Japan captured my heart the moment I arrived. It’s a country of stunning beauty, seamless travel, and endless comfort. Over two weeks, my partner and I explored the vibrant cities of Tokyo and Kyoto, but also ventured off the beaten path to experience Japan’s mountains and beaches. A highlight of the trip was walking a section of the Nakasendo, an ancient trading route between Kyoto and Tokyo. This historic trail, once traveled by royalty and their samurai entourages, remains beautifully preserved. Let’s dive into this unforgettable adventure.
In this blog, I’ll share the trip’s highlights, delve into specific areas, offer route recommendations, and break down the budget, so you can plan your own adventure. A summary of the itinerary is at the end!
Our Route
I love how in this trip, we were able to experience both legendary metropolis and quiet backcountry. Japan is such a diverse and beautiful country.
Our Itinerary Summary (2 weeks)
Day 1: Arrival in Tokyo
- Pro tip: Pick up a Wi-Fi router at the airport. Take the train into the city.
- We loved this hotel near Senso-ji Temple, Asakusa.
Day 2: Exploring Tokyo
- An early morning visit to Kaminarimon Gate and Senso-ji Temple will help doge the crowds!
- Stroll through cherry blossom-lined streets along the Sumida River.
- Visit Tokyo Skytree for panoramic city views.
- Walk through parks, a thrift market, and along cherry-blossom lined Oyoko River.
- Visit the Museum of Contemporary Art.
- Dinner at a sushi bar along the river.
Day 3: Ueno Park and Meiji Shrine
- Visit Ueno Park and explore temples and serene lakes.
- We loved this nearby vegan ramen restaurant.
- Visit Meiji Shrine and walk through its forested grounds.
- Explore Shibuya, ending the day with a tofu feast.
Days 4–6: Matsumoto and the Japanese Alps
- Day 4:
- Train to Matsumoto.
- Stay at a traditional ryokan near Matsumoto Castle.
- Visit Matsumoto Castle and enjoy soba noodles for dinner.
- Attend the Sakura night illumination at the castle.
- Days 5–6:
- Take the train to Narai and spend the day exploring the vibrant streets.
- Continue by train to Kiso-Fukushima and stay in onsen hotel.
- Soak in the ryokan’s onsen and enjoy multi-course meals.
- Take day trips by train to hike portions of the famous Nakasendo trail.
Days 7–9: Kyoto
- Day 7:
- Train to Kyoto. We stayed here (great private cedar baths in the rooms!)
- Visit Kyoto National Museum and Sanjusangendo Temple.
- Walk through Gion, explore temples, and enjoy sushi by the river.
- Day 8:
- Visit a traditional tea house.
- Tour Kyoto Imperial Palace with an audio guide.
- Visit Kinkaku-ji (Golden Pavilion).
- Walk along the Philosopher’s Path and enjoy dinner.
- Day 9:
- Rainy rest day exploring a local mall with umbrellas.
- Lunch at a tofu restaurant in the train station.
- Shop for gifts and mochi to take home.
Days 10–11: Izu Peninsula
- Day 10:
- Travel to Izu Peninsula via train from Kyoto (get off at Shizuoka, and take short local train a few stops to Shimizu Station) and take the local ferry (free bus from train station).
- Stay at a ryokan with ocean views and onsens.
- Hike the neighboring hills and walk along the beach.
- Day 11:
- Celebrate the day by hiking scenic trails and exploring small towns.
- Lunch at a sashimi restaurant.
- Walk along a canal and visit a free local museum.
- End the day with a buffet, strawberry cream cake, and an ocean-view soak.
Days 12-14: Tokyo Finale
- Day 12: Return to Tokyo.
- Stay in Koenji, a lively neighborhood known for its music and nightlife. We stayed here (in the two-bedroom villa option).
- Day 13:
- Visit the Imperial Palace and its gardens.
- Explore a historic museum and typography museum.
- Enjoy a bento box lunch in the Imperial Gardens.
- End the day at the Tokyo TeamLab immersive exhibit and with vegan ramen.
Now let’s dive in!
