The sweet spots are May to mid-June and September to early October, when the weather is warm, the sea is swimmable, and the crowds are thinner than the July-August peak. High summer is gorgeous but hot, packed, and expensive, with beaches and restaurants fully booked; midsummer heat regularly hits the low 30s Celsius (upper 80s to low 90s Fahrenheit). Many hotels and restaurants close from roughly November through March, so the shoulder seasons give you the best balance. Time a visit around the Feast of Santa Maria Assunta on August 15 for fireworks and a historic beach procession if you don't mind the crowds.

The nearest airport is Naples (NAP), about 60 to 90 minutes away by car. From Naples you can take a private transfer, hire a driver, or ride the Circumvesuviana train to Sorrento then a SITA bus or ferry onward. In peak season the fastest and most pleasant approach is by ferry from Sorrento, Amalfi, or Salerno, which drops you right at the beach and skips the notorious coastal-road traffic. Within Positano you walk, and you walk down: the town is a network of steep staircases, so pack light and wear real shoes. A small orange local bus loops the one-way ring road between the upper town and the beach for about 1.50 euros; taxis and the internal shuttle help with luggage.