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One curious thing about Bermuda - the crowds on Friday nights are older than in North America. When you feel like you're the oldest person in the bar when you're in Toronto or NYC, a person in their mid thirties can feel at home at a number of bars along the Front St. strip.
In the summer (May - October), Friday nights are Bermuda's official party night. Starting right from work, the Hamilton Princess Hotel has an unforgettable Happy Hour. Other venues, like the Lemon Tree and Pier 6, attempt to compete, with varying degrees of success. Pier 6 won't likely last, but Lemon Tree has a smaller, more intimate vibe. Due to the limited size of the outdoor patio, they often spread out into the park behind the patio.
Back to the Hamilton Princess (aka "The H-P"), expect to see a broad cross section of Bermuda's locals, expats, and the occasional tourist. This is the place to be seen, and also the place to go to see what crazy fashion is big with the local girls at any given time. Drinks are 4 for $20, or $6 for one. They use the ticket system, and the tickets can be used the following week if you buy too many. The beginning of the summer is the best time for the HP, because most people take vacations away from Bermuda during the summer, and the number of people gradually dwindles. The party gets going by 6pm, and although I've never seen them turn people away, if you're looking for a good place to stand, get there before 7. Things keep going with a DJ, and often some Gombey dancers, until about 9, or sundown. Most people take the opportunity to grab a relaxed dinner at one of the many great restaurants in town before heading out for the later night festivities.
For those who have already eaten, a good mid-evening (9-11) venue is the Pickled Onion. A good casual restaurant by day, they have a live entertainment duo (that unfortunately play the same songs every week). This wont be a problem if you're just visiting Bermuda for a week, but for those of us local to the place, it gets a little tired.
By 11, it's time to start thinking about Cafe Cairo, one of the two busy late night venues. Cafe Cairo is a good egyptian / middle-eastern restaurant, Bermuda's only restaurant of this type. But it starts filling up around 11, when they take away the tables in the main room, and turn it into Bermuda's hottest dancefloor. Be prepared to sweat a few pounds off, whether you dance or not. The music is current pop/dance, with some middle eastern dance music thrown in to remind you of where you are.
Another option is Splash, which has a more "urban" music mix, and is popular with the locals.
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