Tokyo: A City of Contrasts
Day 1: Arrival and First Impressions
We arrived in Tokyo and navigated to our stay near the Senso-ji Temple in Asakusa. After settling into our hotel, we explored the bustling streets lined with charming street-side eateries. I was immediately struck by the city’s energy and the sociable atmosphere.
Pro tip: One of our first steps was renting a Wi-Fi hotspot at the airport, which we reserved in advance! It was an invaluable tool for navigating the metro and finding our way.
Day 2: Early Morning Serenity and Cherry Blossoms
We started our day at 6:30 AM, heading to the iconic Kaminarimon Gate at Senso-ji Temple. Surprisingly, it was nearly empty—a rare treat in such a popular spot. From there, we wandered through serene, cherry blossom-lined streets and along the Sumida River, soaking in the tranquil beauty of the city.
Our morning walk led us to a 7-Eleven, where we enjoyed delicious onigiri and soft-boiled eggs before heading to the Tokyo Skytree. The panoramic views from the top were breathtaking, and on a clear day, you can even see Mount Fuji.
The rest of the day unfolded naturally, taking us to a vibrant thrift market, cherry blossom-filled parks, and local family playgrounds. After a long but delightful day of nearly 20,000 steps, we ended with a sushi feast before strolling back to the hotel along the river.
Day 3: Exploring Ueno Park and Meiji Shrine
We began our second full day in Tokyo at Ueno Park, grabbing breakfast from the amazing newly discovered 7-Eleven (rice onigiri and convenient store coffee surprisingly became a morning staple on our trip). The park was a haven of cherry blossoms, serene ponds, and charming animal-themed boats.
From there, we made our way to Meiji Shrine, a tranquil retreat in the heart of the city. Walking through its towering forest felt like stepping into another world. The contrast between the bustling city streets and the peaceful shrine was remarkable.
Following the Shrine, we explored the neighboring neighborhood of Harajuku which is a fun hipster and cool neighborhood in Tokyo, full of incredible aestetic coffee shops and winding tiny walking paths. We spent hours walking and browsing little thrift stores. It was a joy to take in all the street fashion as we walked. We even stopped at an “otter cafe” where guests can interact with otters. We wrapped up the day in Shibuya, enjoying a flavorful tofu feast (and one of our favorite meals).
Matsumoto and the Japanese Alps
Day 4: After soaking in the energy of Tokyo, we ventured to Matsumoto, a gateway to the Japanese Alps. The train journey offered stunning views of Mount Fuji and lush mountain landscapes.
Our hotel, just a short walk from Matsumoto Station, had a cozy communal vibe with a library and sauna. For only $40 a night, it was one of our most affordable yet memorable stays. I loved experiencing traditional Japanese stays. I thought it was so interesting how you have your mats to roll out each night, but can use the open space for tea during the day.
The highlight here was Matsumoto Castle, a 400-year-old marvel. Its intricate wooden interiors and panoramic views from the top were captivating. We also explored the local food scene, indulging in steaming bowls of soba noodles and tempura—a regional specialty.
In the evening, the castle’s night illumination cast a magical glow on the surrounding cherry blossoms, a sight I’ll never forget.
Hiking parts of the Nakasendo Trail
A lifelong dream of mine was to hike the Nakasendo trail, and it exceeded all expectations. This ancient route through the Kiso Mountains offered a peaceful escape, with bamboo forests, cedar groves, and cascading cherry blossoms guiding our way.
Day 5: Entering the Mountains
We started in Narai, which we reached by train. Narai is a beautifully preserved post town with traditional wooden architecture. After exploring its quiet streets for most of the day and indulging in another delicious soba meal, we made our way to Kiso-Fukushima. Our ryokan here was a haven of relaxation, complete with both indoor and outdoor onsen baths and an exquisite 11-course meal featuring local delicacies.
Day 6: Hiking the Nakasendo
From Kiso-Fukushima, we took day trips to hike sections of the Nakasendo, including the picturesque Magome to Tsumago trail. The journey was a feast for the senses, with colorful towns, old growth cedar forests, bamboo trails, serene waterfalls, and vibrant flower groves along the way.
Pro-tip: Collect stamps along the way! Every train station and major monument has stamps that are free to the public to use.
