Especially in a major city. Usually I’ll pick a place based on one event/location then figure out the rest once I’m there. Then I typically talk to locals, service workers and general internet to find more interesting things to do. What about all of you?
Not at all…
One of the best nights out in my life was in Havana. My now wife and I booked a fancy holiday shortly after my dad died. Anyway we’re in this ridiculously fancy hotel in the centre of the city in our mid twenties and it’s not our vibe at all, so we get chatting with the barman and explain this to him and ask him where’s good. He understands perfectly what we’re after.
He directs us to a tiny jazz club in a basement in a slightly dingier part of town but within walking distance, tells us not to order individual drinks, to get a bottle of rum and make sure it arrives unopened then just buy mixers.
Place was fucking amazing. Only one other foreigner there, a nice french lady who was dating a local. By 10pm you could barely move. When the band ended the DJ started. Lots of the locals were keen to practice their English so we had a blast chatting all night.
Edit: I see your other comment about Chesapeake bay and that makes more sense but in a city insider knowledge is far more valuable and more likely to get you a gem that you otherwise wouldn’t have.