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.
Excellent
- Choose from 29 Italy tours
- 8 verified reviews from TourRadar travelers
- 24/7 customer support
- J
Jacqueline • traveled in July
Food, itinerary, crew were excellent. Had a lovely time.
Aeolian Islands Cruise in Gulet 2026 - Z
Ziyuan • traveled in June
We had a great 5-day sailing tour with Sail and experience. The boat was nice and clean. Skipper Anzo was cool and friendly. Organizer Claudia was also kind and helpful. They helped us to arrange transportation between Napoli and the Marina. We sailed along the Amalfi coast, visited Capri, Positano, and Sorrento. The itinerary was well planned so the trip was really relaxing and enjoyable. We were neither rushing to a place nor spending too much time on one spot. The hike on the Path of Gods arranged on the third day was nice. It was an easy hike. Unfortunately it was a foggy day, otherwise the coastline view would be more stunning. Personally will definitely come back to hike on a sunny day in the future. Wish it was a 6-day sail instead of 5-day so we would be able to visit Amalfi and Ravello. Overall great tour and highly recommended. :)
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
- Yoga Sailing in Sardinia and Corsica
- Aeolian Islands Cruise in Gulet 2026
- Enchanting Italian Coastlines
- Hidden Gems of Italy Valletta → Venice (2026)
- French & Italian Rivieras with Corsica 2026 - 8 Days (from Cannes to Civitavecchia)
- Med Sailing in Sardinia and Corsica
- Yachting Sicily to Elba via the Amalfi Coast
- Italy's Islands, Corsica to Monaco
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
- NZ$4,560+$178 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
- NZ$4,145
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
- NZ$4,542
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
- NZ$3,719
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 $26,957
61% Off- NZ$10,586You save $16,371
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 $27,551
60% Off- NZ$11,058You save $16,493
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- NZ$4,542
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 $32,216
56% Off- NZ$14,293You save $17,923
Duration 11 days Destinations Italy, France, Monaco Age Range Ages 12+ Operator Emerald Cruises From $31,368
50% Off- NZ$15,625You save $15,743
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."