Bring a good book. When it comes to nightlife, St. John is no St. Thomas, and everybody here seems to want to keep it that way. Most people are content to have a leisurely dinner and then head to bed.
The Caneel Bay Bar, at the Caneel Bay resort (tel. 340/776-6111), has live music Tuesday to Sunday 8:30 to 10:30pm. The most popular drinks are the Cool Caneel (local rum with sugar, lime, and anisette) and the trademark Plantation Punch (lime and orange juice with three different kinds of rum, bitters, and nutmeg).
If you'd like to drink and gossip with the locals, try JJ's Texas Coast Café, Cruz Bay (tel. 340/776-6908), a real dive, across the park from the ferry dock, open 8am to 9pm. The margaritas here are lethal. Also at Cruz Bay, check out the action at Fred's (tel. 340/776-6363), across from the Lime Inn. Fred's brings in bands and has dancing on Friday nights. It's just a little hole-in-the-wall and can get crowded fast. It's open 8am to 7pm, but stays open until Saturday morning.
St. John's best sports bar is Skinny Legs, Emmaus, Coral Bay, beyond the fire station (tel. 340/779-4982). This shack made of tin and wood also happens to have the best burgers in St. John. (The chili dogs aren't bad, either.) The yachting crowd likes to hang out here, though you wouldn't know it at first glance -- it often seems that the richer they are, the poorer they dress. The bar has a satellite dish, dartboard, and horseshoe pits. There is live music on Friday and Saturday nights during high season when it stays open until midnight; regular hours are 11am to 9pm.
Morgan's Mango (tel. 340/693-8141), a restaurant, is also one of the hottest watering holes on the island. It's in Cruz Bay, across from the national park dock. Count yourself lucky if you get in on a crowded night in winter. The place became famous locally when it turned away Harrison Ford, who was vacationing at Caneel Bay. Thursday night is Margarita Night, and Tuesday night is Lobster Night.
Woody's Seafood Saloon, Cruz Bay (tel. 340/779-4625), is the previously recommended local dive and hangout at Cruz Bay, 50 yards from the ferry dock. It draws both visitors and a cross-section of island life from expats to villa owners. Michigan-born Woody Mann, the bartender, is often compared to the character of the same name on the sitcom Cheers. The place is particularly popular during happy hour from 3 to 6pm and it's about the only place on the island you can order food as late as 1am. The joint jumps Sunday to Thursday 11am to 1am, Friday and Saturday 11:50am to 2am.
Of course, there is also The Quiet Mon, which is adjacent to Woody's. This is St. John's very own Irish pub and one of the hottest spots on the island.
