Morning: Land at Haneda Airport and take the Keikyu Line to Shibuya Station (≈30 min). Check into your hotel and freshen up.
Afternoon: Stroll around Shibuya Crossing, explore the Hachikō Statue, and enjoy a quick snack at Katsudon‑ya Zuicho for a kid‑friendly katsudon.
Evening: Walk to Mo‑Mo‑Paradise Shibuya Center Street for an all‑you‑can‑eat shabu‑shabu dinner, then unwind at the hotel.
Find HotelsMorning: Visit the trendy boutiques of Harajuku, then head to Age.3 GINZA for their famous egg sandwich breakfast.
Afternoon: Explore Meiji Shrine, then enjoy a hearty bowl of udon at Kirimugiya Jinroku near Shinjuku‑gyoemmae Station.
Evening: Dine at Kaiten Sushi Ginza Onodera for sushi on a conveyor belt, and later enjoy the neon lights of Shibuya at night.
Find HotelsMorning: Take the JR Yamanote Line to Tokyo Station, then the JR Keiyo Line to Maihama (≈45 min). Enter Tokyo Disneyland and head straight to the Fantasyland castle.
Afternoon: Watch the parade, ride family‑friendly attractions like “It’s a Small World,” and have lunch at the park’s “Grandma’s Kitchen” for kid‑approved meals.
Evening: Stay for the fireworks, then return to Shibuya by train. Grab a late snack of ramen at Iruca Tokyo Roppongi if you’re still hungry.
Find HotelsMorning: Breakfast at Unagi Semmonten Aikawa in Takadanobaba for grilled eel, a local favorite.
Afternoon: Explore Asakusa’s Senso‑ji Temple, then head to Sushi Dai in Toyosu for the ultimate sushi experience (arrive early!).
Evening: Visit the bustling streets of Ginza, enjoying tempura ramen at Ginza Hageten** before returning to Shibuya.
Find HotelsMorning: Check out and board the JR Tokaido Shinkansen from Tokyo to Shin‑Fuji (≈1 h). Store luggage in lockers and take a local bus to the Fujiyama 5th Station.
Afternoon: Enjoy panoramic views of Mt. Fuji, walk the short trails, and have a picnic with local snacks.
Evening: Return to Shin‑Fuji Station, take a train back to Tokyo, and stay one more night in Shibuya for a relaxed evening.
Find HotelsMorning: Check out and ride the JR Tokaido Shinkansen from Tokyo to Shin‑Osaka (≈2.5 h). Transfer to the Osaka Metro and check into your hotel in Dotonbori.
Afternoon: Explore Dotonbori’s iconic Glico sign, stroll along the canal, and try street foods like takoyaki.
Evening: Dine at Yasubei of Ebisu (though in Tokyo, you can swap for a local izakaya in Osaka) for gyoza and share plates, then enjoy the neon nightlife.
Find HotelsMorning: Visit Osaka Castle and its park, letting your son run around the wide lawns.
Afternoon: Head to the Osaka Aquarium Kaiyukan for an unforgettable marine experience.
Evening: Return to Dotonbori for dinner at Shodai (curry udon) and wander the lively streets.
Find HotelsMorning: Take the Kintetsu Nara Line from Osaka to Nara (≈45 min). Feed the friendly deer in Nara Park.
Afternoon: Visit Todai‑ji Temple to see the Great Buddha, then enjoy a bento lunch at a local eatery.
Evening: Return to Osaka, relax at your hotel, and have a light dinner at Menya Ittō (tsukemen) via a short subway ride.
Find HotelsMorning: Explore Shinsaibashi Shopping Arcade for souvenirs and snacks.
Afternoon: Visit the Osaka Museum of Housing and Living for interactive exhibits that kids love.
Evening: Enjoy a final Osaka dinner at Kaiten Sushi Ginza Onodera (Osaka branch) for conveyor‑belt sushi.
Find HotelsMorning: Leisurely breakfast at a local café, then revisit any favorite spots in Dotonbori.
Afternoon: Pack luggage, purchase last‑minute souvenirs, and enjoy a relaxed stroll in the Umeda Sky Building’s observatory.
Evening: Early dinner at Fuunji Tokyo Ramen Yokocho (if staying in Tokyo) – otherwise choose a nearby Osaka ramen shop, then rest for departure.
Find HotelsMorning: Check out, take the Nankai Airport Express from Namba to Kansai International Airport (≈45 min) to catch your 10 am flight back to Singapore.
Afternoon: Flight departure.
Evening: Arrive home.
Find HotelsFor a more relaxed pace, consider dropping the Nara day trip and spending an extra half‑day in Osaka’s Universal Studios, which is great for kids. If you need to shorten the itinerary, skip the Fuji visit and allocate that time to explore more of Tokyo’s museums or parks; the Shinkansen tickets are refundable up to a certain amount. Pack a portable Wi‑Fi router for seamless navigation, and purchase a 7‑day Japan Rail Pass (adult) and a child pass to save on the long‑distance trains.