Sailing Tours & Trips in South Italy
4.6 stars on(9,265 reviews)- Choose from 14 South Italy tours
- 6 verified reviews from TourRadar travelers
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10 best sailing South Italy tours
Compiled by
MelissaSouth Italy travel expert at TourRadar
- Amalfi Coast Sailing Adventure
- Aeolian Islands Cruise in Gulet 2026
- A week on board a fantastic motor boat in the Gulf of Naples between the Amalfi and Sorrento coasts
- Enchanting Italian Coastlines
- Amalfi Coast by Luxury Sailing Boat - Walking with the Gods
- Yachting Sicily to Elba via the Amalfi Coast
- Delicious Amalfi Coast - Luxury Sailing Catamaran ALL INCLUSIVE
- Following Ulysses - Luxury Sailing Boat ALL INCLUSIVE
- Pride Sailing in Sicily
- Med Sailing in Sicily
Duration 7 days Destinations Procida, Ischia, Benvenuto, Naples, Sorrento, Mount Vesuvius, Pompeii, Amalfi, Capri, AnacapriSee all destinations Age Range Ages 15+ Operator Intrepid Travel From
- NZ$4,560+$181 local payments
Aeolian Islands Cruise in Gulet 2026
1 Review by TourRadar travelers“Food, itinerary, crew were excellent. Had a lovely time.”
Jacqueline, traveled in July
A 26-meter traditional gulet awaits in South Italy's volcanic paradise. Professional crew leads visits to Stromboli's active crater, Panarea's ancient ruins, and Filicudi's sea caves, with snorkeling equipment provided for underwater exploration.
Duration 8 days Destinations Milazzo, Stromboli, Panarea Island, Lipari, Filicudi Island, Salina, Vulcano Age Range Ages 6+ Operated in English, German, Italian, French, Spanish Operator Dimensione Sicilia - Dimsi Incoming Operator Srl From
- NZ$3,774
Duration 7 days Destinations Forio, Procida, Capri, Sorrento, Nerano, Positano, Amalfi, Vietri sul Mare, Ischia Age Range Ages 6+ Operated in English, Italian, Spanish Operator Campania Overland From
- NZ$24,153
Duration 8 days Destinations Civitavecchia, Rome, Amalfi, Capri, Naples, Ravello, Sorrento, Anacapri, Mount Vesuvius, PompeiiSee all destinations Age Range Ages 12+ Operator Emerald Cruises From $24,995
50% Off- NZ$12,437You save $12,558
Amalfi Coast by Luxury Sailing Boat - Walking with the Gods
2 Reviews by TourRadar travelers“The boat was nice and clean. The itinerary was well planned so the trip was really relaxing and enjoyable.”
Alexis, traveled in June
The luxurious 57ft yacht takes you along South Italy's coast, passing Capri's Blue Grotto and the iconic Faraglioni Rocks. The route from Marina di Stabia through Sorrento Coast to Positano includes swimming in Nerano Bay and Li Galli islands. Onboard accommodation, skipper, and hostess service costs approx. $460 per day.
No departure dates availableDuration 3 days Destinations Castellammare di Stabia, Capri, Amalfi, Positano, Sorrento Age Range All Ages Welcome Operated in English, Italian Operator Sail And Experience 
Duration 11 days Destinations Valletta, Syracuse, Giardini Naxos, Lipari, Amalfi, Capri, Sorrento, Gaeta, Porto Ercole, PortoferraioSee all destinations Age Range Ages 12+ Operator Emerald Cruises From $32,757
50% Off- NZ$16,344You save $16,413
Delicious Amalfi Coast - Luxury Sailing Catamaran ALL INCLUSIVE
1 Review by TourRadar travelers“This is a great opportunity to discover the Amalfi coast in great company. He will make you feel like home even on the other side of the world!”
Barney, traveled in September
The luxury catamaran glides through South Italy's coastline, revealing hidden caves near Recommone and secluded bays. The voyage includes stops at Scala Fenicia winery and traditional lemon groves, while professional crew showcases Naples Gulf's highlights.
No departure dates availableDuration 7 days Destinations Castellammare di Stabia, Procida, Ischia, Capri, Positano, Amalfi, Sorrento, Pompeii Age Range All Ages Welcome Operated in English, Italian Operator Sail And Experience 
The Bavaria C57 yacht sails South Italy's pristine waters, showcasing hidden gems like Palmarola's caves and Ponza's Chiaia di Luna. Navigation skills training comes with five island destinations, expert instruction, and half-board dining.
