss-draped forests, the path evokes a deep sense of reverence and continuity. The walk ends at the crimson Daimon Gate, marking the entrance to Koyasan. We stay at Rengejoin Temple, where guests can join a meditation session and enjoy a traditional vegetarian dinner before an optional night walk through Okunoin Cemetery.

Meals: Lunch, dinner
Hiking: 8 km (5 mi), 4.5 hours
Elevation: +794 m (2,605 ft), -460 m (1,509 ft)
Terrain: Earthy paths, moss-covered stones, tree roots
Accommodation: Rengejoin Temple

Before breakfast, there’s another opportunity to join a morning meditation session. After a traditional Japanese vegetarian breakfast, we travel south by private vehicle to Takijiri-Oji (1.5 hours). The walk begins at this sacred gateway on the Kumano Kodo pilgrimage route. From here, we ascend through forested trails lined with mossy boulders and the Tainai-kuguri cave, a symbolic passage once used by pilgrims. The path continues toward Takahara Kumano-jinja shrine, shaded by ancient camphor trees. Reaching the village of Takahara, “Kiri-no-Sato” or “Village in the Mist,” offers sweeping views over the Hatenashi range. Those taking the shorter option finish here, while others continue through cedar forests, passing Oji shrines, terraced slopes, and the remains of Uwada-jaya Teahouse before a steep descent past the Three-Fold Moon Viewing point to Michi-no-Eki Gyuba-doji. We then transfer back to Takahara Organic Hotel for dinner featuring fresh, local ingredients and wine.

Meals: Breakfast, lunch, dinner
Hiking: 12 km (7.5 mi), 5–6 hours
Elevation: +830 m (2,723 ft), -640 m (2,100 ft)
Terrain: Steep and sustained ascents, forest trails, uneven surfaces
Accommodation: Takahara Organic Lodge

Flexible hiking option 1: 8.7 km (5.4 mi), 4.5 hours, +320 m (1,050 ft), -400 m (1,312 ft)
Flexible hiking option 2: 3.9 km (2.4 mi), 3 hours, +357 m (1,171 ft)

After breakfast, we transfer back to the trail to begin our walk from Gyuba-doji. The route climbs steadily toward Hashiori-toge Pass, where a striking statue of Emperor Kazan stands, symbolically riding both a horse and an ox—representing the spiritual duality of the pilgrimage. From this high point, we descend a beautifully preserved cobblestone staircase to a scenic viewpoint overlooking Chikatsuyu Village. Across the Hiki-gawa River lies Chikatsuyu-oji Shrine, steeped in local legend. The trail then ascends through peaceful forests toward Kobiro-oji, passing ancient waymarkers and gentle ridges before reaching Tsugizakura-oji, home to centuries-old cedars and the historic Toganoki-jaya teahouse site. In the afternoon, we transfer to Watarase Onsen, a renowned hot spring village. We check into Hotel Sasayuri for a three-night stay. Spacious rooms, open-air baths, and a beautifully prepared dinner featuring seasonal cuisine provide the perfect setting for relaxation after the day’s walk.

Meals: Breakfast, lunch, dinner
Hiking: 8 km (5 mi), 5 hours
Elevation: +115 m (377 ft), -100 m (328 ft)
Terrain: Earthy paths, tree roots, stone steps, cobblestones, steady climbs
Accommodation: Watase Onsen Hotel Sasayuri

Flexible hiking option: 5 km (3.1 mi), 2.5 hours, +115 m (377 ft)

Following a hearty breakfast, we begin our walk at Hosshinmon-oji, making our way toward Kumano Hongu Taisha through serene forests and quiet mountain villages. The trail reveals a series of breathtaking panoramic views, offering moments of reflection amid the sacred landscape. At Fushiogami-oji, we catch our first glimpse of the massive torii gate of Hongu Taisha, standing 33.9 m (111 ft) high. From here, the path gradually descends toward the shrine complex, where simplicity and elegance blend seamlessly with the surrounding forest. After exploring this spiritual heart of the Kumano Kodo, we return to our accommodation at Watarase Onsen Hotel Sasayuri. This evening, enjoy a traditional dinner highlighting regional flavors, served with wine in a peaceful riverside setting.

