Simpson Bay's marina berths more than 120 yachts, yet fewer than a dozen vessels hold permits for commercial sunset departures under Dutch-side maritime law. The Lambada catamaran, a 65-foot twin-hulled sailboat, has anchored at the Simpson Bay Resort Marina since 2014, and its Thursday and Saturday departures have become a fixture of the island's evening waterfront. St Maarten's position at 18°N latitude delivers consistent trade winds between November and July, making wind-powered sailing reliable where engine-driven tours dominate elsewhere in the Leeward Islands. The island's sunset infrastructure reflects its dual-nation geography. Dutch St Maarten operates the southern marinas, while French Saint-Martin administers the northern anchorages at Marigot and Grand Case. Simpson Bay, straddling the border zone, became the logical hub for commercial sailing after the 2017 hurricane season forced fleet consolidation. Catamarans and trimarans replaced older monohull designs because their shallow drafts navigate the bay's coral-studded channels without engine reliance. The open bar model—rum punch, Carib beer, prosecco—emerged as standard across Caribbean sunset sails in the early 2010s, and St Maarten operators adopted it to compete with neighboring Anguilla and St Barts. Sunset timing varies by season. June through August sees the sun drop behind Saba's volcanic silhouette at approximately 18:50, while December and January push the event to 17:30. Operators schedule departures 90 minutes before astronomical sunset to allow offshore positioning. The three-hour format accommodates outbound sail, a stationary viewing interval, and return transit under twilight. Snorkeling add-ons, offered on select trimaran departures, target the coral beds northeast of Pelican Key, where visibility peaks in late afternoon when ferry traffic subsides. The Dutch-side sailing permit system limits fleet size to prevent anchorage congestion, so advance reservation became necessary by 2019. Operators cap passenger loads at 24 to 30 depending on vessel certification. The $45 baseline price—consistent since 2022—includes the open bar and light snacks but excludes gratuity and port fees. Luxury variants with plated lunches or private charters command premiums above $120 per passenger. All commercial sunset sails depart from the same Simpson Bay Resort Marina dock, a narrow concrete pier accessible via Union Road from the airport corridor.