05/21/2026
This itinerary puts you at the centre of everything — within reach of volcanic islands, whitewashed fishing villages, ancient ruins, and hilltop towns — while returning each evening to one of the most elegant and well-connected towns on the southern Italian coast.
Getting There — Train from Naples to Sorrento
The journey begins at Naples Centrale, where the Circumvesuviana regional train winds its way south through the Bay of Naples, passing through Pompeii and Herculaneum before arriving in Sorrento roughly 70 minutes later.
Day 1 — Capri
A short ferry crossing from Sorrento's Marina Piccola delivers you to one of the most mythologised islands in the Mediterranean. Capri rewards those who resist the expensive shops of the Piazzetta and instead head uphill — to the Villa Jovis, Emperor Tiberius's clifftop palace, or along the paths to the Arco Naturale.
Day 2 — Positano
The ferry from Sorrento deposits you directly at Positano's small beach, sparing you the hairpin bus ride down from the main road. From the water, the town's cascade of pastel-coloured houses tumbling down the cliff face is simply one of the great views in Italy.
Day 3 — Amalfi & Ravello
The ferry east along the coast brings you to Amalfi itself — once a powerful maritime republic that rivalled Genoa and Venice, now a compact, bustling town built into a narrow gorge. The Cathedral of Sant'Andrea, with its striking Arab-Norman façade and striking striped campanile, dominates the main piazza.
From Amalfi, a short SITA bus climbs steeply inland to Ravello — a village perched 350 metres above the sea with a quiet, aristocratic beauty all its own. The gardens of Villa Cimbrone and Villa Rufolo offer some of the most celebrated views on the entire coast, and the town moves at an entirely different, unhurried pace to the resorts below.
Day 4 — Pompeii
A change of pace and a journey back nearly two millennia. The Circumvesuviana train from Sorrento stops directly at Pompeii Scavi, the excavation site entrance, making this one of the most accessible ancient sites in the world. Allow a full morning at minimum — Pompeii is vast, and its streets, bakeries, bathhouses, theatres, and preserved villas reward slow, unhurried exploration.
Day 5 — Sorrento
Save the best of Sorrento itself for last. The clifftop town well deserves a full day of its own — wander the old town's narrow lanes, browse the inlaid woodwork shops for which the town has been celebrated for centuries, and visit the Museo Correale di Terranova for its fine collection of decorative arts and sweeping views over the bay.
Check out my favorite stay in Sorrento in the first comment 👇
