Check in to the Raleigh Hotel (raleighhotel.com), a style icon since 1940. Its pool has been the backdrop for movies and hosts Miami Fashion Week runway shows in July.
At Pubbelly Sushi (pubbellysushi.com) no dish costs more than $15. Sit at the bar to see itamaes (cooks) roll your yellowtail with green soy paper and snowcrab nori flakes.
Make your way down Collins Avenue to the glam Fontainebleau Hotel (fontainebleau.com) for a coconut Key lime pie donut and coffee at SOLO. Back at the Raleigh, cabana boys will equip you with chaise longues and plush beach towels for a day on the beach.
At The James Royal Palm's Florida Cookery (florida-cookery.com), dinner entrées run $30, but lunch costs half that. Try chef Kris Wessel's empanadas stuffed with alligator, oxtail, and oyster. For dinner, order prosciutto-and-salami sandwiches to go at French bistro La Sandwicherie (lasandwicherie.com) and take a blanket to the lawn of the New World Symphony Center. Have a nightcap at The Broken Shaker (thefreehand.com), a bar in the hip Freehand hostel. No $20 watered-down cosmos here—try a King James: rum, toasted Thai coconut milk, and house-made pineapple-and-coffee bitters.
Wake up with a cortadito ($1.25)—equal parts espresso and milk—and a pastelito (90 cents) at the cash-only Las Olas Cafe (305/534-9333). Stroll down Lincoln Road, and browse the Alchemist (shopalchemist.com), where the high-concept fashion exceeds mosts budgets but looking costs nada.