The New Otani Tower Cafe, Trader Vic's
Many of us can't afford to actually stay at Akasaka's The New Otani, but at least we can drink there. That's because the hotel's 40th floor Tower Cafe puts on a daily happy hour from 5-7PM which starts at 1000 yen for a drink. That may sound pricey but this is The New Otani we're talking about. Non-happy hour cocktails here start at around 1800 yen, so it's a big discount.
You can choose your two (or more) drinks from a list that includes plenty of classics like the Daiquiri, Mojito, Manhattan, and Jack Rose. It's a nice value in one of Tokyo's most iconic hotels.
If you're feeling a bit more tropical, head down to The New Otani's Trader Vic's instead. The happy hour there includes tiki classics like the Mai Tai and Pina Colada for 1000 yen each from 5-7:30PM.