Timeless Japan

DAY 1 | SUN 08 NOV | ARRIVE TOKYO | 3 NIGHTS

Arrival into Tokyo marks the beginning of your journey into Japan’s layered past and present. After clearing customs and immigration, those who have arranged transfers are met by a local assistant and driven privately into the city. The hotel sits in Ginza, Tokyo’s most refined district, where contemporary architecture, department stores, galleries and restaurants sit side by side with long-established traditions.

With arrivals spread throughout the afternoon and evening, this first day is intentionally gentle. Time is yours to rest after the flight, take a quiet stroll through Ginza’s illuminated streets, or simply settle in and adjust to the rhythm of the city. Tomorrow, the journey truly begins.

Accommodation: Millennium Mitsui Garden Hotel Ginza

DAY 2 | MON 09 NOV | TOKYO

Today is about understanding Tokyo from the ground up, moving through the city as locals do, on foot and by rail. Over breakfast, the group gathers for introductions and a briefing on the journey ahead before heading out into the city.

The morning begins at the Nezu Museum, a masterwork of contemporary Japanese architecture by Kengo Kuma. The museum’s understated lines, natural materials and serene garden walkways create a seamless dialogue between art, architecture and landscape. Inside, a carefully curated collection of pre-modern Japanese and East Asian art provides cultural context for much of what lies ahead on the journey.

From here, wander through Aoyama, one of Tokyo’s most stylish neighbourhoods, arriving at Spiral, an iconic cultural complex where architecture, design, exhibitions and retail blur together. The afternoon sees a return to the hotel, leaving the evening free to explore Tokyo at your own pace, perhaps with dinner in Ginza or a quiet drink nearby.

DAY 3 | TUE 10 NOV | TO MATSUMOTO | 1 NIGHT

This morning, luggage is forwarded ahead to Takayama, allowing you to travel lightly into the Japanese Alps with just an overnight bag. After breakfast, transfer to the station and board the Shinkansen, enjoying a beautifully prepared bento box lunch as landscapes transition from dense city to mountain foothills.

Matsumoto sits beneath the dramatic peaks of the Alps and is best known for its striking original castle. One of only twelve remaining feudal castles in Japan, Matsumoto Castle’s black exterior has earned it the nickname “The Crow.” Exploring its grounds and interiors offers a tangible connection to Japan’s samurai era.

The afternoon also introduces a contrasting cultural layer with a visit to the Matsumoto City Museum of Art, home to works by Yayoi Kusama, whose international fame belies her deep connection to this small alpine city.

Check in to Matsumoto Jujo, a beautifully reimagined ryokan with roots dating back to 1686. The property blends onsen culture, literature, local produce and contemporary design, offering private open-air baths in each room. Dinner is a highlight, tracing ingredients from mountain headwaters to the Sea of Japan, before a deeply restorative night’s rest.

Accommodation: – Matsumoto Jujo, Asama Onsen – 1 Night
Meals: – Breakfast, bento lunch, dinner

DAY 4 | WED 11 NOV | TO TAKAYAMA | 2 NIGHTS

After breakfast, enjoy a relaxed walk through Matsumoto’s historic streets, including Nawate-dori and Nakamachi-dori, where traditional kura storehouses now house cafés, craft shops and galleries. The pace is unhurried, allowing time to browse handmade ceramics, lacquerware and woodwork.

Leaving the city, travel through the Azumino countryside to Daio Wasabi Farm, one of Japan’s largest producers of real wasabi. Here, learn about the delicate cultivation process and discover a more nuanced flavour profile than its Western counterpart.

The journey continues deeper into the mountains to Takayama, a town celebrated for its remarkably preserved Edo-period old quarter. On arrival, check in to a traditional ryokan, where tatami floors, futon bedding and hot spring baths offer a deeply Japanese experience. The evening is free to wander Takayama’s lantern-lit streets or relax in the baths.

Accommodation: – Oyado Koto No Yume – 2 Nights
Meals: – Breakfast, lunch, 1 x dinner

DAY 5 | THU 12 NOV | TAKAYAMA

Today brings Takayama’s living traditions into focus. A guided walking tour explores the Miyagawa Morning Market, historic government buildings, and beautifully preserved merchant streets where craftsmanship remains central to daily life.

Visits to the Yoshijima Heritage House and Kusakabe Folk Museum reveal the architectural ingenuity and social structures of wealthy Edo-period merchants, while sakabayashi cedar balls hanging under eaves quietly signal sake-making traditions still in practice.

After lunch, step inside a local sake brewery to learn about regional brewing styles before enjoying free time to explore independently. The evening culminates with dinner at a Japanese restaurant designated as a tangible cultural property, where cuisine and setting combine to evoke Takayama’s past.