Meals: Breakfast, lunch, dinner
Hiking: 10 km (6.2 mi), shorter walk available today
Elevation: +100 m (328 ft)
Terrain: Earthy paths, tree roots, stone steps, cobblestones
Accommodation: Watase Onsen Hotel Sasayuri

After breakfast in the restaurant, we begin our walk from Ukegawa, ascending steadily toward Hyakken-gura. Along the way, we pass the remains of the Matsuhata-jaya Teahouse before reaching the top of Hyakken-gura, where a breathtaking panorama reveals the vast beauty of the surrounding landscape. From here, the path winds through tranquil forests, immersing us in a serene atmosphere of towering trees and filtered light. The trail then descends gradually toward the remote mountain village of Koguchi, a peaceful settlement nestled among rivers and peaks. Surrounded by pristine wilderness, Koguchi exudes a quiet charm that reflects the timeless spirit of the Kumano Kodo. After exploring, we transfer back to Hotel Sasayuri. This evening, enjoy a traditional dinner accompanied by wine, celebrating the flavors of the region.

Meals: Breakfast, lunch, dinner
Hiking: 13 km (8.1 mi), shorter walk available today
Elevation: +420 m (1,378 ft)
Terrain: Earthy paths, tree roots, stone steps, cobblestones
Accommodation: Watase Onsen Hotel Sasayuri

After breakfast, we make our way to Koguchi to begin our challenging walk toward the Grand Nachi Taisha Shrine. The trail climbs steeply through ancient forests and along ridgelines, passing remnants of terraced rice paddies and moss-covered stone walls. The ascent rewards walkers with sweeping mountain and ocean views from the summit, a fitting testament to the effort. The path then descends through serene woodland to the sacred grounds of Nachi Taisha, the Seiganto-ji Temple, and the awe-inspiring Nachi-no-Otaki Waterfall—Japan’s tallest, cascading 133 m (436 ft) in a single drop. Together, these sacred sites form a harmonious union of nature and spirituality. After the walk, we transfer to the coastal fishing village of Kii-Katsuura and check into Hotel Urashima, offering stunning bay views. This evening, enjoy an elaborate buffet dinner accompanied by wine.

Meals: Breakfast, lunch, dinner
Hiking: 14.5 km (9 mi), 8 hours
Elevation: +1,260 m (4,134 ft), -930 m (3,051 ft)
Terrain: Earthy paths, tree roots, stone steps, cobblestones, steep ascents and descents
Accommodation: Hotel Urashima, Kii-Katsuura

Flexible hike option: 5.5 km (3.4 mi) return walk from Nachi Taisha to Teahouse remains and back

We travel to the Kumano River to experience a traditional boat cruise. For over a century, pilgrims have journeyed to Kumano in wooden flat-bottom boats, following the sacred waterways toward the shrines. As we glide down the picturesque gorge, enjoy spectacular river views framed by lush cliffs and cascading waterfalls. Our boat arrives in Shingu, where we visit the Kumano Hayatama Taisha Grand Shrine, which has stood on this riverbank since at least the 12th century. This revered site forms part of the UNESCO World Heritage “Sacred Sites and Pilgrimage Routes in the Kii Mountain Range.” Afterwards, we travel by private vehicle back to Osaka and check into the hotel. Tonight, celebrate the journey with dinner and a toast of sake or beer shared with the group.

