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St. Maarten has lots of evening and late-night action. To find out what's doing on the island, pick up St. Maarten Nights or St. Maarten Events, both of which are distributed free in the tourist office and hotels. The glossy Discover St. Martin/St. Maarten magazine, also free, has articles on island history and on the newest shops, discos, and restaurants. Or buy a copy of Thursday's Daily Herald newspaper, which lists all the week's entertainment.
The island's casinos—all 13 of them—are found only on the Dutch side. All have craps, blackjack, roulette, and slot machines. You must be 18 years or older to gamble. Dress is casual (but excludes bathing suits or skimpy beachwear). Most casinos are found in hotels, but there are also some independents.
Sip a guavaberry colada and sample tapas with your chair pointed toward the boardwalk at this popular, genuinely Caribbean venue. There's free parking for patrons until midnight; enter on Back Street, and look for the Holland House banner.
This 1960s-style gallery and jazz café, which hosts cultural events, live music shows, and poetry readings doesn't close till 11 pm on Saturday (it's only open till 5 pm the rest of the week).
Locals and visitors alike gather at this bar–restaurant known for its relaxed, “come as you are” vibe. Some come to play board games, others come to party, and most don't stay seated for long owing to the music, a mix of all genres from the latest Caribbean tunes to French hits from the 2000s.
Live music on Wednesday and Sunday (when there's also a beach bonfire) and a daily happy hour from 5 to 7 make this spot popular with both travelers and locals, who also appreciate the beautiful sunsets, as well as the delicious frozen drinks, pizza, burgers, grilled fish. Its location—on Kim Sha Beach between the Atrium Beach and Simpson Bay resorts—is convenient, but parking can be a challenge. The bar's lot is small, and there are only a few on-street sites near the entrance.
St. Maarten's top-rated casino has more than 21,000 square feet of gaming space featuring tables, slot machines, a free tiered Players Club membership, a private high-roller section, a Sportsbook area with self-service kiosks, and a VIP Lounge. It also has the island's biggest theater, with free Vegas-style productions weekly.
This small casino with slots and a few table games is centrally located on Pelican Key, right across from Simpson Bay Resort. Isola Restaurant, a very busy and authentic Italian eatery that's part of the complex, serves excellent brick-oven pizzas, as well as more upscale offerings.
After dinner at Alina, climb the stairs to the rooftop Mimosa Skylounge, which offers 180-degree views of the Maho Reef area, artful concoctions prepared by expert mixologists, and music by renowned local and international DJs.
At this cozy, colorful, roadside hotspot close to the draw bridge in Simpson Bay, bartenders mix up tamarind sours, sour sop martinis, and other island cocktails, and the nightly live music guarantees a great time. Locals and visitors come together in a sea of happy faces and swaying hips, and Caribbean-style tapas like the oxtail bowl, mahi ceviche, goat meat triangle, and conch fritters keeps everyone fortified.
You can groove to nightly live music, shoot some pool, or play video games at this pair of restaurants.
One of the island's largest casinos has a wide array of gaming, dining, and entertainment options.
This very popular venue is particularly famous for its Church on Monday event featuring a local band followed by a DJ. There's live piano music other nights, as well as tasty cocktails, a pool table, and lots of red velvet all the time.
Completely redecorated in 2015 in a brilliant color scheme with new lighting, this attractive casino, anchored by some of the best restaurants on the Dutch side, is popular with gamblers and non-gamblers alike. It has high-tech video slot machines and gaming tables offering blackjack, roulette, three-card poker, and Caribbean poker. Sports fans will enjoy the Sports Bar surrounded by big-screen TVs.
A relaxed, anything-goes atmosphere prevails at this popular plane-spotting bar and restaurant near the ocean edge of the Princess Juliana International Airport runway. Watch big planes fly very low over your head while you enjoy a BBC (Bailey's banana colada) or a bucket of beers. Bring your camera for stunning photos. There's live music on Sunday and occasionally on weeknights. Note that drinks here can be quite pricey, and it's very busy when cruise ships are in port.
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