Sailing the Gulf of Naples and Amalfi Coast in 5 Days:
A Real Itinerary
Most people who visit the Amalfi Coast see it from a bus window, inching along a road carved into the cliff. Beautiful, certainly. But there is another way — one that most visitors never consider.
This is the itinerary we sail with our guests. Not a theoretical route drawn on a map, but the actual 5-day journey we have refined over years of sailing these waters — shaped by the sea, the seasons, and the stories of more than 360 guests who have sailed with us.
We depart from Castellammare di Stabia, sail west to the islands of the Gulf of Naples, then east along the Amalfi Coast, returning in time for a final night in port before disembarkation. Every night is spent in port — giving guests the freedom to explore each destination on their own terms, have dinner ashore, and walk through the lanes of these extraordinary places after the day-trippers have gone.
Day 1 — Castellammare di Stabia to Procida: The Quiet Island
We cast off in the morning from Castellammare di Stabia, a working port with centuries of maritime history at the northern tip of the Sorrento Peninsula. This is not a tourist town — it is where real ships are built and where the sea is still a way of life. It is, for our guests, the perfect place to begin.
The sail to Procida takes a few hours, crossing the open Gulf with Vesuvius behind you and the islands ahead. Procida is the smallest of the three main islands in the Gulf of Naples and, for many of our guests, the most unexpected pleasure of the whole trip.
Marina Corricella — the old fishing harbour — is one of the most photographed places in southern Italy. The houses stacked above the water in shades of ochre, pink, lemon and terracotta look almost impossibly picturesque. But it is not a stage set: fishermen still mend their nets here, and the trattorias serve whatever came in that morning.
We arrive before sunset and moor in port. The evening is yours — walk up through the narrow lanes, have dinner ashore, and experience Procida as the Italians do: slowly, without a schedule.
Day 2 — Procida to Ischia: The Volcanic Island
Ischia is just a short sail from Procida — close enough to make an easy morning crossing, large enough to fill an entire day. This is the island where Italians themselves come to holiday, and it is easy to understand why.
Ischia is volcanic. The thermal springs here are not a wellness industry invention — they have been here for thousands of years, and the Romans knew about them. You can feel warm water rising from the seabed in certain anchorages, a strange and wonderful sensation.
The Aragonese Castle — a fortress built on a volcanic rock connected to the island by a stone bridge — is one of the most dramatic sights in the entire Gulf of Naples. It is best seen from the water: approach it slowly on the way into port and take your time.
We moor at Ischia Porto for the night. The town has a good selection of restaurants, bars, and gelaterias — your skipper will point you in the right direction based on what you are in the mood for.
Day 3 — Ischia to Capri: The Famous Island, Seen Properly
Capri needs no introduction. What it needs is the right approach — and arriving by private yacht, with the boat moored at Marina Grande as your base, is the right approach.
With a full day on the island, you have time to do Capri properly. The Blue Grotto is a genuine wonder — the light inside the cave is unlike anything else in the Mediterranean. The practical way to visit it is by the small passenger ferry that departs from Marina Grande every hour. This is how most visitors go, and it works well: while the boat is moored, guests take the ferry across, visit the grotto, and return. Your skipper will advise on timing based on the conditions that day.
The rest of the island is yours to explore. Capri town, the Gardens of Augustus, the chairlift up to Monte Solaro, the quieter streets of Anacapri — or simply sitting at a cafe watching the world's most glamorous foot traffic pass by. There is no wrong way to spend a day on Capri.
We moor at Marina Grande for the night. In the evening, when the day-trippers have left and the island returns to something closer to its real self, Capri is at its most beautiful.
Day 4 — Capri to Amalfi: Spaghetti, Swimming, and the Coast That Named Itself
The sail from Capri toward the Amalfi Coast rounds the tip of the Sorrento Peninsula — and the moment the coastline comes into view, most guests fall silent. There is nothing to say. The cliffs, the villages, the colour of the water — it is exactly as spectacular as everyone told you it would be.
Our first stop is Nerano, a small fishing village at the foot of the peninsula. Nerano is where spaghetti alla Nerano was invented — a simple dish of pasta, local zucchini, and provolone del Monaco cheese that has become one of the most imitated recipes in Italian cooking. We stop here for lunch at the restaurant that created it. It is one of those meals that guests still talk about months later.
After lunch we continue along the coast. If conditions are right, we stop at the Baia di Santa Croce — a beautiful bay near Amalfi — for a swim before entering the port.
We arrive in Amalfi in the afternoon. The town that gave this entire coast its name was once a maritime republic powerful enough to rival Venice and Genoa. Its cathedral is one of the finest examples of Arab-Norman architecture in Italy. The lanes behind the waterfront are worth an hour of wandering.
For dinner, if guests are open to it, we offer something special: a table at a small restaurant away from the tourist waterfront, where the food is simple and traditional, the wine is local and unfiltered, and the evening has a way of turning into something that feels less like a restaurant meal and more like being invited to dinner by someone who lives here.
Sometimes there is music — Neapolitan songs that guests end up singing along to by the end of the evening, whether or not they know the words. It is one of those experiences that cannot be booked in advance. It simply happens.
Day 5 — Amalfi to Positano and Home: The Last Morning
The final day is shorter than the others — and deliberately so. This is a morning to slow down.
We sail from Amalfi toward Positano, stopping on the way at the Baia di Tordigliano — a calm bay near Positano — for one last swim. The water here is clear and unhurried. Nobody is in a rush.
Then Positano. Few places in the world look the way Positano does — the houses cascading down the cliff in pinks and whites, the beach below, the whole village seeming to lean toward the sea. We moor on one of the designated buoys in the bay; the buoy operator runs a small boat service to take you ashore and bring you back whenever you are ready. The morning and early afternoon are yours to explore.
In the mid-afternoon we sail north for the last time, back to Castellammare di Stabia. The final night is spent in home port — practical for the check-out the following morning at 9, and somehow the right way to end a journey: returning to where it began, with five days of sea, islands, and coastline behind you.
Practical information
Best time to sail
May, June and September offer the best combination of warm weather, calm seas, and manageable crowds. July and August are beautiful but busy. April is ideal for guests who prefer a quieter, more intimate experience — the coast is still green, the light is extraordinary, and the ports feel like themselves again.
What to bring
- One soft bag per person — hard suitcases do not fit well in cabins
- Swimwear, sunscreen, and a light layer for evenings at sea
- Comfortable shoes for walking in port towns
- An appetite — the food on this coast is as good as the scenery
Meals on board and ashore
Our yachts have fully equipped galleys for cooking on board. But part of the pleasure of this itinerary is eating ashore — in port every night, your skipper recommends the right place for you based on your preferences, the time, and what is good that day. These are not tourist recommendations. They are the places a local would take you.
Why this is the best way to see the Amalfi Coast
One of our guests put it simply after a week on board:
"As we were sailing along, I couldn't help feeling sorry for the bus loads of people stuck in traffic on the twisty mountain roads looking down at us."
— Augustine, guest
The road has its own beauty. But this coast was designed to be seen from the water — the towns face the sea, the best swimming is from the water, and the scale and drama of the cliffs only makes sense when you are looking up at them from below.
Ready to sail?
We offer 2 to 7-day private sailing trips departing from Castellammare di Stabia, with overnight stays in port and an expert local skipper included. Our fleet includes three private yachts accommodating up to 8 guests.
With more than 360 five-star reviews on Airbnb, we are one of the most trusted sailing experiences in the Gulf of Naples and on the Amalfi Coast. Book directly with us for the best price and a personalised itinerary.
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