Kyoto
After an unforgettable time along the Nakasendo, we traveled to Kyoto, a city where tradition and tranquility meet. With its historic temples, peaceful gardens, and rich cultural heritage, Kyoto offered a slower, more reflective pace to our journey. Here’s how we spent our time in this enchanting city.
Day 7: Arrival and Afternoon Wanderings
Our morning began with a final soak in the onsen at our ryokan—a ritual I embraced throughout the trip. There’s something deeply restorative about easing into the day in hot, open waters, book in hand. After a leisurely breakfast, we caught the 1.5-hour train to Kyoto.
Upon arriving and settling into our hotel, we set out to explore. Our first stop was the Kyoto National Museum, where we marveled at exquisite artifacts showcasing Japan’s history and artistry. From there, we visited the Sanjusangendo Temple, home to the awe-inspiring 1,001 statues of Kannon, the goddess of mercy.
As we wandered, we stumbled upon a serene cemetery, its weathered gravestones surrounded by lush greenery. Our walk led us to Kiyomizu-dera, a grand temple perched on a hillside with panoramic views of the city below.
The afternoon flowed into evening as we explored the atmospheric streets of the Gion district, famed for its traditional wooden machiya houses and sightings of geisha gliding through lantern-lit alleys. We ended the day with a delicious sushi dinner along the Kamo River, where the lights and sounds of bustling night life added to the charm.
Day 8: Immersed in Kyoto’s Cultural Riches
Our second day in Kyoto was a dive into the city’s rich cultural heritage. We began with a visit to a traditional Edo-style tea house, where we learned about the art of Japanese tea ceremonies. Next, we toured a cultural museum, tracing the history of Kyoto through various eras.
A highlight of the day was exploring the Kyoto Imperial Palace, where a free audio tour brought the palace grounds to life with fascinating stories of the imperial family and court life.
For lunch, we enjoyed a vegetarian feast, including savory potato pancakes grilled right at our table. Re-energized, we visited the iconic Kinkaku-ji (the Golden Pavilion). Its shimmering gold exterior reflected beautifully in the surrounding pond, creating a scene straight out of a postcard.
We ended the day with a peaceful walk along the Philosopher’s Path, a stone pathway following a cherry blossom-lined canal. The gentle sounds of flowing water and rustling leaves made it the perfect setting to reflect on the day. Dinner was a bowl of rich, flavorful vegan ramen that warmed us after a long day of exploration.
Day 9: A Rainy Day of Rest and Simple Pleasures
Kyoto graced us with only a single rainy day on our final full day in the city. Armed with umbrellas, we embraced the slower pace, exploring a local mall where we found unique gifts and sampled delightful mochi.
Lunch was a standout at the train station—a memorable tofu muli-course meal at a restaurant located within the train station. Kyoto is renowned for its tofu, and this meal didn’t disappoint, offering a variety of textures and flavors that highlighted the simplicity and elegance of the cuisine. It was a restful day, perfectly timed to recharge after several days of constant exploration.
Kyoto’s charm lies in its harmonious blend of historical reverence and serene beauty. Every moment here, from the bustling streets of Gion to the tranquil Philosopher’s Path, felt imbued with a sense of timelessness. Whether you’re drawn to its spiritual sites, cultural richness, or simply the quiet magic of its tea houses and gardens, Kyoto offers a deeply enriching experience that lingers long after you’ve left.
The Izu Peninsula: Coastal Charm and Birthday Bliss
After the cultural richness of Kyoto, we ventured to the Izu Peninsula, a place that combines stunning natural beauty with a relaxed, seaside vibe. Izu peninsula is a great place to stop on your way back to Tokyo. The journey there requires a local ferry across the bay in front of Mt. Fuji, which is such a treat! From the moment we arrived, the peninsula’s charm captivated us, making it an unforgettable part of our journey.
Day 10: Arrival and Coastal Exploration
Our journey to the Izu Peninsula began with a scenic train and ferry ride, offering glimpses of emerald green islands dotting the horizon. Once there, we were greeted by the laid-back atmosphere of a small coastal town.
Our stay was nothing short of spectacular—a ryokan with sweeping ocean views, two floors of soothing onsens, and a bountiful buffet, all for just $100 a night! It quickly became a highlight of the trip.
