Lana'i doesn't really have a very big nightlife. This is one of the smallest islands in the Hawaiian Island chain, and there aren't too many people living on the island. Tourists usually come to the island for a few days and then move on to other islands in the area, so there aren't really any incredible streets or places you need to go to for good bars and clubs. Lana'i City isn't much of a city. There aren't any huge discos or other places to get crazy. However, there are a few bars on the island that you can go to if you want to get a drink. Also, because there are a lot of large resorts and hotels now popping up on the island, you can usually head to those places for live entertainment and drinks. The resorts will usually have things planned out for the night time, and at the very least there will be a house band playing in a lounge. Drinks in resorts and hotels can often be pretty expensive, but you really don't have many other options. A lot of tourists like to just hang out down by the beach and have a drink or two in the sand while looking up at the stars. If you really want some nightlife in Hawaii, you will have to head to the bigger islands and cities. This is an island for relaxation.