Perfect 5-Day Tokyo Itinerary 2025

When we Singaporeans first arrive in Tokyo, there is always a hushed "wow" reaction. Perhaps it's the huge scope of the skyline grinder, but it feels milder than ours. Perhaps it is the mix of centuries-old shrines with modern cafés and neon-lit towers. The pace is quick, but there's a softness in the air, especially in spring when flowers float like snow. Tokyo's weather can surprise you with its dry winters, lush summers, and clear, beautiful light all year round.

This guide divides the city into easy half-day experiences in the morning, afternoon, and evening. Allowing you to mix and match activities based on your mood, energy level, or even weather. Each offers important details, wonderful food stops, and the ideal times to visit. I'll also recommend the best spots to stay in Tokyo based on your preferences. There's something for everyone, whether you enjoy cuisine hopping, skyline chasing, or taking in culture at your own speed.

🏙️ Day 1: Morning in Shibuya – Classic Tokyo & City Views

🛣️ Getting There & First Impressions

I started my Tokyo experience in Shibuya, because where else can you get that instant "I'm really in Tokyo" feeling? As soon as I stepped out of Shibuya Station's Hachiko Exit, the energy hit me like a wave. Crowds crossing in all directions, big screens displaying pop culture icons, and the renowned Shibuya Scramble humming with activity. I was amazed and slightly overwhelmed, but it's the kind of craziness you quickly come to enjoy.

🛍️ Wandering & Discovery

After taking a photo with Hachiko and crossing myself (again!), I went up to Shibuya Sky at the top of Shibuya Scramble Square. Pro tip: purchase your ticket online the day before it sells out quickly, especially on weekends! The elevator ride up feels like a science fiction film, and when the doors open? Pure magic. Panoramic views of the entire city, with Mount Fuji visible in the distance on clear mornings. I stayed longer than expected simply drinking it all up, lying back on the sky hammocks with the breeze in my face. Tokyo felt limitless.

☕ Snack / Rest / Café Highlight

Coming down from the clouds (literally), I stopped by Streamer Coffee Company tucked just behind the main crossing. Their military latte, matcha with espresso sounded like a weird mix but totally worked. It’s a good place to catch your breath and watch Tokyoites go about their morning rush.

🌀 What I’d Do Differently

I got to Shibuya Sky a little too late and the sun was already getting strong. So for softer light and fewer reflections on the glass, I’d aim for around 9:30 AM. It’s also cooler up there before midday heat kicks in.

📸 Best Moment or Surprise Find

Hands down, my favorite moment was standing at the edge of the Shibuya Sky helipad, wind in my hair, music playing softly through speakers, and Tokyo stretching out forever. It made the whole trip feel real.

🎮 Day 2: Afternoon in Harajuku – Pop Culture & Quirky Tokyo

🛣️ Getting There & First Impressions

I stepped off the JR Yamanote Line at Harajuku Station, expecting a few cute shops but Takeshita Street? Total sensory overload (in the best way). It was packed with teens in anime-inspired outfits, cotton candy taller than my head, and shops blaring K-pop at full volume. For a moment, I almost turned around. It was that chaotic. But I pushed through, and honestly? I’m so glad I did.

🛍️ Wandering & Discovery

Beyond the main drag, the real fun began. I wandered into hidden side streets like Cat Street and Ura-Harajuku, where independent boutiques, vintage stores, and quirky photo booths live. WEGO had some surprisingly cool pieces, and I got a cheap-but-fun souvenir hoodie. Just when I thought I’d seen it all, I stumbled into Design Festa Gallery a colorful maze of mini-art studios and local creations. It was a quiet pocket in all the madness.

☕ Snack / Rest / Café Highlight

I took a break at Eddy’s Ice Cream, where the soft serve comes with crazy edible decorations. I ordered one with rainbow stars and a unicorn cookie because why not? It was overpriced, sure, but sitting by the window watching the Harajuku crowd parade was pure entertainment.

🌀 What I’d Do Differently

Next time, I’d come a bit later around 2 PM when the morning rush dies down a little. And I’d definitely wear comfier shoes. Those side streets look short on the map but are deceptively endless.

📸 Best Moment or Surprise Find

The moment I found a tiny mural-covered alley behind a vintage shop and watched a local artist painting live it felt like discovering Tokyo’s heartbeat, hidden behind the glitter.

🚉 Day 3: Morning in Nikko – Temples, Trails & Tranquility

🛣️ Getting There & First Impressions

Catching the early Tobu Limited Express train from Asakusa, I dozed off for a bit and woke up to a completely different world: misty hills, tall cedar trees, and fresh mountain air. Nikko felt like someone had hit pause on Tokyo’s buzz. The small-town station had a sleepy charm, and the bus ride up to the heritage area gave me my first glimpse of how spiritual and nature-rich this place really is.

🛍️ Wandering & Discovery

I started at Toshogu Shrine, and even though I’d seen photos, nothing prepared me for the intricate carvings and gold-leaf detail. It was a bit crowded at first, especially near the Yomeimon Gate, but as I wandered deeper into the forested complex, everything became still and quiet. Climbing the steps to Tokugawa Ieyasu’s tomb felt like stepping back in time, with only the sounds of rustling leaves and my own breath.

