I wake in my darkened room ($164) at La Rosa dei Venti (40 Via Fornillo; 39-089/875-252; larosadeiventi.net), in Positano. It feels like midnight until I crack open the wooden doors leading to the terrace and the sun floods in. My room at the small inn is simple and breezy: blue ceramic tiles line the floor; the only decoration, hung above the wide, comfortable bed, is an austere Byzantine-style Madonna and Child. Honeymoon suite, this is not.
The innkeeper arrives bearing a breakfast tray (no extra charge) with a cappuccino, croissants, and a collection of jams, which she serves on my flower-filled terrace. This private perch, high on the quiet Fornillo side of Positano, overlooks the town's rugged cliffs and harbor. I nibble at a croissant and consider my good luck.
You can't get anywhere in Positano without taking a few stairs. The route down to the Fornillo beach involves some 400 steps, past white stucco houses covered in honeysuckle and bougainvillea. The black sand is covered with colorful umbrellas and brown bikinied bodies reading Oggi, an Italian gossip magazine. I could have my own chair for $9.50, but the water at this public beach seems rather oily and uninviting. Instead, I stroll toward the end of the strip, slip through a passage carved into the rock, and wind up in a small cove. Here, the water is clear. I shed my cover-up and dive in.
The stores lining the narrow stone streets of Positano are chockablock with ceramics, sundresses, and custom-made leather sandals. At La Botteguccia da Giovanni (Via T. Genoino; 39-089/ 811-824), a cobbler pieces together a pair of white thongs from buttery-soft leather. Around the corner there's yet another enticement at the stylish gelateria Il Vicoletto (41-43 Via del Saracino; 39-089/811-915), where I get two scoops of creamy hazelnut gelato ($3.40).
The town of Amalfi is just a 25-minute hydrofoil ride from Positano, but the water is choppy, so the boats are not running this afternoon. I pick up a SITA bus ticket ($1.80) at the tabaccheria (Piazza dei Mulini). The cliff-hugging, 40-minute drive has magnificent views of the private coves and terraced gardens that pepper the coast. Our bus driver handles the hairpin twists of the narrow mountain roads with Formula 1 aplomb. His only concession to blind turns: a disconcertingly light touch on the horn.
Safely in Amalfi, I grab lunch ($13.60)—a pancetta-and-mushroom pizza and a glass of house white wine—at Trattoria e Pizzeria da Memé (8 Salita Marino Sebaste; 39-089/830-4549). Afterward, I follow the town's whitewashed alleyways higher and higher, until I reach the ancient Via Annunziatella, where the panorama of the Valley of Mills (Amalfi is famous for its paper industry) is breathtaking.
The hydrofoils are running again, so I hop on the TravelMar ferry ($7.50). When we reach Positano, I drop by Bar la Zagara (8/10 Via Mulini; 39-089/ 875-964) for a pick-me-up caffè freddo ($2), a shot of sweet iced espresso.
Showered and changed, I'm off to the Champagne Bar at Le Sirenuse (30 Via C. Colombo; 39-089/875-066; sirenuse.it), a private villa turned ultrafashionable cliffside hotel. The sound track on the terrace bar is Edith Piaf; the clientele are glamorously tanned, white linen-wearing couples. I order a glass of Prosecco ($15) and watch the sun set.
It's a general rule in many seaside resort towns that the quality of a meal is inversely proportional to the restaurant's location. La Cambusa (5 Piazza A. Vespucci; 39-089/875-432), enviably set in the town center on a terrace with water views, proves the glorious exception. I start my dinner ($45) with a glass of Ravello Rosso and a salad of arugula, tomatoes, and mozzarella, followed by the spaghetti alle cozze (mussels). I know the tiramisu will push me over budget, but after climbing nearly 1,000 stairs, I deserve the treat.
Total spent: $252.30