Meals: Breakfast, lunch, dinner
Accommodation: Aloft Hotel Osaka

After breakfast, we travel to Kyoto. After a brief stop at our hotel, we visit one of the city’s most iconic sites: the Fushimi Inari Shrine. Walking through its thousands of vivid orange torii gates is a mesmerizing experience, as the tunnel-like path winds through the forest and up the hillside. The walk is both visually stunning and deeply spiritual, culminating in sweeping views of Kyoto from the summit. Afterward, we enjoy lunch at a local restaurant featuring traditional Japanese cuisine. Returning to The Royal Park Hotel Kyoto Sanjo, there’s time to relax before our special afternoon experience—a Japanese tea ceremony. Dressed in exquisite kimonos (with hair styling for women), we learn the graceful art of tea preparation, a practice that fosters mindfulness and simplicity. This cultural highlight concludes with a group dinner at a local restaurant, accompanied by wine.

Meals: Breakfast, lunch, dinner
Hiking: 6 km (3.7 mi), 3 hours
Terrain: Stone paths, forest trails, hillside stairways
Accommodation: The Royal Park Hotel Kyoto Sanjo

After breakfast at the hotel, we transfer by private vehicle from Kyoto to Hosokute-juku, a tranquil and lesser-visited post town along the Nakasendō Trail. Today’s walk takes us from Hosokute-juku to Okute-juku, one of the most beautifully preserved and scenic stretches of the route. The trail winds through quiet forest, historic stone-paved paths, and gently rolling countryside, offering an authentic experience of rural Japan. Along the way, we pass moss-covered waymarkers, serene shrines, and traditional thatched-roof farmhouses that reflect centuries of travel along this ancient road. As we near Okute-juku, the landscape opens to views of surrounding hills and farmland, showcasing the natural beauty of the Gifu region. At the end of the walk, we meet our private vehicle and continue to Ena for a hands-on Hiroshige ukiyo-e woodblock printmaking workshop. Later, we check into Enakyo Onsen Hotel Yurisha and enjoy dinner with wine.

Meals: Breakfast, lunch, dinner
Hiking: 11 km (6.8 mi), 4 hours
Elevation: +450 m (1,476 ft), -480 m (1,575 ft)
Terrain: Forest trails, stone paths, undulating hills
Accommodation: Enakyo Onsen Hotel Yurisha

After an enjoyable breakfast, we begin today’s journey with a scenic walk to the beautifully preserved post town of Magome. We stroll through its cobblestone streets, passing wooden watermills and traditional houses that embody Edo-era Japan. From Magome, the trail ascends gradually toward the serene Magome Pass. As we climb, the scenery shifts from open countryside to the tranquil forests of the Kiso Valley. Midway, we pause at a traditional Japanese home, where hosts in period attire serve warm tea beside an irori hearth—a charming glimpse into local culture. Reenergized, we continue through lush woodland, passing a pair of picturesque waterfalls before reaching the timeless village of Tsumago. Nestled among forested hills and flowing rivers, Tsumago offers an authentic window into rural Japan. After exploring, we transfer and we’ll unwind in the onsen before a multi-course dinner with sake or beer.

Meals: Breakfast, lunch, dinner
Hiking: 10 km (6.2 mi) or 5 km (3.1 mi), 4 hours
Elevation: +461 m (1,512 ft)
Terrain: Forest and countryside trails, stone paths, asphalt sections
Accommodation: Kisjo Hotel Tsumago

After breakfast, we farewell our accommodation and transfer to Nagiso to begin today’s walk. The trail follows the Yogawamichi Path from Modono to Nojiri, a scenic route that avoids the busy riverside road. This captivating walk meanders through unspoiled countryside, serene alpine forests, and traditional mountain villages, offering an authentic glimpse into rural life in the Kiso Valley. As we ascend through dense cedar forests, filtered light reveals glimpses of distant peaks and valleys below. The path combines natural beauty with cultural depth, embodying the quiet spirit of Japan’s ancient travel routes. After the walk, we meet our driver and continue to the charming town of Kiso-Fukushima. In the early evening, there’s an optional visit to a local sake brewery to meet the friendly staff and sample regional varieties before enjoying a traditional dinner with sake or beer.

