Simpson Bay Marina anchors the Dutch side of St. Maarten, a 37-square-kilometre island divided between the Kingdom of the Netherlands and the French Republic since the 1648 Treaty of Concordia. The lagoon here is the Caribbean's largest inland body of water accessible by drawbridge, sheltering a fleet of catamarans and trimarans that depart for evening cruises three nights each week. The industry emerged in the early 1990s when Princess Juliana International Airport brought direct flights from North America, transforming a quiet Dutch colonial outpost into a dual-nation cruise hub. By 2005, more than forty sailing vessels operated from Simpson Bay, offering everything from bareboat charters to crewed sunset voyages with onboard dining. The St Maarten dinner cruise experience centres on the golden hour between 16:30 and 19:00, when the sun descends over Marigot Bay and the silhouette of Anguilla emerges on the northern horizon. Most operators serve prosecco or rum punch alongside Caribbean appetizers—conch fritters, plantain chips, jerk chicken skewers—while the vessel tracks westward past Maho Beach, where arriving jetliners descend within metres of sunbathers. The route typically skirts the French-Dutch border, unmarked on the water, before circling back through Mullet Bay. Hurricane Irma in 2017 temporarily halted operations, but by late 2018 the majority of the fleet had returned, with newer catamarans replacing older monohulls. The marina itself underwent a two-million-dollar refurbishment in 2019, adding floating docks and upgraded check-in facilities at berth 37 on Billy Folly Road. Today's St Maarten dinner cruise tours depart from a marina that processes over fifteen thousand passengers monthly during high season. The standard sunset sail lasts two to two-and-a-half hours, though extended dining charters can run until 21:00. Operators favour twin-hulled catamarans for stability and deck space, with trampolines stretched between the bows where passengers recline as the vessel heels into the trade winds. The business model relies on repeat cruise-ship passengers who allocate one evening ashore; operators bundle transportation from Philipsburg and Marigot, though independent travellers who arrive by rental car receive the same per-person rate of forty-five dollars for a standard sunset cruise. Dinner upgrades—lobster, grilled mahi-mahi, three-course plated service—vary by operator and vessel class, with prices climbing to seventy or ninety dollars depending on the menu and whether the boat is a forty-foot performance cat or a sixty-foot luxury trimaran.