After settling in, we spent the afternoon hiking the nearby hills, rewarded with breathtaking views of the coastline and distant islands. Later, we strolled along the beach, the sound of waves gently crashing against the shore. The combination of fresh ocean air, stunning scenery, and peaceful surroundings made for a rejuvenating day.
Day 11: A Birthday to Remember
My birthday was nothing short of magical, celebrated amidst the serene beauty of the Izu Peninsula. The area reminded me so much of Northern California, with its rugged coastline, lush green cliffs, and small, charming towns nestled along the ocean.
We started the day hiking through forested trails that opened up to dramatic coastal views. Being the off-season, the area was wonderfully quiet, allowing us to fully appreciate its natural beauty without the usual summer crowds.
For lunch, we discovered an incredible sashimi restaurant. The fish was so fresh and delicately prepared that it easily became the best sashimi I’ve ever tasted—a true birthday treat.
The day continued with a peaceful walk along a canal that seemed to stretch endlessly, leading us to an unexpected gem: a quaint, free local museum showcasing the area’s history and culture. It was a delightful find that added a touch of whimsy to the day.
After one final hike through scenic trails, we caught a bus back to our ryokan. The evening was perfect: a decadent buffet, complete with strawberry cream cake, followed by a long soak in the ocean-view onsen. As the warm waters enveloped me and the rhythmic sound of the waves filled the air, I felt an overwhelming sense of gratitude for this unforgettable birthday experience.
The Izu Peninsula’s combination of coastal beauty, charming towns, and tranquil onsens makes it a must-visit destination for those seeking a more relaxed, nature-focused experience in Japan. Whether you’re hiking its scenic trails, savoring fresh seafood, or simply soaking in an oceanfront onsen, the Izu Peninsula offers a perfect blend of adventure and relaxation. It was the ideal setting for a birthday celebration and a highlight of our journey.
Back to Tokyo: A Memorable Finale
After our time on the serene Izu Peninsula, we made our way back to Tokyo to close out our journey. Despite the rain, the city’s energy and charm made our final days equally captivating and fulfilling.
Day 12: A Rainy Return
Our journey back to Tokyo was a quiet one, with rain accompanying us for most of the day. Thankfully, we spent much of the time on trains, watching the cityscapes and countryside blur past.
This time, we stayed in Koenji, a vibrant neighborhood known for its live music and nightlife, an exciting contrast to the tranquility of the Izu Peninsula. Our cozy apartment provided a convenient base, and though the rain persisted, it only added to the city’s moody, atmospheric allure.
Day 13: Exploring Tokyo’s Cultural Gems
Our last full day in Tokyo was filled with unforgettable experiences. We began at the Imperial Palace, a historic site surrounded by expansive gardens that felt like an oasis in the bustling city.
From there, we visited a historic museum and a typography museum, each offering fascinating insights into Japan’s past and its artistic legacy. For lunch, we picked up beautifully arranged bento boxes and enjoyed them in the serene Imperial Gardens. The combination of exquisite food and the tranquil setting was a highlight, and we still find ourselves dreaming about that meal.
The afternoon brought us to the Tokyo TeamLab immersive exhibit. Words can hardly do justice to the mind-blowing experience of stepping into this world of interactive digital art. Each installation was a dazzling fusion of light, sound, and motion, creating an otherworldly sensory adventure.
We wrapped up the day with one final bowl of Tokyo’s finest vegan ramen, savoring every bite and reflecting on the incredible journey we’d had.
Day 14: Farewell to Japan
The morning of our departure was bittersweet. As we made our way to the airport, we couldn’t help but feel a deep sense of gratitude for the experiences, sights, and flavors we had enjoyed over the past two weeks. Japan had been everything we hoped for and more—a perfect blend of tradition, modernity, and natural beauty.
Returning to Tokyo felt like coming full circle. The city’s vibrancy, cultural richness, and culinary delights made for a perfect conclusion to our adventure. From the peaceful cherry blossom-lined streets to the dazzling digital art of TeamLab, Tokyo offered a lifetime’s worth of memories in just a few days.
Japan left an indelible mark on us, and as we boarded the plane back to Los Angeles, we knew it wouldn’t be long before we’d start dreaming of our return.
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Travel with Raleigh 
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