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Sailing Tours & Trips in South Italy
Sailing Tours & Trips in South Italy

Sailing Tours & Trips in South Italy

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  • Choose from 19 South Italy tours
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  1. Amalfi Coast Sailing AdventureMap of Amalfi Coast Sailing Adventure
    Sailing

    A week-long sailing adventure aboard a 48-52ft yacht takes you through hidden coves between Procida and Ischia. The route passes Castello Aragonese and leads to secluded swimming spots. Traditional fishing villages dot the coastline during this authentic maritime experience.

    Duration 8 days
    DestinationsProcida, Ischia, Sorrento, Pompeii, Amalfi, Capri, Forio
    Age Range Ages 15+
    OperatorIntrepid Travel

    From $3,210

    15% Off
    US$2,728
    +$93 local payments
    You save $482
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  2. Amalfi Coast by Luxury Sailing Boat - Walking with the GodsMap of Amalfi Coast by Luxury Sailing Boat - Walking with the Gods
    Sailing

    The luxurious 57ft yacht takes you along South Italy's coast, passing Capri's Blue Grotto and the iconic Faraglioni Rocks. The route from Marina di Stabia through Sorrento Coast to Positano includes swimming in Nerano Bay and Li Galli islands. Onboard accommodation, skipper, and hostess service costs approx. $460 per day.

    Duration 3 days
    DestinationsCastellammare di Stabia, Capri, Amalfi, Positano, Sorrento
    Age Range All Ages Welcome
    Operated in English, Italian
    OperatorSail And Experience

    From

    15% Off
    US$2,795
    +$349 local payments
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  3. Delicious Amalfi Coast - Luxury Sailing Catamaran ALL INCLUSIVEMap of Delicious Amalfi Coast - Luxury Sailing Catamaran ALL INCLUSIVE
    Sailing

    The luxury catamaran glides through South Italy's coastline, revealing hidden caves near Recommone and secluded bays. The voyage includes stops at Scala Fenicia winery and traditional lemon groves, while professional crew showcases Naples Gulf's highlights.

    Duration 7 days
    DestinationsCastellammare di Stabia, Procida, Ischia, Capri, Positano, Amalfi, Sorrento, Pompeii
    Age Range All Ages Welcome
    Operated in English, Italian
    OperatorSail And Experience

    From

    15% Off
    US$6,113
    +$582 local payments
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  4. Aeolian Islands Cruise in Gulet 2025Map of Aeolian Islands Cruise in Gulet 2025
    Sailing

    A 26-meter traditional gulet awaits in South Italy's volcanic paradise. Professional crew leads visits to Stromboli's active crater, Panarea's ancient ruins, and Filicudi's sea caves, with snorkeling equipment provided for underwater exploration.

    Duration 8 days
    DestinationsMilazzo, Stromboli, Panarea Island, Lipari, Filicudi Island, Salina, Vulcano
    Age Range Ages 6+
    Operated in English, German, Italian, French, Spanish
    OperatorDimensione Sicilia - Dimsi Incoming Operator Srl

    From

    15% Off
    US$2,096
    +$477 local payments
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  5. New Gulet Cruise among Aeolian Islands, SicilyMap of New Gulet Cruise among Aeolian Islands, Sicily
    Sailing

    A traditional gulet carries you through South Italy's volcanic paradise. The route includes Strombolicchio lighthouse, swimming in Lisca Bianca's thermal waters, and hidden caves at Filicudi, while expert crew guides through Aeolian archipelago's best anchorages.

    Duration 8 days
    DestinationsMilazzo, Stromboli, Panarea Island, Lipari, Filicudi Island, Salina, Vulcano
    Age Range Ages 18+
    OperatorSoleto Travel

    From

    15% Off
    US$2,306
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  6. Private Mini-Cruise around Gulf of Naples, 4 Days (Conam 58) (On Request)Map of Private Mini-Cruise around Gulf of Naples, 4 Days (Conam 58) (On Request)
    Sailing
    Duration 4 days
    DestinationsSorrento, Capri, Amalfi, Positano
    Age Range All Ages Welcome
    OperatorTUI Italia

    From $9,357

    10% Off
    US$8,421
    You save $936
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  7. Private Mini-Cruise around Gulf of Naples, 4 Days (Klase 50) (On Request)Map of Private Mini-Cruise around Gulf of Naples, 4 Days (Klase 50) (On Request)
    Sailing
    Duration 4 days
    DestinationsSorrento, Capri, Amalfi, Positano
    Age Range All Ages Welcome
    OperatorTUI Italia

    From $14,517

    10% Off
    US$13,065
    You save $1,452
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  8. Italian Treasures: Amalfi Coast, Sicily and MaltaMap of Italian Treasures: Amalfi Coast, Sicily and Malta
    Sailing

    The Scenic Eclipse II luxury vessel takes you from Civitavecchia along South Italy's coast. Ports include Capri's marina, Amalfi's historic harbor, and UNESCO-listed Aeolian Islands, featuring butler service and gourmet dining venues.

    Duration 8 days
    DestinationsCivitavecchia, Capri, Amalfi, Lipari, Giardini Naxos, Pozzallo, Mgarr, Valletta
    Age Range Ages 12+
    OperatorScenic Luxury Cruises & Tours

    From $18,990

    50% Off
    US$9,490
    You save $9,500
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  9. Yachting Sicily to Elba via the Amalfi CoastMap of Yachting Sicily to Elba via the Amalfi Coast
    Sailing
    Duration 11 days
    DestinationsValletta, Syracuse, Giardini Naxos, Lipari, Amalfi, Capri, Sorrento, Gaeta, Porto Ercole, PortoferraioSee all destinations
    Age Range Ages 12+
    OperatorEmerald Cruises

    From $18,990

    50% Off
    US$9,475
    You save $9,515
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  10. Following Ulysses - Luxury Sailing Boat ALL INCLUSIVEMap of Following Ulysses - Luxury Sailing Boat ALL INCLUSIVE
    Sailing

    The Bavaria C57 yacht sails South Italy's pristine waters, showcasing hidden gems like Palmarola's caves and Ponza's Chiaia di Luna. Navigation skills training comes with five island destinations, expert instruction, and half-board dining.

    Duration 7 days
    DestinationsCastellammare di Stabia, Ischia, Ventotene Island, Ponza, Procida
    Age Range All Ages Welcome
    Operated in English, Italian
    OperatorSail And Experience

    From

    50% Off
    US$5,240
    +$582 local payments
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