All Italy Sailing Holidays
Italy’s coastline is made for exploring by boat, from the dramatic cliffs of the Amalfi Coast to the volcanic Aeolian Islands and Sardinia’s turquoise waters. Step ashore to wander cobbled streets, taste local food, or hike volcanic landscapes. With warm seas, steady winds, and stunning scenery, sailing here is unforgettable.
Find out more about sailing holidays in Italy
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We have found 40 voyages with berths available.
Exclusive Private Catamaran Charter: Sardinia & Corsica
Enjoy a private catamaran charter and explore the coastline of Sardinia, the La Maddalena islands and historic Bonifacio on Corsica.
Date: 4 Jul 2026
Duration: 8 days
Vessel: Agave
Where: Sardinia, Italy
Board: Half Board
Group Size: 8
Activity: Level 1
i
Was £2,950.00€3,350.00Now £2,655.00€3,015.00
Berths available
Exclusive Private Catamaran Charter: Sardinia & Corsica
Enjoy a private catamaran charter and explore the coastline of Sardinia, the La Maddalena islands and historic Bonifacio on Corsica.
Date: 11 Jul 2026
Duration: 8 days
Vessel: Agave
Where: Sardinia, Italy
Board: Half Board
Group Size: 8
Activity: Level 1
i
£2,950.00€3,350.00
Berths available
Exclusive Private Catamaran Charter: Sardinia & Corsica
Enjoy a private catamaran charter and explore the coastline of Sardinia, the La Maddalena islands and historic Bonifacio on Corsica.
Date: 18 Jul 2026
Duration: 8 days
Vessel: Agave
Where: Sardinia, Italy
Board: Half Board
Group Size: 8
Activity: Level 1
i
£2,950.00€3,350.00
Berths available
Exclusive Private Catamaran Charter: Sardinia & Corsica
Enjoy a private catamaran charter and explore the coastline of Sardinia, the La Maddalena islands and historic Bonifacio on Corsica.
Date: 1 Aug 2026
Duration: 8 days
Vessel: Agave
Where: Sardinia, Italy
Board: Half Board
Group Size: 8
Activity: Level 1
i
£2,950.00€3,350.00
Berths available
Luxury Yacht Sailing in Southern Italy from Sorrento
Sail the Gulf of Naples with a cruise on yacht Chronos as she explores the islands of Ischia and Procida.
Date: 1 Aug 2026
Duration: 8 days
Vessel: Chronos
Where: Gulf of Naples, Italy
Board: Full Board
Group Size: 26
Activity: Level 1
i
£3,570.00€4,200.00
Berths available
Luxury Sailing & Island Hopping in Italy: Capri
Explore the Amalfi coast and Italian islands from Naples with luxury sailing on yacht Chronos.
Date: 8 Aug 2026
Duration: 6 days
Vessel: Chronos
Where: Gulf of Naples, Italy
Board: Full Board
Group Size: 26
Activity: Level 1
i
£2,215.00€2,480.00
Berths available
Exclusive Private Catamaran Charter: Sardinia & Corsica
Enjoy a private catamaran charter and explore the coastline of Sardinia, the La Maddalena islands and historic Bonifacio on Corsica.
Date: 15 Aug 2026
Duration: 8 days
Vessel: Agave
Where: Sardinia, Italy
Board: Half Board
Group Size: 8
Activity: Level 1
i
Was £2,950.00€3,350.00Now £2,655.00€3,015.00
Berths available
REDUCED SOLO OCCUPANCY
Luxury Sailing & Island Hopping in Southern Italy
Enjoy Mediterranean sailing from the Italian harbour of Salerno as you island hop to Sardinia under sail with Chronos.
Date: 15 Aug 2026
Duration: 8 days
Vessel: Chronos
Where: Italy
Board: Full Board
Group Size: 26
Activity: Level 1
i
£3,400.00€3,900.00
Berths available
Exclusive Private Catamaran Charter: Sardinia & Corsica
Enjoy a private catamaran charter and explore the coastline of Sardinia, the La Maddalena islands and historic Bonifacio on Corsica.
