Singapore keeps its wildest indulgence just offshore, where Sentosa’s resort coastline gives way to a scatter of quiet southern islands. This trip pairs private-island spa time with the city’s sharpest culinary edge.

A private sunset yacht charter threads through the Southern Islands for swimming and a champagne toast off St. John’s Island, followed by a guided heritage walk through Katong’s Peranakan shophouses with a local historian. Guests take a couples’ treatment at a destination spa built into Sentosa’s rainforest canopy and an evening omakase counter dinner secured through a personal concierge. A private car brings guests to a hidden speakeasy for a nightcap before returning to the resort.