Operating since 1982, Humphrey's Concerts by the Bay in Point Loma stages 1,400-seat outdoor waterfront shows at Shelter Island from April through October each season. Past lineups have run from Aretha Franklin, Alice Cooper, and Tony Bennett to Jimmy Buffett and John Legend, with pre-show dinner packages booked at Humphreys SoCal Dining & Music inside the same waterfront compound. Seating is a tight plastic-chair grid at 1,400 capacity with VIP bar-stool rows in back, and blankets are permitted while umbrellas are not given the shoreline wind line. Arriving by water is a Shelter Island specialty, with boat and paddleboard access pulling right up to the venue alongside sunset charters from operators like Legacy Cruises and Events that stitch a harbor cruise into the pre-show window. Largest annual stretch covers the April-to-October concert season with comedy, blues, jazz, and rock national touring acts, plus the signature concert-and-stay packages that bundle Half Moon Inn rooms with ticketed seating at the adjacent outdoor stage.