5 Day Tokyo Itinerary: Culture, Shopping and Sakura

After our unforgettable trip to Chiang Mai, this was my second “mommy break” getaway, as well as my second visit to Japan.

It began on a random weekday, when I realised I wanted to hit the pause button on life, and use that 5-year Japan visa which has been idling in my passport. Within less than a month, I booked the flight, left my baby with her wonderful dad and took off to reunite with an old travel companion, in order to rediscover Japan together.

Japan has a complicated history and politics, and I’m still not sure how I feel about a lot of it, but I will say this: the place still fascinates me with its air of mystery, magic, and laser-sharp precision. In that sense, Tokyo is the essence of Japan in microcosm. It is full of life and stories you could spend the rest of your days chasing, from the glittering night sky reflected on Tokyo Tower to the silken brushstrokes of cherry blossoms in early spring to the cacophonous neon madness of Shibuya during rush hour.

Day 1: Roppongi Hills & First Impressions

I hadn’t been on a red-eye flight in ages, and let’s be real—both of us were a little terrified. Our bodies don’t take kindly to red-eyes the way they used to, but daytime flights were almost double the price. From Singapore, the red-eye flight takes about 6.5 hours (leave around midnight, arrive 6.5am). The good news is the immigration process was super-fast if you fill in that Visit Japan Web form in advance.

We landed in Narita, and after some aimless wandering in the airport, stumbled upon a breakfast place that actually served us by the time we got to Terminal 1 (why do foreign airports always have to spread their restaurants all over the place?). The restaurant was called Ochazuke, and it specialised in tea-rice bowls. They aren’t very common in Singapore, so it was a bit of a novelty—and it turned out to be delicious, and not so bad on the wallet either! We liked it so much we had breakfast there on our return trip too.

We stayed in Ginza this time, and if you’ve ever walked Orchard Road with arms full of luggage while thinking, “Wait, Orchard Road has a bajillion luxury brands but it’s not even as posh as this?”, welcome to Ginza. We checked in, changed our clothes and went for a stroll to Omotesando.

Omotesando didn’t hit me as much as Chongqing at first, but if it was the quirky side-streets with their carefully curated high-end boutiques and cafes and record/vintage shops that gave Seoul its vibes, then Omotesando was very much a Gen Z heaven.

🍴 Lunch: A Japanese-style hamburg steak joint called Ka. Set meals here were delicious and reasonably priced (about ¥3000).

At some point that evening, we went up to the Roppongi Hills Observation Deck, pre-booked online (PS: don’t buy from third-party sites unless you really want a very specific time slot). We arrived about 30 mins early, as sunset was at about 6.30pm, and decided to catch the views both in the day and night.

The views were mind-blowing. Unfortunately, my camera skills failed me.

Day 2: Kamakura Day Trip — Tranquility by the Sea

I am not a die-hard Slam Dunk fan, but I did grow up watching the anime. That said, Kamakura didn’t make my list because of the anime. I admit it: the image of the coastline traced by a train snaking through the headland, a breeze in our hair, the stillness of a sleepy sea-side town—this was the vision I came to Kamakura for.

We visited on a Friday. “Will it be crowded?” we wondered naively. Uhm, yes.

Head and shoulders (literally) crammed cheek by jowl with a jumble of Japanese salarymen and women tourists on the Enoshima Electric Railway (Enoden). The stretch of coastline from Enoshima to Kamakura is a must-visit in Tokyo, so I won’t regale you with a blow-by-blow of the line.

But a few of my favourite stops on the line:

Kamakura Station: Stroll down Komachi Street for some street food and shop for souvenirs.

Hase Station: Check out Hasedera Temple (¥400 entrance, hydrangeas if you go at the right season), and you have to see the world-famous Kamakura Daibutsu.

Shichirigahama: Scenic seaside restaurants. Hawks will circle overhead, and watch out for the wind here—it comes straight from the sea and will whip your hair back.

Kamakura Kōkōmae Station: Ah, the Slam Dunk-spot. Trust me when I say that it will be packed. But the side road running towards the sea gives a more peaceful vista.

🍴 Lunch: We visited a famous seaside café called Double Doors and had their signature beef garlic fried rice. Worth the 30 min wait!

🌃 Night: Back in Tokyo that night, we went to Omoide Yokocho (Memory Lane) in Shinjuku, a tiny alleyway of local izakayas. There’s not much touristy stuff here but you go for the neon-lit ambience, the sizzle of skewers and the waft of oil hitting your face as the staff at these cozy restaurants shove you out of the way to get at their new customers. Trust me, you feel like you’re in a movie—turn your phone camera on and let those candid shots roll.

PS: Heads up, some places do not have English menus and photography is not always allowed.

One thing led to another and we ended up at the first izakaya we walked into, ordered a whole plate of 10 yakitori skewers and some side dishes. Total bill for two: less than ¥4000. Absolute sanity in a bottle.

Day 3: Tokyo DisneySea — Kids Stuff for Her, Maybe a Little for Me

Hong Kong Disneyland (twice), no Shanghai Disneyland, and somehow I’m here—not for myself, but to choose soft toys for my daughter. I didn’t expect to find that childlike wonder again… but DisneySea still holds a certain magic.

Tips for Adults Visiting DisneySea

• ✅ Book on Taobao for about ¥300 (cheaper than the official site).
• ✅ Try to avoid weekends and holidays.
• ✅ Get there early. We arrived at the gates at 9am and still had to queue for 30 mins.
• ✅ Link your ticket to the Disney Resort App as soon as you arrive and get your DPA (paid, skip-the-line passes) for all the popular rides you want.