Date: 22 Aug 2026
Duration: 8 days
Vessel: Agave
Where: Sardinia, Italy
Board: Half Board
Group Size: 8
Activity: Level 1
i
£2,950.00€3,350.00
Berths available
Mediterranean Island Escape: Luxury Sailing in Sardinia
Explore the dramatic Italian coast with modern classic yacht Chronos as she sails to explore Sardinia, La Maddalena and Bonifacio.
Date: 22 Aug 2026
Duration: 8 days
Vessel: Chronos
Where: Sardinia, Italy
Board: Full Board
Group Size: 26
Activity: Level 1
i
£3,570.00€4,200.00
Berths available
Exclusive Private Catamaran Charter: Sardinia & Corsica
Enjoy a private catamaran charter and explore the coastline of Sardinia, the La Maddalena islands and historic Bonifacio on Corsica.
Date: 29 Aug 2026
Duration: 7 days
Vessel: Agave
Where: Sardinia, Italy
Board: Half Board
Group Size: 8
Activity: Level 1
i
£2,950.00€3,350.00
Berths available
Luxury Sailing Holiday in Sardinia & Corsica
Indulge in a sailing holiday on board luxury catamaran Agave as she explores the islands of Sardinia and Corsica.
Date: 5 Sep 2026
Duration: 8 days
Vessel: Agave
Where: Sardinia, Italy
Board: Half Board
Group Size: 8
Activity: Level 1
i
£2,950.00€3,350.00
Berths available
Historic Tall Ship Sailing in Italy’s Aeolian Islands
Sail the wonders of the Aeolian islands from Italy with classic wooden windjammer Florette. Discover the active volcano of Stromboli and explore ashore on the islands of Lipari & Salina.
Date: 5 Sep 2026
Duration: 8 days
Vessel: Florette
Where: Vibo Valentia, Italy
Board: Half Board
Group Size: 22
Activity: Level 1
i
£1,250.00€1,380.00
Limited berths
Historic Tall Ship Sailing in Italy’s Aeolian Islands
Sail the wonders of the Aeolian islands from Italy with classic wooden windjammer Florette. Discover the active volcano of Stromboli and explore ashore on the islands of Lipari & Salina.
Date: 12 Sep 2026
Duration: 8 days
Vessel: Florette
Where: Vibo Valentia, Italy
Board: Half Board
Group Size: 22
Activity: Level 1
i
£1,250.00€1,380.00
Berths available
Guided Hiking & Sailing in the Aeolian Islands
Enjoy traditional tall ship sailing and guided hiking as you explore the wonders of the Aeolian Islands in Italy.
Date: 19 Sep 2026
Duration: 8 days
Vessel: Florette
Where: Vibo Valentia, Italy
Board: Half Board
Group Size: 22
Activity: Level 1
i
£1,595.00€1,780.00
Berths available
REDUCED SOLO OCCUPANCY
Luxury Yacht Sailing to Cote d’Azur from Sardinia
Explore the dramatic Italian coast with luxury yacht Chronos as she sails to explore Sardinia, Corsica, and Sainte Maxime.
Date: 19 Sep 2026
Duration: 8 days
Vessel: Chronos
Where: Sardinia, Italy / Côte d’Azur
Board: Full Board
Group Size: 26
Activity: Level 1
i
£3,400.00€3,900.00
Berths available
Exclusive Private Catamaran Charter: Sardinia & Corsica
Enjoy a private catamaran charter and explore the coastline of Sardinia, the La Maddalena islands and historic Bonifacio on Corsica.
Date: 26 Sep 2026
Duration: 8 days
Vessel: Agave
Where: Sardinia, Italy
Board: Half Board
Group Size: 8
Activity: Level 1
i
£2,950.00€3,350.00
Berths available
Luxury Holiday Sailing in Venice
Sail the Italian coast from Venice with luxury yacht Kairos as you explore Grado, Trieste and Miramare Castle along the way.
Date: 17 Oct 2026
Duration: 8 days
Vessel: Kairós
Where: Venice, Italy
Board: Full Board
Group Size: 16
Activity: Level 1
i
£2,730.00€3,200.00
Berths available
Discover Italy’s Aegadian Islands on a Luxury Sailing Holiday
Discover the Mediterranean islands off the coast of Sicily with the luxury classic yacht Rhea.
