Five days strikes the perfect balance for a first Tokyo visit — enough to feel the city's scale and variety without the exhaustion that comes from trying to see everything. This itinerary is organized to minimize backtracking and maximize neighborhood character.
Day 1: East Tokyo — Asakusa, Skytree, Ueno
Start where Tokyo feels oldest. Senso-ji before 8am for a quiet approach through Nakamise. Walk to the Tokyo Skytree (book observation deck in advance, ¥2,100) — best mid-morning before afternoon haze. Lunch at the Solamachi food floor beneath the tower. Afternoon walk to Ueno Park: Tokyo National Museum if you have 2 hours, or a gentle circuit of the park's ponds and shrines. Evening: Asakusa's back streets for izakaya dinner (the alleys east of Senso-ji are excellent).
Day 2: West Tokyo — Harajuku, Shibuya, Shimokitazawa
Morning: Meiji Jingu shrine in its forest (free). Walk south through Harajuku Takeshita Street for teen culture and crepes. Omotesando architecture walk. Afternoon: Shibuya Crossing experience + Shibuya Stream riverside walk. Early evening: 20-minute train to Shimokitazawa for vintage shopping and live music dinner.
Day 3: North and Central — Akihabara, Yanaka, Ginza
Morning: Yanaka neighborhood — the old shitamachi Tokyo of temples, cats, and shotengai shopping streets. Lunch at a neighborhood soba restaurant. Afternoon: Akihabara for electronics, retro gaming, and the visual spectacle of Japan's tech culture. Early evening: walk west to Ginza for window shopping and Tsukiji Outer Market nearby for dinner (some stalls serve until 7pm).
Day 4: Day Trip to Kamakura
55 minutes by JR from Tokyo Station to Kamakura (¥920). The Great Buddha (Kotoku-in, ¥300) is extraordinary up close — 11 meters of bronze, the interior accessible. Cliff-carved Hase-dera Temple with ocean views (¥400). Walk the Daibutsu Hiking Trail through forested hills connecting multiple temples. Return via Enoshima Island (electric cat tram, ¥260) for sunset and seafood dinner.
Day 5: Shinjuku Deep Dive
Shinjuku deserves a full day. Morning: Shinjuku Gyoen (¥500, exceptional garden, open from 9am). Lunch in one of the shotengai food alleys south of the station. Afternoon: Isetan department store (basement food hall, flagship fashion floors). Dusk: Golden Gai (labyrinthine bar alleys) for early drinks. Dinner at one of the standing yakitori bars under the tracks in Yurakucho (10 min by train, worth the move). Final night: Omoide Yokocho (Memory Lane) for grilled skewers and beer under the railway tracks.