Dates are flexible. This day-by-day plan is provisional until you choose exact travel dates.
Fly from Louisville to Tokyo, allowing roughly 20–30 hours door to door, including airport time, connections, immigration, and the ride into town. The actual route and arrival airport depend on your flight booking, so don’t assume a particular connection. Leave about three hours for international check-in in Louisville; after landing, budget roughly 30–50 minutes from Haneda or 60–90 minutes or more from Narita to central Tokyo, depending on traffic and your route. Check in near your hotel, hydrate, and rest—the day’s plans should depend on when you actually arrive.
If you have energy, take an easy outdoor walk around Tokyo Station Marunouchi; it’s a good first look at the city without a timed ticket or commitment. Then browse KITTE Marunouchi, next to the station, for Japanese goods and stationery. Shops are generally open around 11 a.m.–9 p.m. (often closing earlier on Sundays and holidays), but check the current hours and your arrival time before counting on a visit. Finish at Soba Kanda for a casual meal, roughly ¥1,000–2,000 per person; confirm it’s open when you go. With ulcerative colitis, ask about broth, toppings, spice, and any ingredients you avoid, and choose a mild, familiar option rather than assuming a dish will suit your triggers. Keep the evening flexible so you can head back to the hotel whenever you need.
Start at Shibuya PARCO when it opens, usually around 11 a.m. (check the current hours before you go). Head to Pokémon Center Shibuya first; it’s popular, so allow extra time for browsing, checkout lines, and any crowd-control or timed-entry system in effect that day. Then continue to Nintendo TOKYO in the same building—an easy next stop, though its character goods and queues can also tempt you to linger. Set a loose shopping budget before you enter; little souvenirs add up quickly.
Take the short walk to PUNYUS Shibuya 109 and browse its playful clothing. The brand is known for offering a broader size range than many Japanese labels, but don’t assume a particular item will fit a US 20: compare garment measurements with the current size chart and ask staff about stock. Shibuya 109 generally opens around 10 a.m. and closes around 9 p.m., but confirm its hours before setting out. After shopping, stroll over to Shibuya Scramble Crossing; watch the waves of pedestrians from the pavement, or take a break at a nearby café before crossing at your own pace.
Finish with ramen at AFURI Shibuya, budgeting roughly ¥1,500–2,500 per person and checking the current branch hours before you go. Menus and customization vary, so ask about broth ingredients, spice, citrus, and toppings; with ulcerative colitis, choose according to your own triggers rather than assuming a dish will be gentle. If you need to explain, show staff a translated note listing ingredients you avoid. The stops are all in Shibuya, so walking is the simplest way to get between them; allow more time than the map suggests for shopping crowds and queues.
Start around 10 a.m. on Takeshita Street, a short walk from Harajuku Station’s Takeshita Exit. It’s liveliest—and often shoulder-to-shoulder—around midday, so an early browse makes it easier to dip into accessory and character-goods shops without feeling swept along. Shop hours vary, but many open around 10 or 11 a.m.; there’s no admission fee. If the crowd gets tiring, step onto a side street for a breather before continuing to Kiddy Land Harajuku. Give its multi-floor character shops about an hour, and check current hours before setting out; it typically opens around 11 a.m.
Walk toward Omotesando for a calmer change of pace and a look through its design and lifestyle shops. Allow roughly 30–45 minutes to browse, then stop at A Happy Pancake Omotesando for a seated sweet break; budget about ¥1,500–2,500 per person, plus drinks. Queues can build, so check whether reservations are available for your day. With ulcerative colitis, ask staff about ingredients and portion options, and choose what feels comfortable for you—menu details and substitutions can vary.
Finish at Meiji Jingu, a pleasant walk from Omotesando. The broad, shaded approach and shrine grounds feel far removed from the shopping streets; allow 1–1.5 hours, including the walk in. Entry to the grounds is free, but the gates close around sunset and the time shifts seasonally, so check the posted hours and head over with daylight to spare. Keep the visit relaxed: the gravel paths can be tiring, and there’s no need to rush through the forested approach.
Allow 3.5–4 hours door to door for the transfer from Tokyo, including getting to the station, the train, and reaching central Osaka. A morning departure leaves the best chance of fitting in the afternoon; check current schedules and reserve seats together if that matters to you. After arriving, head to your Namba or Shinsaibashi hotel to drop your bags and check in—if the room isn’t ready, ask whether they can hold your luggage.
