Sailing Tours & Trips in South Italy
4.5 stars on(7,892 reviews)- Choose from 14 South Italy tours
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10 best sailing South Italy tours
Compiled by
MelissaSouth Italy travel expert at TourRadar
- Delicious Amalfi Coast - Luxury Sailing Catamaran ALL INCLUSIVE
- Amalfi Coast by Luxury Sailing Boat - Walking with the Gods
- Amalfi Coast Sailing Adventure
- Med Sailing in Sicily
- Aeolian Islands Cruise in Gulet 2025
- New Gulet Cruise among Aeolian Islands, Sicily
- Italian Treasures: Amalfi Coast, Sicily and Malta
- Following Ulysses - Luxury Sailing Boat ALL INCLUSIVE
- Capri and Amalfi Coast by Catamaran
- A week on board a fantastic motor boat in the Gulf of Naples between the Amalfi and Sorrento coasts
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.
Duration 7 days Destinations Castellammare di Stabia, Procida, Ischia, Capri, Positano, Amalfi, Sorrento, Pompeii Age Range up to 70 year olds Operated in English, Italian Operator Sail And Experience From
- US$1,849+$543 local payments
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.
Duration 3 days Destinations Castellammare di Stabia, Capri, Amalfi, Positano, Sorrento Age Range up to 70 year olds Operated in English, Italian Operator Sail And Experience From
- US$1,305+$326 local payments
A week-long sailing adventure aboard a 48-52ft yacht takes you through hidden coves between Procida and Ischia. The route passes Castello Aragonese and leads to secluded swimming spots. Traditional fishing villages dot the coastline during this authentic maritime experience.
Duration 8 days Destinations Procida, Ischia, Sorrento, Pompeii, Amalfi, Capri, Forio Age Range 15 to 99 year olds Operator Intrepid Travel From $3,145
30% Off- US$2,201+$87 local paymentsYou save $944
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.
Duration 8 days Destinations Messina, Vulcano, Panarea Island, Stromboli, Salina, Filicudi Island, Lipari Age Range 18 to 80 year olds Operator Med Sailing Holidays From
30% Off- US$2,164
Aeolian Islands Cruise in Gulet 2025
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 6 to 90 year olds Operated in English, German, Italian, French, Spanish Operator Dimensione Sicilia - Dimsi Incoming Operator Srl From
30% Off- US$1,957+$445 local payments
New Gulet Cruise among Aeolian Islands, Sicily
2 Reviews by TourRadar travelers“This was a fun and friendly tour around the island.”
Fred, traveled in June
A traditional gulet carries you through South Italy's volcanic paradise. The route includes Strombolicchio lighthouse, swimming in Lisca Bianca's thermal waters, and hidden caves at Filicudi, while expert crew guides through Aeolian archipelago's best anchorages.
Duration 8 days Destinations Milazzo, Stromboli, Panarea Island, Lipari, Filicudi Island, Salina, Vulcano Age Range up to 90 year olds Operator Soleto Travel From
30% Off- US$2,153
The Scenic Eclipse II luxury vessel takes you from Civitavecchia along South Italy's coast. Ports include Capri's marina, Amalfi's historic harbor, and UNESCO-listed Aeolian Islands, featuring butler service and gourmet dining venues.
Duration 8 days Destinations Civitavecchia, Capri, Amalfi, Lipari, Giardini Naxos, Pozzallo, Mgarr, Valletta Age Range up to 99 year olds Operator Scenic Luxury Cruises & Tours From $22,490
50% Off- US$11,240You save $11,250
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.
Duration 7 days Destinations Castellammare di Stabia, Ischia, Ventotene Island, Ponza, Procida Age Range up to 70 year olds Operated in English, Italian Operator Sail And Experience From
50% Off- US$2,392+$543 local payments
Luxury catamaran cruising reveals South Italy's azure waters with en-suite comfort. The route encompasses Capri's Blue Grotto, Faraglioni Rocks, and Li Galli islands. From Marina di Stabia, visitors enjoy Sorrento's historic center and local fior di latte mozzarella during half-board meals.
Duration 3 days Destinations Castellammare di Stabia, Sorrento, Capri, Amalfi, Positano Age Range up to 70 year olds Operated in English, Italian Operator Sail And Experience From
50% Off- US$1,251+$271 local payments
Duration 7 days Destinations Forio, Procida, Capri, Sorrento, Nerano, Positano, Amalfi, Vietri sul Mare, Ischia Age Range 6 to 120 year olds Operated in Only: Italian Operator Campania Overland From
50% Off- US$13,593
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.