No departure dates availableDuration 7 days Destinations Castellammare di Stabia, Ischia, Ventotene Island, Ponza, Procida Age Range All Ages Welcome Operated in English, Italian Operator Sail And Experience 
The Lagoon 42 takes you through Southern Italy's Aeolian archipelago from Messina. The eight-day voyage includes Vulcano's therapeutic bays, Stromboli's active crater, and Panarea's exclusive harbors, with professional crew, half-board meals, and secluded Mediterranean coves.
No departure dates availableDuration 8 days Destinations Messina, Vulcano, Panarea Island, Stromboli, Salina, Filicudi Island, Lipari Age Range Ages 18+ Operator Med Sailing Holidays 
The Lagoon 42 catamaran takes you through South Italy's Aeolian archipelago. Eight days of sailing instruction includes routes along Stromboli's volcanic coast, Vulcano's thermal waters, and Panarea's hidden coves, complete with hands-on navigation training.
No departure dates availableDuration 8 days Destinations Messina, Vulcano, Panarea Island, Stromboli, Salina, Filicudi Island, Lipari Age Range Ages 18+ Operator Med Sailing Holidays
What our customers ask about Sailing Tours & Trips in South Italy
What are the typical routes and destinations covered on South Italy sailing tours?
South Italian sailing tours focus on two main regions: the Aeolian Islands and the Amalfi Coast. From Milazzo boats head to the Aeolian archipelago where travelers explore volcanic islands such as Stromboli Panarea and Lipari. These stops include visits to local pumice quarries and swimming in clear Mediterranean waters. The Amalfi Coast routes start from Castellammare di Stabia or Civitavecchia taking sailors past Capri's Faraglioni Rocks through Positano's coastal views and into the historic center of Amalfi. A TourRadar traveler noted: "We sailed along the Amalfi coast visited Capri Positano and Sorrento. The itinerary was well planned so the trip was really relaxing and enjoyable."
What kind of boats are typically used for South Italy sailing tours?
The fleet ranges from modern catamarans to classic wooden gulets with space for 8 to 14 guests. Most tours use 48-52ft yachts that feature 4 double-share cabins and 2-3 shared bathrooms. Some operators opt for larger vessels like the Lagoon 42 complete with air conditioning and water makers. "The Bavaria 51 was a delight to sail. Very stable responsive and fast" reported one TourRadar traveler during their stay at Marina di Stabia. The boats balance social spaces with practical sleeping areas to create a genuine sailing experience without sacrificing comfort.
What are the top activities to enjoy during stopovers while sailing South Italy?
Each stop offers distinct experiences throughout South Italy's sailing routes. On the Aeolian Islands visitors can climb Stromboli's active volcano or enjoy dinner with volcanic views at Osservatorio restaurant. Panarea offers swimming in mineral-rich waters near Lisca Bianca and archaeological exploration at Cala Junco's prehistoric village. The Amalfi Coast features Capri's Blue Grotto boat tours hidden swimming spots and coastal hiking. As one TourRadar traveler shared: "The Path of Gods itinerary is splendid." Local wine tastings secluded beach visits and historic town tours round out the experience at each port.
What are the best local dishes to try when sailing South Italy?
Coastal Italian cuisine takes center stage during sailing trips with fresh seafood and regional specialties. The Aeolian Islands serve local favorites like 'pasta con i ricci' at Filippino restaurant in Lipari while onboard chefs prepare just-caught fish. Amalfi Coast highlights include authentic Caprese salad made with Sorrento's 'fior di latte' mozzarella and refreshing granita from Da Alfredo bar in Salina. TourRadar travelers praise the food quality noting tours that include "fantastic local wines dishes of the Sicilian culinary tradition fresh fish cooked with excellence ability by our cooks."
How does dining work on South Italy sailing tours?
The standard arrangement includes half-board meals with breakfast and one main meal (lunch or dinner) provided on the boat. Italian breakfast spreads feature local pastries and coffee while main meals highlight regional seafood and specialties. A TourRadar traveler shared: "Paolo was an extraordinary host. He was easy going and made us feel welcome from the outset. The boat was spacious and comfortable. Organising the kitty and meals went smoothly and we ate like queens." Free meals allow for exploration of local spots such as Bar Zagara in Positano or family-run trattorias in Procida.
What should I pack for a sailing tour in South Italy?
Key items for South Italy sailing include quick-dry swimwear non-marking boat shoes and light breathable clothes. Sun protection is essential: pack strong SPF sunscreen sunglasses and a good hat. Bring a light water-resistant jacket for sea spray and smart casual outfits for evening dining. One TourRadar traveler suggests: "Make sure to pack towel hooks for the heads and remember voltage adapters as power supply can vary from 12V to 220V." For stays at upscale venues like Grand Hotel Vesuvio in Naples smart casual dress is expected for dinner.