From your hotel, browse Shinsaibashi-suji Shopping Street, a covered arcade with plenty of shops for accessories, souvenirs, and clothes. Many shops open around 10 or 11 a.m. and close in the evening, but hours vary; treat this as a browse rather than a mission, since clothing sizes can be limited and inconsistent. Then walk roughly 10–15 minutes toward Dotonbori for the canal, bright signs, and people-watching. It’s lively, so take your time and don’t feel obliged to graze from every stand.
Finish at Chibo Dotonbori for Osaka-style okonomiyaki; budget about ¥1,500–3,000 per person, before drinks or extras. Ask what can be prepared simply and mildly, and explain any ingredients you need to avoid. With ulcerative colitis, recipes and tolerance vary: okonomiyaki commonly includes cabbage, sauces, and other mixed ingredients, and it may be cooked on a shared teppan. Confirm ingredients and cooking arrangements with staff, and choose only what feels safe for you.
Take the Osaka Metro to Osaka Castle Park and leave time to wander the grounds rather than rushing straight to the keep. The castle museum is an optional extra; check current access details and allow for queues if you decide to go inside. The broad park paths make this a good start to the day, but wear comfortable shoes and take breaks as needed.
Head north to Pokémon Center Osaka inside Daimaru Umeda. Allow about an hour or more for browsing and checkout; the store can be busy, so keep purchases together and leave some room in your bags. From Umeda, take the Midosuji Line to Shinsaibashi (roughly 10 minutes on the train, plus station walking). At PUNYUS, check the current range and try items on where possible: sizing varies by garment, so don’t assume a listed size will match US 20.
Continue south to Kuromon Ichiba Market in Namba, either on foot from Shinsaibashi or by a short Metro ride. Stall hours vary, and some vendors close earlier than shops, so browse before late evening. For ulcerative-colitis-friendly choices, ask about ingredients and preparation, and favor freshly cooked, mild food over raw, spicy, or heavily sauced dishes. Keep the day flexible for rest stops, and check current store hours before setting out.
Start at Osaka Castle Park; allow time to stroll the grounds and see the moat and stone walls. The tower is a separate indoor visit, so skip it if you’d rather keep the morning relaxed. From the park, take the subway toward Tenjinbashisuji Rokuchōme for the next stop.
The Osaka Museum of Housing and Living is a good rainy-day option, with reconstructed historical streets under a roof. Check its current opening days before setting out, as museums can close on particular weekdays or holidays. Afterward, wander Tenjinbashisuji Shopping Street and choose a simple cooked lunch—plain rice with grilled fish or chicken, or a mild noodle dish. Budget roughly ¥1,000–¥2,000 per person for a casual meal; ask about ingredients and sauces, and prioritize foods you know are comfortable with your ulcerative colitis.
Head to Umeda for Pokémon Center Osaka, inside Daimaru Umeda, then continue to Umeda Sky Building. Allow extra time for the observatory if there’s a queue, and check the current admission details before you go. The two Umeda stops are close enough to do on foot; from the arcade, use the subway or a taxi to reach Umeda. Keep the evening flexible for dinner near your hotel or in Umeda, with a familiar, mild option as a backup.
Make this a final full day in Osaka rather than a departure day; your return journey belongs on Day 7 of the accepted seven-day plan. Head to Pokémon Center Osaka inside Daimaru Umeda first, allowing about 60–90 minutes to browse and queue at checkout. Check the store’s current hours before you go, since hours and crowd arrangements can change.
From Umeda, take the Midosuji subway line to Shinsaibashi, then visit PUNYUS Osaka Shinsaibashi. Allow around an hour to look through the styles and check fit in person: sizing varies by garment, and a US 20 fit is not guaranteed by a size label alone. The subway ride is roughly 10 minutes, plus time to navigate the stations.
Continue south to Kuromon Ichiba Market in Namba, about 10–15 minutes on foot from Shinsaibashi or a short subway ride. Stall schedules vary, so arrive with time to browse; many vendors wind down later in the day. For ulcerative-colitis-friendly eating, ask what is freshly cooked and keep choices mild and familiar. Ingredients and preparation vary by stall, so check sauces and seasoning before ordering. A casual market snack or light meal might run about ¥1,000–2,500 per person, depending on what you choose.
If you still have energy, walk to Namba Yasaka Shrine for a brief look at its striking lion-head stage. It’s a calm, compact stop rather than a long sightseeing commitment. Return to the hotel afterward to rest and organize shopping; keep tomorrow’s airport transfer and flight logistics for the actual departure day.
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