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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- Choose from 30 Italy tours
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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 - B
Barney • traveled in October
This is a great opportunity to discover the Amalfi coast in great company. Sergio is a genuine nice guy and is very customer focused. He will make you feel like home even on the other side of the world !
Delicious Amalfi Coast - Luxury Sailing Catamaran ALL INCLUSIVE - J
Jacqueline • traveled in July
Food, itinerary, crew were excellent. Had a lovely time.
Aeolian Islands Cruise in Gulet 2026
10 best Sailing Italy tour packages
Compiled by
MelissaItaly travel expert at TourRadar
- Sailing the Amalfi Coast: Capri, Positano & Coastal Bliss
- Delicious Amalfi Coast - Luxury Sailing Catamaran ALL INCLUSIVE
- Amalfi Coast by Luxury Sailing Boat - Walking with the Gods
- Amalfi Coast Sailing Adventure
- Pride Sailing in Sicily
- Med Sailing in Sardinia and Corsica
- New Gulet Cruise among Aeolian Islands, Sicily
- Aeolian Islands Cruise in Gulet 2026
- Tuscany to the Amalfi Coast: Italy by Land & Sea
- Enchanting Italian Coastlines
Duration 7 days Destinations Naples, Procida, Ischia, Capri, Positano, Amalfi, Ravello, Sorrento Age Range Ages 12+ Operator G Adventures From $2,599
50% Off- US$1,300You save $1,300
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
A 43ft luxury catamaran takes you through Italy's finest waters, visiting eight destinations from Procida to Pompeii. Secluded bays like San Pancrazio and hidden caves near Recommone await. Professional crew offers sailing lessons while guiding through scenic coastlines.
Duration 7 days Destinations Castellammare di Stabia, Procida, Ischia, Forio, Capri, Positano, Amalfi, Sorrento, Pompeii Age Range All Ages Welcome Operated in English, Italian Operator Sail And Experience From
50% Off- US$6,962+$348 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
A 57ft yacht carries you along Italian waters, from Marina di Stabia to Capri's Blue Grotto. Navigate past Faraglioni Rocks and Li Galli islands while learning sailing basics. Professional skipper guides this three-day journey along Amalfi Coast's dramatic cliffs.
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
50% Off- US$3,133+$290 local payments
Amalfi Coast Sailing Adventure
“Even in the tight quarters, we were all reasonably comfortable. We had dinner as a group each night at excellent restaurants.”
Barbara, traveled in May
Duration 7 days Destinations Naples, Procida, Ischia, Sorrento, Pompeii, Mount Vesuvius, Amalfi, Capri, Anacapri Age Range Ages 15+ Operator Intrepid Travel From $2,915
40% Off- US$1,749+$104 local paymentsYou save $1,166
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
40% Off- US$2,657
The Lagoon 42 catamaran guides you through Italy's crystal waters between Olbia and Costa Smeralda. Learn anchoring at Tavolara's marine reserve, wind reading near Porto Pollo's coast, and mooring techniques in Cannigione's picturesque harbor under expert guidance.
Duration 8 days Destinations Olbia, Cannigione, La Maddalena, Bonifacio, Caprera Island Age Range Ages 18+ Operator Med Sailing Holidays From
40% Off- US$2,657
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 $2,274
18% Off- US$1,865You save $409
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."