After-dark activities begin early here, as guests start off with a sundowner, perhaps on the garden patio of Pasanggrahan Royal Inn. The most popular bar on the island is Cheri's Café.
Many hotels sponsor beachside barbecues (particularly in season) with steel bands, native music, and folk dancing. Outsiders are welcomed at most of these events, but call ahead to see if it's a private affair.
The Casino Royale, at the Maho Beach Hotel on Maho Bay (tel. 599/54-52115), has 16 blackjack tables, 6 roulette wheels, and 3 craps and 3 Caribbean stud-poker tables. The casino offers baccarat, mini-baccarat, and more than 340 slot machines. It's open daily from 2pm to 4am. The Casino Royale Cabaret Theater is the largest and most technologically sophisticated theater on either side of St Maarten/St. Martin; its glittery shows change according to whatever act has been booked. Within the same building is the island's loudest disco, the Q-Club. Containing wraparound catwalks that look down on the dance floor, multiple bars, and colored lights it's open nightly from around 10pm, attracting dancers from both sides of the island. A cover charge of between $5 and $10 is sometimes imposed, depending on the season and the night of the week.
One of the island's most visited casinos, the Dolphin, is at The Caravanserai on Beacon Hill Rd. (tel. 599/54-54000). Gamblers start pouring in here at 2pm daily, some staying until 4 the next morning.
Sunset Beach Bar, 2 Beacon Hill Rd., Airport Beach (tel. 599/54-53998), is directly on the sands of airport beach, and resembles an oversize gazebo. This place is mobbed most afternoons and evenings with office workers, off-duty airline pilots, beach people, and occasional celebs like Sandra Bullock. No one seems to mind the whine of airplane engines overhead, or the fumes that filter down from aircraft that seem to fly at precarious altitudes just a few dozen feet overhead. Drinks are cheap, and you can order burgers, sandwiches, steaks, fish, chicken, and hot dogs from an outdoor charcoal grill. Many local residents time their arrival here for sundown (usually beginning around 6:30pm), when "shooters of the day," cost only $1 each.
At the previously recommended The Boathouse, 74 Airport Rd. (tel. 599/54-45409), you get not only good food and drinks but entertainment as well. Live bands play most Fridays after 11pm.
Pelican Resort Club, Simpson Bay (tel. 599/54-42503), has a popular Vegas-style casino with a panoramic view of the bay. It offers 2 craps tables, 3 roulette tables, 9 blackjack tables, 2 stud-poker tables, and 120 slot machines. The Pelican also features horse racing, bingo, and sports nights with events broadcast via satellite, plus nightly dancing on the Pelican Reef Terrace and island shows featuring Caribbean bands. It's open daily from 2pm to 4am.
Indiana Beach Restaurant & Bar and Indy's Bar, Kimshore, Simpson Bay (tel. 599/54-42797), are immediately adjacent to one another and set beside the sands of Simpson's Bay. They jointly reign as queen (or king) of the night every Thursday after 8:30pm, when they're mobbed with singles, who enjoy the two-for-one frozen margaritas after 10pm. The decor combines aspects of Harrison Ford's Indiana Jones and the Temple of Doom (theme-ish looking flaming torches, statues of Polynesian demigods, caged alligators, and so on) with thatch-covered bohios set directly on the sands of the beach. If you want a full-fledged meal, Indiana Beach serves lunch and dinner daily.
Right in the heart of Philipsburg's shopping-crazed Front Street, Rouge et Noir (tel. 599/54-22952) has a futuristic design. It offers slot machines, a Sigma Derby horse machine, video Keno, and video poker. It opens Monday to Saturday at 9am and Sunday at 11am to snag cruise-ship passengers.
On the French side, in the heart of Grand-Case, Portofino, bd. de Grand-Case (tel. 590/29-08-28), is a lot of fun. A few nights a week, there's live rock and roll and country-western music, with a French accent, between 9pm and 1am. There's no cover charge, and the cross-cultural pollination is charming. A menu lists all kinds of pizzas and pastas.
Also in Grand-Case, Calmos Café, blvd. du Grand-Case no. 4 (tel. 590/29-01-85), is funky and low-key. This beachfront shack draws a young, hip crowd, with an occasional pop icon like Linda Evangelista dropping in. Management posts a sign that says "no snobs" near the entrance. In winter, there's sometimes live music after 9:30pm. Most people come just to flirt, gossip, and drink, but there's also good, affordable food, such as a Greek salad, a tuna salad, and "New Wave burgers" that are slathered with goat cheese. There is also jazz and lounge music to accompany your food. Also popular is an Ocean Salad, combining salad greens with three kinds of grilled fish plus shrimp. The house special drink is a Ti Punch that's a local variation on an old-fashioned rum punch. It's open daily from 10am to 1am.