A trip to the beach should be carefree — that said, how you dress and pack for it can make or break the day. Here, recommendations on both fronts from five seasoned beachgoers: Brooke Williams, 60, is a creative adviser, editor, artist and activist who divides her beach time between the East End of Long Island and Maine’s Penobscot Bay. Sophia Moreno-Bunge, 39, a florist and the founder of Isa Isa Floral Studio, lives in Santa Monica, Calif. Matthew Williamson, 54, a Mallorca-based interior designer, spends most weekends at Cala Deià, a cove in the island’s northwest. Marie-Louise Sciò, 49, is the chief executive and creative director of Pellicano Hotels, whose three current properties are set along the Italian coastline. And Sheldon Simeon, 43, a Hawaii-based chef, can often be found at Maui’s Ulua Beach.