🎢 Toy Story Mania (eh) and Tower of Terror (pretty fun!) were our picks, along with a weird water ride where they just spun us around for 15 mins—don’t do this if you are susceptible to midday sun and spinning in a straight line.

🍝 In my defence, we did not expect lunch to be a pleasant experience. It was overpriced and underwhelming (which we knew going in). Not even the ice cream stalls were spared long lines.

📸 Photography is fine, although the EPCOT Countries are especially photogenic.

✨ The highlight of the day for me, by far? Dinner at Teppanyaki Ginza Ji.
No frills. Just 7–8 seats and we were the first customers in. We had the set that included foie gras and premium wagyu beef. No alcohol, and the bill came to ¥30,000 a person. It was by far the best teppanyaki meal I’ve had, and to be honest Singapore doesn’t even come close.

Day 4: Asakusa + Shopping in Tokyo

I was in Asakusa and suddenly realised that this was basically the Japanese version of a Chinese old town—charming old architecture, streets and streets of shopping alleyways, and a neverending procession of snacks stalls. I even found pineapple buns stuffed with ice cream here.

The café we stopped at that day had a very retro interior, but they also offered 2 different seating styles: the regular downstairs counter versus the more traditional tatami-floor upstairs seating area.

⛩️ In the distance, we could see Tokyo Skytree soaring over the city skyline.

We lined up for this famous tonkatsu place. Think of it like Japanese katsu sandwiched inside Chinese char siu bao buns. Pork cutlets juicy on the inside with onions, doused with a sweet sauce.

Tokyo Shopping Picks

✈️ Luxury Goods: Ginza was next-level. At today’s exchange rate with the tax refund (about 10% refund), Tokyo is cheaper than both Singapore and China. Celine and LV had good prices.

🛍️ Second-Hand Boutiques: Still better than Singapore. Omotesando and Shinjuku were the best.

👗 Japanese Street Fashion: Snidel, Moussy, Murua, and other Japanese fashion brands hard to find in SG these days. We shopped at Lumine EST in Shinjuku. Price range: ¥4000 – ¥10,000.

🧴 Beauty/Skincare: The best prices and variety are in Japan. Donki beats prices in Singapore.

👟 Streetwear: Shinjuku PARCO. I picked up an Undercover x UC tee for my husband.

🍰 Gifts: Skip Tokyo Banana. Line up inside Tokyo Station for NY Perfect Cheese (only available at the counters inside Tokyo Station).

Day 5: Farewell Tokyo – Rain & Tsukiji Market

It rained our last day. A small miracle during the rainy season, although this time we finally got to experience the famous umbrella-storm in the Shibuya crossing.

Woke up early and went to Tsukiji market. I am not much of a seafood person but, well, when in Tokyo.

I shared a beef and uni bowl with my friend. It was good, but rich. At ¥3500 per bowl, not cheap either but still worth it.

We returned to the same ochazuke shop at Narita Terminal 1 to cap off the trip.

Transportation Tips

✈️ Flights

We flew with Zipair (budget airline) on a last-minute deal. Round trip cost us SGD $720 (~¥3600). Big plane with free Wi-Fi = better than expected.

🚇 Tokyo Subway

Terrible system, even for a seasoned traveler. Pro-tip (for lazy people like me):

• Buy a multi-day metro pass if you’re staying in the city center. Valid for most lines with the circle icon in your ticket wallet.
• JR, Odakyu and Keikyu lines will require separate tickets.
• If you misplace your pass like I did, you will need to buy another one.
• Buy a Suica card or load onto your Apple Wallet. Just don’t accidentally load too much onto your card, you can’t refund the digital one.
• Taxis are crazy expensive. Don’t even bother.
• Google Maps is your friend for route planning.

🚌 Airport Bus (Narita to Tokyo)

Buy your low-cost bus ticket (¥1300) at the Narita T1 kiosk and you’re in for a 70-min ride to Tokyo with Wi-Fi and charging ports en route.

You can also take the return bus from Tokyo Station (Yaesu Exit) and scan your Suica or purchase directly from the machine.

How to Get to Kamakura

Two options:

• From Shinjuku, take the Odakyu Line to Fujisawa and board the Enoden from there. Budget travelers can get the Enoshima-Kamakura Freepass.
• From Shimbashi or Tokyo Station, take the JR to Kamakura and get the Enoden one-day pass at the Kamakura JR Station.

💡 JR has reserved “Green Cars”—you have to top up about ¥1000 to board one without a seat.

Accommodation

🏨 Sotetsu Fresa Inn Ginza-Sanchome

We stayed in Sotetsu Fresa Inn Ginza for 4 nights.

• 4 nights = SGD $970 (~¥4850) without breakfast
• Tiny room, basic toiletries (self-service), average Wi-Fi
• Good location near Ginza

Additional Travel Tips

• Suica card does not work with all credit cards (mine from OCBC does not). Best to check before loading.
• Garbage bins are hard to find. Bring a bag for your own trash.
• Late May is a weird time for flower viewing in Japan—the roses are starting to wither, hydrangeas not yet in bloom.
• Lots of places will require reservations. We missed a few good ones by not booking ahead.
• Walk and travel light. There are few elevators in the Tokyo subway system and stairs upon stairs.

Final Thoughts

This Tokyo trip is a blast for me!

My feet are sore, my heart is full, and I am nearly back to zero energy, but the memories will sustain me until the next trip…