Sailing Tours & Trips in South Italy
4.6 stars on(8,985 reviews)- Choose from 20 South Italy tours
- 5,800+ verified reviews from TourRadar travelers
- 24/7 customer support
10 best sailing South Italy tours
Compiled by
MelissaSouth Italy travel expert at TourRadar
- Amalfi Coast Sailing Adventure (8 destinations)
- Amalfi Coast Sailing Adventure (10 destinations)
- Amalfi Coast by Luxury Sailing Boat - Walking with the Gods
- Delicious Amalfi Coast - Luxury Sailing Catamaran ALL INCLUSIVE
- Aeolian Islands Cruise in Gulet 2025
- A week on board a fantastic motor boat in the Gulf of Naples between the Amalfi and Sorrento coasts
- Private Mini-Cruise around Gulf of Naples, 4 Days (Klase 50) (On Request)
- Private Mini-Cruise around Gulf of Naples, 3 Days (Conam 58) (On Request)
- New Gulet Cruise among Aeolian Islands, Sicily
- Yachting Sicily to Elba via the Amalfi Coast
Amalfi Coast Sailing Adventure (8 destinations)
8 Reviews by TourRadar travelers“It's a great (and cheap) way to see a stretch of coast that is super expensive to stay on. All the local produce tastes ridonc'a'donk.”
Kris, traveled in August
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 7 days Destinations Procida, Ischia, Sorrento, Pompeii, Amalfi, Capri, Forio Age Range Ages 15+ Operator Intrepid Travel From
- NZ$3,875+$177 local payments
Duration 8 days Destinations Procida, Ischia, Sorrento, Pompeii, Amalfi, Capri, Forio Age Range Ages 15+ Operator Intrepid Travel From $4,675
20% Off- NZ$3,740+$177 local paymentsYou save $935
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 All Ages Welcome Operated in English, Italian Operator Sail And Experience From
20% Off- NZ$4,725+$591 local payments
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 All Ages Welcome Operated in English, Italian Operator Sail And Experience From
20% Off- NZ$10,336+$984 local payments
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 Ages 6+ Operator Dimensione Sicilia - Dimsi Incoming Operator Srl From
20% Off- NZ$3,544+$807 local payments
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
20% Off- NZ$23,624
No departure dates availableDuration 4 days Destinations Sorrento, Capri, Amalfi, Positano Age Range All Ages Welcome Operator TUI Italia 
Duration 3 days Destinations Sorrento, Capri, Amalfi Age Range All Ages Welcome Operator TUI Italia From $12,675
10% Off- NZ$11,408You save $1,268
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 Ages 18+ Operator Soleto Travel From
10% Off- NZ$3,898
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 $31,951
50% Off- NZ$15,942You save $16,009
What people love about Sailing Tours in South Italy
- Amalfi Coast Sailing Adventure (8 destinations)
This was pretty insane. It's a great (and cheap) way to see a stretch of coast that is super expensive to stay on. The people on the boat were heaps of fun - only 7 others, but all hilarious and willing to pitch in for food prep etc. You have a small 'kitty' where you buy your groceries for the time on the boat - but dont be put off - that's the best part. All the local produce tastes ridonc'a'donk and they didnt mind us buying red wine even though the notes said we couldnt.
Beautiful landscapes, pleasant sailing, nice team, excellent skipper. Two points must be mentioned : 1) The « walking with the gods » itinerary is splendid may be physically difficult for people over 70 and overweight (which is my case). Mountain shoes and walking poles are recommended. 2) Unfortunately counter-wind forced the skipper to use the engine most of the time.
Amalfi Coast by Luxury Sailing Boat - Walking with the Gods
- New Gulet Cruise among Aeolian Islands, Sicily
This was a fun and friendly tour around the island...it could have been a little less windy :-/ Thanos and crew did a greta job!
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.