Date: 22 May 2027
Duration: 8 days
Vessel: Rhea
Where: Malta/Italy
Board: Full Board
Group Size: 26
Activity: Level 1
i
£3,100.00€3,500.00
Berths available
Sailing from Malta to Sicily
Join elegant yacht Chronos on a Mediterranean voyage sailing from Malta to Sicily.
Date: 5 Jun 2027
Duration: 8 days
Vessel: Chronos
Where: Malta / Sicily
Board: Full Board
Group Size: 26
Activity: Level 1
i
£3,135.00€3,500.00
Berths available
Luxury Italian Island Hopping: Aeolian Islands
Explore the magic of the Sicilian Coast and the volcanic Aeolian Islands under sail and in the luxury and comfort of Rhea.
Date: 5 Jun 2027
Duration: 8 days
Vessel: Rhea
Where: Sicily, Italy
Board: Full Board
Group Size: 26
Activity: Level 1
i
£3,360.00€3,800.00
Berths available
Aeolian Island Explorer Onboard a Luxury Yacht
Sail with luxury yacht Chronos from the island of Sicily to the UNESCO World Heritage Aeolian Islands.
Date: 12 Jun 2027
Duration: 11 days
Vessel: Chronos
Where: Sicily, Italy
Board: Full Board
Group Size: 26
Activity: Level 1
i
£4,630.00€5,200.00
Berths available
Luxury Sailing Cruise around Italy’s Southern Islands
Discover the magic of the Sicilian Coast from Palermo to Syracuse exploring the Aeolian Islands under sail with luxury yacht Rhea.
Date: 12 Jun 2027
Duration: 8 days
Vessel: Rhea
Where: Sicily, Italy
Board: Full Board
Group Size: 26
Activity: Level 1
i
£3,360.00€3,800.00
Berths available
Mediterranean Luxury Sailing from Sicily to Corfu
Discover the Sicilian Coast sailing from Sicily to Corfu and the magnificent volcanic Aeolian Islands under sail and in the luxury and comfort of Rhea.
Date: 19 Jun 2027
Duration: 7 days
Vessel: Rhea
Where: Italy/Corfu
Board: Full Board
Group Size: 26
Activity: Level 2
i
£2,750.00€3,100.00
Berths available
Aeolian Island Explorer Onboard a Luxury Yacht
Sail with luxury yacht Chronos from the island of Sicily to the UNESCO World Heritage Aeolian Islands.
Date: 22 Jun 2027
Duration: 11 days
Vessel: Chronos
Where: Sicily, Italy
Board: Full Board
Group Size: 26
Activity: Level 1
i
£4,630.00€5,200.00
Berths available
Aeolian Island Explorer Onboard a Luxury Yacht
Sail with luxury yacht Chronos from the island of Sicily to the UNESCO World Heritage Aeolian Islands.
Date: 2 Jul 2027
Duration: 9 days
Vessel: Chronos
Where: Sicily, Italy
Board: Full Board
Group Size: 26
Activity: Level 1
i
£3,900.00€4,450.00
Berths available
Sailing Holiday in Southern Italy
Sail with yacht Chronos to explore the southern coast of Italy from Sicily to the Aeolian Islands and on to the town of Salerno.
Date: 10 Jul 2027
Duration: 8 days
Vessel: Chronos
Where: Sicily / Italy
Board: Full Board
Group Size: 26
Activity: Level 1
i
£3,485.00€3,900.00
Berths available
Sailing holiday along the Amalfi Coast
Join classic yacht Chronos on a sailing holiday along the Amalfi Coast in Italy.
Date: 17 Jul 2027
Duration: 8 days
Vessel: Chronos
Where: Italy
Board: Full Board
Group Size: 26
Activity: Level 1
i
£3,835.00€4,300.00
Berths available
Sailing holiday along the Amalfi Coast
Join classic yacht Chronos on a sailing holiday along the Amalfi Coast in Italy.
Date: 31 Jul 2027
Duration: 8 days
Vessel: Chronos
Where: Italy
Board: Full Board
Group Size: 26
Activity: Level 1
i
£4,010.00€4,500.00
Berths available
Sailing holiday along the Amalfi Coast
Join classic yacht Chronos on a sailing holiday along the Amalfi Coast in Italy.
