Start at Shinjuku Gyoen National Garden around 10:00, allowing roughly 1½ hours for an easy walk through the Japanese, English Landscape, and French Formal gardens. In August, go early to avoid the strongest heat, bring water, and use the shaded paths and benches for breaks. Admission is typically around ¥500; check the official site before leaving, as the garden is generally closed on Mondays and may adjust hours for special circumstances.
From Shinjuku Gyoen, take the Marunouchi Line from Shinjuku-gyoemmae toward Tsukiji Outer Market—about 30–35 minutes including the walk and transfer—or use a taxi if you prefer door-to-door comfort in the heat. Spend about two hours browsing the narrow lanes and choosing a casual seafood lunch, budgeting ¥2,000–¥4,000 per person. Many stalls close once they sell out, so arrive by roughly 12:30–1:00 p.m.; eat in the designated areas rather than walking with food. Continue by taxi or the Hibiya Line toward teamLab Borderless at Azabudai Hills, allowing around 25–35 minutes. Timed tickets are essential, and comfortable shoes are useful because the dark, immersive rooms involve plenty of standing and walking; allow two hours inside.
Take a short taxi ride from Azabudai Hills to Tokyo Tower, ideally arriving about an hour before sunset so you can see the city brighten and then glow after dark. The main observation deck usually costs roughly ¥1,200–¥2,000 depending on the ticket option; check the day’s sunset time and reserve ahead if possible. For dinner, continue to Sukiyabashi Jiro Roppongi by taxi, or use the nearby subway if timing is relaxed. This is a formal, intimate omakase experience rather than a drop-in restaurant: confirm the reservation and dress neatly, and expect ¥40,000 or more per person before drinks. After dinner, return to your Shinjuku hotel by taxi—particularly convenient late at night—and choose a reputable property with a private, comfortable room, clear guest policies, and a front desk that can assist discreetly. Both partners should be adults, consenting, and comfortable with the hotel’s rules; bring identification for check-in.