Meals: Breakfast, lunch, dinner
Hiking: 13 km (8.1 mi) or 10 km (6.2 mi), 4 hours
Elevation: +669 m (2,195 ft)
Terrain: Steep sections, stone paths, wooden footbridges, dirt trails
Accommodation: Tsutaya Inn, Kiso Fukushima

After breakfast, we travel through the mountainous landscapes of southeast Nagano, transferring to the base of Mt. Ontake to begin today’s walk. This trail—often described as one of Japan’s most captivating—begins with a steep stone staircase ascending through dense forest to the monument of the Three Great Gods of Ontake, known as Omata Sansha. The path continues through lush woodland, passing sacred Reijinhi stone carvings used in ancient rituals. Along the way, we visit Hanadofukando and Juni Gongen Shrines before reaching Shintaki Falls, a 50 m (164 ft) cascade revered for its purification ceremonies. Pilgrims have long journeyed here to cleanse both body and spirit. The final stretch leads to Kiyotaki Falls, another sacred site framed by mossy rocks and serene forest. After the walk, we transfer to Tsutaya Tokinoyado Retreat to relax in the open-air onsen before a delicious dinner with sake or beer.

Meals: Breakfast, lunch, dinner
Hiking: 6 km (3.7 mi), 4–5 hours
Elevation: +250 m (820 ft), -250 m (820 ft)
Terrain: Stone paths, steep staircases, dirt forest trails
Accommodation: Tsutaya Tokinoyado Retreat

Flexible hike option: 4–5 km (2.5–3.1 mi), 3 hours, +150 m (492 ft); gentle inclines, minimal stairs

After breakfast, enjoy the views of Mt. Ontake before setting out on today’s walk. The journey from Yabuhara to Narai via Torii Pass feels like stepping back in time through the heart of the Kiso Valley. The trail winds through tranquil forests where sunlight filters through the canopy, occasionally revealing wooden torii gates marking progress toward the pass. As we ascend, the scenery opens to sweeping views of the Kiso Valley, dotted with traditional villages nestled among the mountains. Arriving in Narai, a beautifully preserved post town, we’re greeted by cobblestone streets, Edo-era architecture, and the timeless charm of old Japan. After the walk, enjoy time to explore Narai at your own pace before continuing to the picturesque town of Karuizawa. Our accommodation tonight is at the elegant Ancient Hotel, a luxurious woodland retreat with soothing hot springs. Dinner is served with sake or beer.

Meals: Breakfast, lunch, dinner
Hiking: 7 km (4.3 mi)
Elevation: +373 m (1,224 ft)
Terrain: Forest trails, stone paths, dirt tracks, moderate inclines
Accommodation: Ancient Hotel, Karuizawa

Flexible option: Transfer directly to Narai and spend the day at leisure

After a satisfying breakfast at the Ancient Hotel Karuizawa, we begin our final day of walking with a peaceful forest trail that descends gently through cypress-lined woodland. Our first stop is the secluded Ryugaeshi Falls, a hidden gem surrounded by moss-covered stones and rich greenery. Continuing along shaded paths, we reach Shiraito Falls, one of Japan’s most beautiful waterfalls. Stretching 70 m (230 ft) wide and 3 m (10 ft) high, its delicate streams cascade over the rock face like white silk, creating a tranquil atmosphere for reflection. After a short break, we travel to the historic Usui Pass to begin our second walk of the day. Starting from the Usui Pass Observation Deck with sweeping views of Mt. Asama, we follow an old Nakasendō trail to Kumano Kotai Shrine before descending through quiet forest to Karuizawa Old Town. Later, we return to Tokyo, concluding our remarkable journey.

Meals: Breakfast, lunch
Hiking: 6.5 km (4 mi), 3.5 hours
Elevation: -320 m (1,050 ft)
Terrain: Cypress-lined forest trails, stone paths, dirt tracks, steep descents

Flexible hike option: 2.5 km (1.6 mi), 1–2.5 hours, Ryugaeshi Falls to Shiraito Waterfall; or short Shiraito Waterfall walk, 30 minutes