Positano is the most vertical town in Italy. Every navigation decision is either up or down. Taxis go on the one road — the SS163 — and everything else is stairs. This is not a complaint; it's the operating condition. Once you accept that you will walk many stairs every day, the town becomes a different thing than it looks like in photographs.
Getting there
We came from Venice via the Frecciarossa to Rome (Executive class — eight seats in the front cabin, 2×2 configuration, worth the premium for a four-hour train with four people) and then Sorrento Limo from Rome to Positano. ~$850 round trip for a private transfer, air conditioned van, no navigation stress on the Amalfi Coast road in June. Do not rent a car for the Amalfi leg unless you specifically want to drive the SS163. The road is narrow, the tour buses are wide, and Positano has almost no parking.
The hotel decision
Full analysis in the Alcione vs. Sirenuse piece. Short version: Alcione is a two-bedroom apartment with a sea-view terrace on Via Cristoforo Colombo, five minutes from Le Sirenuse. No pool, no room service, no concierge. The terrace overlooks the bay and the cathedral dome. We had breakfast there every morning. Nobody missed the pool because we were at sea by 8:30am on the boat days.
The boat days
Day two: private boat to Capri. $1,950 for eight hours, captain included. Left at 8:30am, ahead of the tour boat wave. Li Galli swim stop on the way. Faraglioni before the crowds. Capri Town for two hours — funicular, Via Camerelle, Gardens of Augustus. Lunch on the boat in a cove. Back in Positano by 5:30pm. Full playbook in the Capri day trip piece.
Day one afternoon: boat run to Lo Scoglio on the Sorrentine Peninsula. Lo Scoglio is a restaurant built on a pier over the water in Marina del Cantone, accessible only by boat or a very long drive. The zucchine alla scapece (fried zucchini marinated in vinegar and mint, a signature of the Cammarota family who has run the place for sixty years) is one of those dishes that makes you rethink what simple cooking can do. Call well ahead for a table and confirm boat-accessible arrival with the restaurant.
The dinners
Three nights, three registers. Da Gabrisa on arrival — easy, honest, local. Da Vincenzo for the serious Positano food night. Il Ritrovo in Montepertuso for the destination dinner. Full breakdown in the dinner playbook.
Alcione Residence books through Airbnb and occasionally Booking. Check availability 4–5 months out for June dates.
Positano Accommodation