☕ Snack / Rest / Café Highlight

After exploring, I grabbed a seat at Hippari Dako, a local joint near the station. Their yakitori and yuba (tofu skin) dishes were perfect after a chilly walk. It’s tiny and a bit rustic, but that’s part of the charm plus, I loved the handwritten notes from travelers all over the world taped to the walls.

🌀 What I’d Do Differently

I underestimated how chilly and damp Nikko could get, even in spring. A light waterproof jacket would’ve saved me from the drizzle that came out of nowhere. Also: wear comfy shoes, those shrine steps are no joke!

📸 Best Moment or Surprise Find

There was this quiet trail behind Rinnoji Temple, barely marked, that led me to a tiny moss-covered bridge over a creek. No one else was around. That moment of solitude? Absolutely unforgettable.

🏯 Day 4: Afternoon in Ueno – Museums, Tranquility & Timeless Charm

🛣️ Getting There & First Impressions

I hopped off the train at Ueno Station just after lunch, expecting a typical busy Tokyo neighborhood but the moment I stepped into Ueno Park, it felt like I’d entered a totally different rhythm. The park opened up with broad walkways shaded by old trees and framed by lotus ponds. Even on a weekday, there were families, students sketching, and elderly couples out for a stroll. It had a nostalgic kind of calm, like a pause in the middle of the city’s heartbeat.

🛍️ Wandering & Discovery

I started with the Tokyo National Museum, and wow it was so much more than I expected. The building itself felt like stepping into an Edo-era storybook, and the samurai armor displays were next-level. I nearly skipped the Hyokeikan building because I was short on time, but its mix of Western architecture and Japanese heritage turned out to be one of the coolest surprises. If you’re into photography, the symmetry and soft afternoon light there are gold.

☕ Snack / Rest / Café Highlight

By 3pm, I was ready for a break, so I wandered toward Ueno no Mori Park Side Café. It’s right by the museums and has terrace seating that overlooks the greenery. I ordered a matcha latte and their seasonal chiffon cake light, fluffy, just sweet enough. Sitting outside with a view of the park made the whole afternoon feel longer in the best way.

🌀 What I’d Do Differently

I didn’t realize how massive the park is, so I ended up walking in circles trying to find the Tokyo Metropolitan Art Museum. Downloading the park map ahead of time would’ve saved my legs (and a bit of time).

📸 Best Moment or Surprise Find

Just as I was leaving, I caught sight of a lone street musician near Shinobazu Pond, playing the shamisen under a golden sky. A small crowd had gathered, totally still, just listening. It was this beautiful, unscripted ending I hadn’t expected so Tokyo, yet so timeless.

🛍️ Day 5: Morning in Shimokitazawa – Cozy Cafés & Indie Finds

🛣️ Getting There & First Impressions

I caught the Odakyu Line to Shimokitazawa Station just after breakfast, thinking I’d do a quick walkaround before heading elsewhere but I ended up staying all morning. As soon as I stepped out of the station, it felt like Tokyo had taken a deep breath. The streets were narrow and calm, lined with vintage stores, tiny bookstores, and cafés that looked like someone’s living room. There was a lived-in charm here, the kind that invites you to linger.

🛍️ Wandering & Discovery

I wandered into New York Joe Exchange, which used to be a public bathhouse and is now a beloved secondhand clothing spot. It was fun, chaotic, and full of personality just like the neighborhood. Then I stumbled into Village Vanguard Diner (not to be confused with the bookstore) where they played groovy ‘90s J-pop and served me one of the most unexpectedly good teriyaki burgers I’ve ever had. It wasn’t part of the plan, but that’s the point Shimokita rewards spontaneity.

☕ Snack / Rest / Café Highlight

Needing a caffeine boost, I ducked into Frankie Melbourne Espresso. It’s tiny, Aussie-run, and absolutely nailed my flat white. I took my coffee upstairs, where there's a little lofted seating area. It's the perfect spot to watch the quiet buzz of morning life outside. A local next to me was journaling, and I ended up chatting with them about Tokyo’s café scene. It felt so un-touristy, like I’d cracked some secret corner of the city.

🌀 What I’d Do Differently

I made the rookie mistake of arriving right at 10 a.m., but many shops don’t open until 11. Next time, I’d take it even slowerarrive around 11, grab a late brunch, and let the vibe lead the way. Shimokitazawa isn’t made for schedules.

📸 Best Moment or Surprise Find

Just before leaving, I found Flamingo, a vintage shop with retro American fashion that’s curated like a museum. The fitting room was an old red phone booth, and somehow trying on a jacket there turned into a 20-minute conversation with the staff about their favorite cafés in the area. It was one of those rare travel moments that felt effortlessly local and personal 👕✨.

🎋Lets Go To Tokyo!

Tokyo has this way of staying with you like a song that keeps playing in your head long after it’s over. One moment you’re lost in the rush of Shibuya’s scramble, the next you’re sipping matcha in a garden so still it feels like time paused just for you. That contrast, that rhythm it’s what makes Tokyo unforgettable. Sure, the metro can be a maze at first (and yes, you will get on the wrong train once), but it’s all part of the adventure. If you’re already eyeing flights to Tokyo, I’d say go for it. You’ll find some of the best hotels in Tokyo hidden among the very streets I wandered, and there are some great travel promotions for Tokyo popping up lately too. Wherever your Tokyo journey takes you, I hope it leaves you with stories worth retelling.