Morning: Land at Haneda Airport and take the Keikyu Line to Shibuya Station (≈30 min). Check‑in at your Shibuya hotel and freshen up.
Afternoon: Stroll through the bustling Shibuya Crossing and explore nearby shopping streets. Treat the family to a casual lunch at Katsudon‑ya Zuicho for its famous pork cutlet bowl.
Evening: Wander the illuminated streets of Shibuya Center‑Street and enjoy an all‑you‑can‑eat shabu‑shabu dinner at Mo‑Mo‑Paradise Shibuya. Early bedtime prepares you for tomorrow’s busy schedule.
Find HotelsMorning: Visit the trendy Harajuku area, walk Takeshita Street, and snap photos at the Meiji Shrine’s forested grounds.
Afternoon: Head to Ginza for a light lunch at Age.3 GINZA (egg sandwich). Afterwards, explore the upscale shopping district and stop by Kaiten Sushi Ginza Onodera for a sushi tasting.
Evening: Return to Shibuya and dine at Yasubei of Ebisu, an izakaya known for its gyoza. Finish the night with a walk to Shibuya Sky for a panoramic city view.
Find HotelsMorning: Take the JR Yamanote Line to Tokyo Station and transfer to the Musashino Line for a direct bus to Tokyo Disney Resort. Arrive early to secure FastPasses for the main attractions.
Afternoon: Explore Tokyo Disneyland with a focus on kid‑friendly rides like Pooh’s Hunny Hunt and Monsters, Inc. Ride. Grab a quick bite at the park’s Unagi Semmonten Aikawa stall for grilled eel.
Evening: Watch the spectacular fireworks show before heading back to Shibuya via train. Enjoy a relaxed dinner at Iruca Tokyo Roppongi (ramen) after a short subway ride.
Find HotelsMorning: Start at Menya Ittō in Shin‑Koiwa for a hearty tsukemen broth. Then hop on the JR Sobu Line to Tokyo’s Fuunji Tokyo Ramen Yokocho in Yaesu.
Afternoon: Continue the noodle quest at Higashi‑Ikebukuro Taishoken – Main Shop. Take a short break at a nearby park before heading to Kirimugiya Jinroku for udon and tempura in Shinjuku.
Evening: End the day with fresh sushi at Sushi Dai in Toyosu. Return to Shibuya for a quiet night or explore a local karaoke spot.
Find HotelsMorning: Board the shinkansen from Tokyo Station to Odawara (≈35 min) and transfer to a local train to the Fuji Five Lakes region. Visit Lake Kawaguchi for iconic Mt. Fuji views.
Afternoon: Take a scenic bus around the lakes, then return to Odawara for the shinkansen to Shin‑Osaka Station (≈2 h 15 min). Check‑in at your Dotonbori hotel.
Evening: Explore the neon‑lit Dotonbori promenade, try takoyaki from a street vendor, and dine at a local okonomiyaki restaurant.
Find HotelsMorning: Take the Osaka Loop Line to Osaka Castle. Wander the castle grounds and learn about its history at the museum.
Afternoon: Head to Namba for shopping at Shinsaibashi‑Suji and a snack at a nearby crepe stand. Visit the Kuromon Ichiba Market for fresh seafood.
Evening: Return to Dotonbori for dinner at a family‑friendly izakaya serving kushikatsu. End the night with a river cruise to see the illuminated Glico sign.
Find HotelsMorning: Take the JR Kyoto Line to Kiyomizu‑dera Temple. Walk the historic Higashiyama streets and enjoy a sweet treat at a local café.
Afternoon: Visit Fushimi Inari Taisha and hike through the iconic torii gates. Return to Osaka via train.
Evening: Relax back in Dotonbori, perhaps trying a new ramen shop or revisiting your favorite takoyaki stall.
Find HotelsMorning: Catch the JR Yumesaki Line to Universal Studios Japan. Start with the Wizarding World of Harry Potter for a magical experience.
Afternoon: Enjoy family‑friendly rides such as Minion Park and Jurassic Park. Grab lunch at the park’s Mel’s Drive‑In for classic burgers.
Evening: After the park closes, return to Dotonbori for a late dinner of Osaka‑style grilled seafood.
Find HotelsMorning: Visit the Umeda Sky Building observatory for city views. Wander the nearby Grand Front Osaka mall.
Afternoon: Spend time at Tennoji Park and the zoo, a fun stop for your son. Have a light lunch at a nearby café.
Evening: Explore the retro streets of Shinsekai and try the famous kushikatsu at a local eatery. Return to the hotel for a restful night.
Find HotelsMorning: Choose a relaxed activity such as a river bike ride along the Okawa River or a visit to the Osaka Aquarium Kaiyukan.
Afternoon: Do any last‑minute souvenir shopping in Namba or revisit a favorite spot. Enjoy a casual snack of taiyaki.
Evening: Celebrate the trip with a farewell dinner at a high‑end sushi restaurant in Harukas (Osaka’s tallest building) for stunning night views.
Find HotelsMorning: Check out of the hotel and take the Nankai Airport Express from Namba to Kansai International Airport (≈45 min). Arrive by 7:30 am for your 10:00 am flight back to Singapore.
Find HotelsTo shorten the trip, you could skip the Kyoto day‑trip and the Universal Studios visit, using the saved time for a more relaxed pace in Osaka. Conversely, if you’d like to extend your stay, add an extra night in Kyoto or a day trip to Nara from Osaka for more cultural experiences. The food list you provided is mainly in Tokyo, so plan to fit those meals into the first four days; Osaka offers its own specialties—don’t miss takoyaki, okonomiyaki, and kushikatsu while you’re there.