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 for bed.
The Caneel Bay Bar, at the Caneel Bay resort (tel. 340/776-6111), presents live music nightly from 8 to 11pm. The most popular drinks here include the Cool Caneel (local rum with sugar, lime, and anisette) and the trademark of the house, the Plantation Punch (lime and orange juice with three different kinds of rum, bitters, and nutmeg).
However, the Caneel Bay Bar is very touristy. 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. 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 Wednesday and Friday nights. It's just a little hole-in-the-wall and can get crowded fast.
The best sports bar on the island is Skinny Legs, Emmaus, Coral Bay, beyond the fire station (tel. 340/779-4982). This shack made of tin and wood 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. Live music is presented on Saturday night.
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 is Margarita 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 ex-pats to villa owners. Michigan-born Woody Mann, the bartender, is often compared to the character of the same name on the sitcom Cheers. You can come here to eat or drink. The place is particularly popular during happy hour from 3 to 6pm. It's about the only place on island you can order food at 10pm. The joint jumps Sunday through Thursday from 11:50am to 1am, Friday and Saturday from 11:50am to 2am.