Few excursions in St. Maarten move through history, elevation, and gastronomy in the same afternoon. Rockland Estate's plantation house, built in the 1700s, tells the story of Trace Wilson, and the descendant Emilio Wilson, who later purchased it to preserve that history for future generations. The tour picks up momentum at The Sky Explorer chairlift, a 25-minute ascent to Sentry Hill at 1,125 feet, where 360-degree views extend across the island and out to neighboring Saba, St. Barts, and Anguilla. The afternoon finishes around the table at Emilio's, where the chef leads the group through a four-course gourmet tasting lunch designed around the flavors of St. Maarten.