Sailing Tours & Trips in Italy
Picture this: you're sailing past Procida's colorful houses, soaking in Ischia's hot springs, and wandering through ancient Pompeii before it gets too crowded. Cruise around Capri's grottoes, stroll Amalfi's winding streets, relax in Positano, and maybe even catch Stromboli erupting at night. Honestly, the Mediterranean doesn't get much better than this. Italy's waiting.
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Jacqueline • traveled in July
Food, itinerary, crew were excellent. Had a lovely time.
Aeolian Islands Cruise in Gulet 2026 - K
KALMANS • traveled in October
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
10 best Sailing Italy tour packages
Compiled by
MelissaItaly travel expert at TourRadar
- Amalfi Coast Sailing Adventure
- Pride Sailing in Sicily
- Sailing the Aeolian Islands Dream - 8 days of gulet escape
- Med Sailing in Sicily
- New Gulet Cruise among Aeolian Islands, Sicily
- 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
- French & Italian Rivieras with Corsica 2026 - 8 Days (from Cannes to Civitavecchia)
- Yoga Sailing in Sardinia and Corsica
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 $3,080
16% Off- US$2,594+$107 local paymentsYou save $486
A fully-crewed Lagoon 42 catamaran sails through Italy's Aeolian Islands. The route from Messina includes hidden coves around Vulcano, Stromboli's volcanic displays, and Salina's wine country. Eight days of Mediterranean sailing features Panarea's exclusive ports and Filicudi's unspoiled beaches with professional navigation and gourmet half-board meals.
Duration 8 days Destinations Messina, Vulcano, Panarea Island, Stromboli, Salina, Filicudi Island, Lipari Age Range Ages 18+ Operator Med Sailing Holidays From
16% Off- US$2,605
Duration 8 days Destinations Stromboli, Panarea Island, Salina, Lipari, Vulcano Age Range Ages 10+ Operator Towns of Italy From
16% Off- US$5,948
A Lagoon 42 catamaran departs Messina, taking you through Italian waters to seven Aeolian Islands. Master sailing techniques while visiting Vulcano's black beaches, Panarea's hidden coves, and Stromboli's active volcano. Professional skipper shares navigation skills during this 8-day Mediterranean adventure.
Duration 8 days Destinations Messina, Vulcano, Panarea Island, Stromboli, Salina, Filicudi Island, Lipari Age Range Ages 18+ Operator Med Sailing Holidays From
16% Off- US$2,486
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 takes you through Italy's Tyrrhenian Sea to the Aeolian archipelago's volcanic islands. Highlights include Strombolicchio lighthouse, Cala Junco's prehistoric site, and swimming in Vulcano's Pool of Venus. Expert crew guides you to hidden coves.
Duration 8 days Destinations Milazzo, Stromboli, Panarea Island, Lipari, Filicudi Island, Salina, Vulcano Age Range Ages 18+ Operator Soleto Travel From
16% Off- US$2,331
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 luxurious 26-meter gulet takes you through Italy's Aeolian archipelago. Seven volcanic islands await, from Stromboli to Filicudi, with swimming at Lipari's pumice beaches and snorkeling in Panarea's crystal waters. Expert crew handles navigation while you relax.
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
16% Off- US$2,230
Duration 7 days Destinations Forio, Procida, Capri, Sorrento, Nerano, Positano, Amalfi, Vietri sul Mare, Ischia Age Range Ages 6+ Operated in English, Italian Operator Campania Overland From
16% Off- US$1,487
What our customers ask about Sailing Tours & Trips in Italy
What are the best routes and destinations covered on Italy sailing tours?
Italy sailing tours take travelers through three main regions: the Aeolian Islands Amalfi Coast and Sardinia. From Castellammare di Stabia boats navigate to well-known destinations like Capri Positano and the small island of Procida. The Aeolian Islands route takes sailors past active volcanoes including Stromboli Vulcano and Panarea. Sardinia's routes focus on the Costa Smeralda with stops in Tavolara and Bonifacio. As one TourRadar traveler noted: "Beautiful landscapes, pleasant sailing, nice team, excellent skipper. The landscapes along the Amalfi coast were absolutely stunning."
What is the best time of year to sail in Italy?
The best sailing months run from May to September with each region offering different advantages. The Amalfi Coast offers clear skies and calm waters from June to September with temperatures between 75-85°F. Sardinia works best in July and August. May and September see fewer tourists and temperatures around 70°F making these months good alternatives. According to TourRadar travelers: "We had some rough weather during our trip, but our skipper Noon chose spots to anchor or harbors that were safe and out of the bad weather, making the experience still enjoyable."
What type of boats are typically used for Italian sailing tours?
Tours use various boats ranging from modern catamarans to traditional vessels. In Sardinia the Lagoon 42 catamaran is common featuring 4 en-suite cabins and open living spaces. Amalfi Coast operators prefer 48-52ft yachts that fit 8 guests in 4 double-share cabins. Companies like Soleto Travel use traditional wooden gulets with 7 cabins for Aeolian Islands trips. As one TourRadar traveler noted: "The boat was in great condition. The Bavaria 51 was a delight to sail. Very stable, responsive and fast."
What kind of meals are typically included on Italian sailing tours?
Most tours provide breakfast and lunch on board while dinner happens at local restaurants. The food focuses on local ingredients with plenty of seafood pasta and regional dishes. Aeolian Islands tours often include half-board arrangements where an on-board cook prepares breakfast and lunch. A TourRadar traveler praised: "Paolo cooked food for us and that was some of the best Italian food I have ever had. At harbors he took us to fantastic restaurants and great little bars."
What are the best activities to enjoy during stopovers?
Each stop offers unique experiences from exploring Pompeii to swimming in secluded coves. Visitors can see the Blue Grotto in Capri walk the Path of Gods on the Amalfi Coast visit local wineries or go snorkeling in the Maddalena Archipelago. As one TourRadar traveler noted: "We had the perfect balance of cultural visits, swimming in beautiful bays, and exploring charming coastal towns."
What's the typical group size on Italian sailing tours?
These tours keep groups small with 8-14 passengers per boat. Sardinia's luxury catamarans usually take 8-10 guests while traditional gulets in the Aeolian Islands can accommodate up to 14 people. A TourRadar traveler shared: "With only 8 people on board, we really got to know each other and the skipper could give us personalized attention and recommendations."