
The Best Sailing Trips to Book This Year
Below is a hand-picked selection of sailing trips on adventuro, with a closer look at what makes each destination special.

Campania is the Amalfi Coast and Bay of Naples in adventure form — sailing, snorkelling, wild swimming and powerboating along southern Italy's iconic shore. Sail and powerboat between Capri, Positano and the Sorrento peninsula, snorkel crystal coves, and wild swim beneath cliffside villages. From gentle boat days to active coastal exploring, this celebrated stretch of South Italy is made for the water.
The Gulf of Naples has been captivating sailors for millennia, and it's not difficult to see why. Vesuvius smoking on the eastern horizon, the islands of Capri, Ischia and Procida rising from the Tyrrhenian Sea, the Amalfi Coast's extraordinary cliff-town panorama to the south — this is sailing in scenery that genuinely justifies the journey. It's also an extremely practical sailing base: well-equipped marinas at Naples, Ischia Porto and Capri, predictable summer wind patterns, and anchorages within comfortable day-sailing distance of each other.
The Gulf of Naples is the centrepiece — a wide, deep bay protected from the worst of Atlantic swell by the Sorrentine Peninsula to the south and bounded by the Phlegraean volcanic fields to the north-west. Three islands sit within reach of a morning sail from Naples: Procida, the quietest and most authentic (a steep, colourful fishing village with sheltered anchorages and relatively few visitors), is 15nm from Naples. Ischia, 30nm, is larger, more developed and has thermal springs accessible from the sea, a dramatic Aragonese castle and several good anchorages around its coastline. Capri, 20nm from Naples and 15nm from Sorrento, is the most famous and deservedly so — the Faraglioni rock stacks, the Blue Grotto, Marina Grande and the panoramic southern anchorage at Marina Piccola are all classic sailing destinations. Marinas and anchorages at Capri fill quickly in high summer; either book ahead or arrive early and depart before the charter flotillas. South of Sorrento, the Amalfi Coast unfolds over 40km of cliff face: Positano, Praiano, Amalfi town, Ravello's mountainside and Vietri sul Mare. The anchorages here are tight, the ferry traffic significant and the view from the water utterly exceptional. Positano's black-sand lido and the cove at Marina di Praia (Praiano) are the most comfortable overnight stops.
The Gulf of Naples is an excellent environment for practical coastal sailing courses. RYA Day Skipper practical courses in the Gulf give real-world experience: managing ferry traffic, fishing vessel avoidance, anchorage pilotage and navigation in a mix of open water and confined coastal passages. The tidal range in the Mediterranean is minimal (30–40cm), which simplifies pilotage considerably compared to UK waters — courses here focus more on weather, wind strategy and chart work rather than tidal calculations. Skippered charter experiences are available for those who want to learn informally rather than through formal qualification.
Skippered charters are the most popular option in Campania — local skippers know the anchorages, the afternoon wind windows and where the best swimming spots are at each island. A good Neapolitan skipper is worth considerably more than the GPS. Bareboat charter is available for qualified sailors (ICC or equivalent required in Italian waters). Day sailing experiences — a morning departure from Naples to Procida or Capri, lunch at anchor and return by late afternoon — are ideal for those who want to experience sailing in the Gulf without committing to a multi-day trip.
The summer sailing pattern in the Gulf of Naples is consistent: calm mornings, the Imbat (thermal sea breeze from the south-west) filling in by mid-morning and building to 10–18 knots through the afternoon, easing by sunset. This makes afternoon passages easy and predictable; mornings are best for motor-sailing to an anchorage before the breeze arrives. The Libeccio (south-westerly) is the main blow to watch out for — it can build quickly and makes the Amalfi Coast a lee shore in stronger conditions. The Tramontane from the north arrives occasionally in spring and autumn with force. May–October is the season; June and September are the least crowded months with consistently good conditions.


























Shared small-group boat tour from Sorrento to Capri from €125 pp. Coastal cruising, swim stops, free time on Capri, and limoncello tasting included.
From € 125

Luxury Conam 58 yacht trip from Capri with skipper, drinks, swimming stops, and flexible routes along the Amalfi Coast for small groups.
From € 4400

Sail the Amalfi Coast on a private boat from Sorrento, visiting Positano and Amalfi with swimming stops and free time ashore, from €1,000
From € 1000

Private luxury yacht trip from Positano, starting at €4,350 per boat. Swim, relax, and enjoy Amalfi Coast views in style.
From € 4350

A refined full-day private cruise along the Amalfi Coast or to Capri, with skipper, fuel, drinks and onboard comforts included, from €4400 depending on route.
From € 4400

Private sailing trip from Amalfi to Capri from €1,800 with swimming, snorkeling, and flexible itinerary along iconic coastal scenery
From € 1800

Cruise from Positano on a private Sparviero 700 boat, with swimming, snorkelling, and the choice of Capri, Amalfi, or both, tailored to your day on the water.
From € 1000

Experience a private Capri to Amalfi and Positano boat tour from €1,400 with swimming, snorkeling, and flexible, personalised stops along the Amalfi Coast
From € 1400

Experience a private full-day yacht charter aboard the Itama 38, cruising the Amalfi Coast or Capri with swimming stops, sun decks, onboard refreshments, and a professional skipper.
From € 1500

From Positano, enjoy a private luxury yacht charter with skipper, fuel, drinks and swim stops included, cruising towards Capri or Amalfi from €4,750 per boat.
From € 4750

Cruise from Capri to Positano from €1,000 on a private boat, swim, snorkel, and enjoy a fully customised coastal itinerary
From € 1000

Cruise the Capri coastline aboard the Jeranto 7.50 for a private, relaxing boat trip with swimming, snorkeling, and flexible shore stops from €900.
From € 900

Sail along the Amalfi Coast on a private boat from Amalfi, with swimming, snorkeling, and panoramic views from €1,100
From € 1100

Cruise from Capri aboard the Apreamare 35 from €2050 per boat. Swim, snorkel, and explore the Capri and Amalfi Coast with a professional skipper.
From € 2050

Cruise the Amalfi Coast by private boat from Amalfi aboard the Sparviero 700, with time to swim, relax on deck, and visit Positano at your own pace.
From € 1100

Spend a full day at sea on a private Raffaelli 37 from Sorrento, with flexible routes to Capri or the Amalfi Coast and prices from €1,400 per group.
From € 1400

Classic gozzo day trip from Amalfi with private skipper, swim stops, onboard drinks and flexible routing to Capri or Positano. From €1,600 per group.
From € 1600

Enjoy a private full-day yacht cruise from Capri aboard the Itama 38, with swimming, optional shore time, and professional skipper, from €1500.
From € 1500

Relax on a private Sparviero 700 boat tour from Sorrento, choosing stops like Capri, Positano, or Amalfi for swimming, snorkelling, and coastal views.
From € 850

Enjoy a private Apreamare 35 boat trip from Positano, with swimming, snorkelling, and a flexible route along the Amalfi Coast or Capri. From €2200 per boat.
From € 2200