This 4-day plan covers three of my favorite spots in Nagano Prefecture—each with its own charm, story, and unforgettable moments.
Day 1 – Discover the charming town of Obuse, famous for chestnut sweets and museums—but also full of calm, quiet streets and hidden gardens that feel like something out of a dream.
Day 2 & 3 – Explore central Nagano. Most people rush straight to Zenkoji Temple, but there’s so much more if you slow down. From a Seven Lucky Gods pilgrimage (my most favourite part) through peaceful neighborhoods to atmospheric alleys, antique shops, and delicious spots to eat—it’s a surprisingly rich area to wander.
To be honest, I wasn’t even planning to make an itinerary for this part of Nagano at first. I’ve been here countless times and thought I’d seen everything. But after doing a deep dive and researching every little corner, it became one of my all-time favorite routes. Even if you’ve already visited the area, I really recommend giving it another shot with this guide in hand.
Day 4 – Wrap up the trip in Matsumoto—a castle town with nostalgic streets, great food, and my personal favorite castle in Japan. You’ll finish the day with a short ride to a nearby onsen town for a well-earned soak, with an option for tattoo-friendly hot spring.
And of course, if you’ve been following me for a while, you already know—these itineraries are packed with cozy cafés and restaurants I’ve actually been to and loved.
Note: You might notice that this itinerary doesn’t include popular spots like the Jigokudani Monkey Park or Togakushi Shrine. That’s not because I don’t recommend them—quite the opposite. Both are absolutely worth visiting, but they’re more of a standalone experience and can easily take up most of your day.
These places are also pretty straightforward to explore: you head out, walk through beautiful natural surroundings, enjoy the visit, and return. That simplicity makes them a bit different from the more intricate walking routes I usually focus on.
Another major reason I decided not to include them is that my itineraries are designed to work in any season. With the monkey park, the chances of actually seeing monkeys during the green season are lower, as they tend to stay deeper in the forest. And while Togakushi is stunning in winter, its trails can be icy and slippery, which might not be ideal for everyone. So while these places are wonderful, they just don’t quite fit the flexible, all-season format of the rest of my guides.
All of the locations are accessible by public transport.
Itineraries are designed to be enjoyable in any season
I’ve listed the cities in the order I recommend exploring them, but these day trips aren’t directly connected and can be done in any sequence—except for central Nagano, which takes two days. While following the suggested order is ideal, it’s not essential. For example, you might choose to do them in reverse (Matsumoto > Nagano > Obuse), especially if you’re passing near Matsumoto on your way to Nagano and want to avoid backtracking.
