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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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 - 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
10 best Sailing Italy tour packages
Compiled by
MelissaItaly travel expert at TourRadar
- Amalfi Coast Sailing Adventure
- Med Sailing in Sicily
- Sailing the Aeolian Islands Dream - 8 days of gulet escape
- Yoga Sailing in Sardinia and Corsica
- 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
- Med 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
- US$3,080+$105 local payments
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
- US$2,446
Duration 8 days Destinations Stromboli, Panarea Island, Salina, Lipari, Vulcano Age Range Ages 10+ Operator Towns of Italy From
- US$5,852
The Lagoon 42 catamaran combines sailing and yoga along Italy's stunning coastline. Practice poses overlooking Olbia's harbor and Tavolara's dramatic cliffs. The journey includes Costa Smeralda's pristine waters and Caprera Island's sunrise sessions, with freshly prepared Mediterranean meals.
Duration 8 days Destinations Olbia, Cannigione, La Maddalena, Bonifacio, Caprera Island Age Range Ages 18+ Operator Med Sailing Holidays From
- US$2,680
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
- US$2,294
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
- US$2,195
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
- US$1,463
The Emerald Sakara takes you along Italy's Mediterranean coast from Civitavecchia to Porto Cervo, stopping at UNESCO-listed sites like Pompeii's ancient Roman streets and the Giants' Tomb on Sardinia. Bonifacio's medieval citadel sits on Corsica's limestone cliffs and you can see the historic Madonetta lighthouse during the sailing. Sperlonga's white houses overlook azure waters and make for a nice stroll. All meals, port taxes, and airport transfers come with the package, plus optional excursions to Anacapri's Villa Munthe and La Maddalena Archipelago.
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 $15,890
61% Off- US$6,240You save $9,650
The Emerald Azzurra glides through Italy's most coveted coastlines, from Santa Margherita's elegant promenade to Porto Venere's UNESCO heritage. Savor Portofino's harbor-side dining, Livorno's seafood specialties, and Marina di Carrara's marble cliffs. Luxury yacht offers 72 crew members serving maximum 100 passengers.
Duration 8 days Destinations France, Monaco, Italy Age Range Ages 12+ Operator Emerald Cruises From $16,240
60% Off- US$6,518You save $9,722
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
60% Off- US$2,680
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."