Date: 7 Aug 2027
Duration: 8 days
Vessel: Chronos
Where: Italy
Board: Full Board
Group Size: 26
Activity: Level 1
i
£4,010.00€4,500.00
Berths available
Short Amalfi Coast Luxury Sailing Holiday
Explore the Amalfi coast and Italian islands under sail from the Bay of Naples with classic yacht Chronos.
Date: 14 Aug 2027
Duration: 5 days
Vessel: Chronos
Where: Italy
Board: Full Board
Group Size: 26
Activity: Level 1
i
£2,088.00€2,320.00
Berths available
Short Amalfi Coast Luxury Sailing Holiday
Explore the Amalfi coast and Italian islands under sail from the Bay of Naples with classic yacht Chronos.
Date: 18 Aug 2027
Duration: 4 days
Vessel: Chronos
Where: Italy
Board: Full Board
Group Size: 26
Activity: Level 1
i
£1,664.00€1,840.00
Berths available
Mediterranean Island Escape: Luxury Sailing in Sardinia
Explore the dramatic Italian coast with modern classic yacht Chronos as she sails to explore Sardinia, La Maddalena and Bonifacio.
Date: 28 Aug 2027
Duration: 8 days
Vessel: Chronos
Where: Sardinia, Italy
Board: Full Board
Group Size: 26
Activity: Level 1
i
£3,745.00€4,200.00
Berths available
Mediterranean Island Escape: Luxury Sailing in Sardinia
Explore the dramatic Italian coast with modern classic yacht Chronos as she sails to explore Sardinia, La Maddalena and Bonifacio.
Date: 11 Sep 2027
Duration: 8 days
Vessel: Chronos
Where: Sardinia, Italy
Board: Full Board
Group Size: 26
Activity: Level 1
i
£3,745.00€4,200.00
Berths available
Luxury Yacht Sailing to Cote d’Azur from Sardinia
Explore the dramatic Italian coast with luxury yacht Chronos as she sails to explore Sardinia, Corsica, and Sainte Maxime.
Date: 18 Sep 2027
Duration: 8 days
Vessel: Chronos
Where: Sardinia, Italy / Côte d’Azur
Board: Full Board
Group Size: 26
Activity: Level 1
i
£3,485.00€3,900.00
Berths available
Mediterranean sailing from Croatia to Italy
Join modern classic yacht Kairos on a sailing passage from Croatia to the Sicilian port of Syracuse.
Date: 18 Sep 2027
Duration: 8 days
Vessel: Kairós
Where: Croatia
Board: Full Board
Group Size: 16
Activity: Level 1
i
£2,255.00€2,500.00
Berths available
St Tropez Regatta holiday
Join modern yacht Chronos as she sails the French coast from St. Tropez to Cannes, observing the ‘Les Voiles de St.Tropez’ regatta.
Date: 25 Sep 2027
Duration: 9 days
Vessel: Chronos
Where: Côte d’Azur
Board: Full Board
Group Size: 26
Activity: Level 1
i
£4,275.00€4,800.00
Berths available
Luxury Sailing from Sicily around the Aeolian Islands
Discover the magic of the Sicilian Coast from Syracuse by exploring the Aeolian Islands under sail with the luxury yacht Kairos.
Date: 9 Oct 2027
Duration: 8 days
Vessel: Kairós
Where: Italy
Board: Full Board
Group Size: 16
Activity: Level 1
i
£2,935.00€3,300.00
Berths available
Luxury Sailing from Sicily around the Aeolian Islands
Discover the magic of the Sicilian Coast from Syracuse by exploring the Aeolian Islands under sail with the luxury yacht Kairos.
Date: 16 Oct 2027
Duration: 8 days
Vessel: Kairós
Where: Italy
Board: Full Board
Group Size: 16
Activity: Level 1
i
£2,935.00€3,300.00
Berths available
Luxury sailing from Syracuse to Malta
Sail with luxury yacht Kairos from the ancient port of Syracuse in Sicily to Malta.
Date: 23 Oct 2027
Duration: 6 days
Vessel: Kairós
Where: Sicily / Malta
Board: Full Board
Group Size: 16
£1,995.00€2,200.00
Berths available
