Sailing Tours & Trips in South Italy
4.5 stars on(7,472 reviews)- Choose from 13 South Italy tours
- 31 verified reviews from TourRadar travelers
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10 best sailing South Italy tours
Compiled by
MelissaSouth Italy travel expert at TourRadar
- Amalfi Coast by Luxury Sailing Boat - Walking with the Gods
- Delicious Amalfi Coast - Luxury Sailing Catamaran ALL INCLUSIVE
- Med Sailing in Sicily
- New Gulet Cruise among Aeolian Islands, Sicily
- Italian Treasures: Amalfi Coast, Sicily and Malta
- Following Ulysses - Luxury Sailing Boat ALL INCLUSIVE
- Capri and Amalfi Coast by Catamaran
- Aeolian Islands Cruise in Gulet 2025
- Pride Sailing in Sicily
- Segeltörn zum Vulkan Stromboli in Sizilien
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 2019
- Set sail from Marina di Stabia to Capri
- Explore the Blue Grotto in small boats
- Hike the stunning trails from Bomerano to Nocelle
Duration 3 days Destinations Castellammare di Stabia, Capri, Amalfi, Positano, Sorrento Age Range up to 70 year olds Operated in English, Italian Operator Sail And Experience From
- US$1,236+$309 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 2019
- Sail through Napoli Gulf with Italian Aperitif
- Relax in thermal pools at Sorgeto Bay, Ischia
- Explore Capri's wineries and iconic Piazzetta
Duration 7 days Destinations Castellammare di Stabia, Procida, Ischia, Capri, Positano, Amalfi, Sorrento, Pompeii Age Range up to 70 year olds Operated in English, Italian Operator Sail And Experience From
- US$1,751+$515 local payments
- Relax in Vulcano's therapeutic mud baths
- Explore Panarea's boutique shops and coves
- Watch lava flows at sunrise in Stromboli
Duration 8 days Destinations Messina, Vulcano, Panarea Island, Stromboli, Salina, Filicudi Island, Lipari Age Range 18 to 80 year olds Operated in English Operator Med Sailing Holidays From
- US$2,050
- Swim in Sant’Antonio Bay under the stars
- Hike Stromboli's active volcano crater
- Explore the prehistoric village at Cala Junco
Duration 8 days Destinations Milazzo, Stromboli, Panarea Island, Lipari, Filicudi Island, Salina, Vulcano Age Range up to 90 year olds Operated in English Operator Soleto Travel From
- US$2,040
- Explore ancient Rome from Civitavecchia port
- Discover Capri's charm and taste local delicacies
- Stroll through Amalfi and visit historic Ravello
Duration 8 days Destinations Civitavecchia, Capri, Amalfi, Lipari, Giardini Naxos, Pozzallo, Mgarr, Valletta Age Range up to 99 year olds Operated in English Operator Scenic Luxury Cruises & Tours From $22,140
52% Off- US$10,715You save $11,425
- Set sail from Marina di Stabia to Ischia
- Explore bays and vibrant nightlife in Ponza
- Enjoy a dinghy hike at Palmarola's Faraglioni
Duration 7 days Destinations Castellammare di Stabia, Ischia, Ventotene Island, Ponza, Procida Age Range up to 70 year olds Operated in English, Italian Operator Sail And Experience From
52% Off- US$2,266+$515 local payments
- Set sail along the stunning Sorrento Coast
- Explore historic Sorrento and taste local mozzarella
- Anchor at Capri for views of the Faraglioni Rocks
Duration 3 days Destinations Castellammare di Stabia, Sorrento, Capri, Amalfi, Positano Age Range up to 70 year olds Operated in English, Italian Operator Sail And Experience From
52% Off- US$1,185+$257 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 2023
- Swim in Sant’Antonio Bay under starlight
- Scale Stromboli's active volcano
- Explore Panarea's prehistoric village ruins
Duration 8 days Destinations Milazzo, Stromboli, Panarea Island, Lipari, Filicudi Island, Salina, Vulcano Age Range 6 to 90 year olds Operated in English Operator Dimensione Sicilia - Dimsi Incoming Operator Srl From
52% Off- US$1,854+$422 local payments
- Relax in Vulcano's therapeutic mud baths
- Shop and dine in charming Panarea
- Watch lava flows at sunrise in Stromboli
No departure dates availableDuration 8 days Destinations Messina, Vulcano, Panarea Island, Stromboli, Salina, Filicudi Island, Lipari Age Range 18 to 80 year olds Operated in English Operator Med Sailing Holidays 
- Set sail from Sicily's marina
- Anchor at Vulcano's volcanic bay
- Watch Stromboli's glowing lava at night
No departure dates availableDuration 8 days Destinations Palermo, Vulcano, Panarea Island, Stromboli, Salina Age Range up to 105 year olds Operated in Only: German Operator Sailorama Segelreisen
