Sicily and the Aeolian Islands Schedule

Sicily and the Aeolian Islands combine volcanic landscapes, crystal-clear waters, and charming villages. Sail past smouldering Stromboli, explore lava-formed coves, dive into secluded bays, and wander historic streets. Dolphins, whales, and coral reefs add to the experience, while local food, wine, and culture make every stop unforgettable.
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We have found 9 voyages with berths available.

Tall ship sailing through the Messina Straits from Malta to Italy
Comino, Malta
Florette under full sail
Italy Sicily street
Guests Pulling Ropes on board Florette
Florette anchored with guests swimming
Church in Mellieha, Malta, Europe, Mediterranean

Tall ship sailing through the Messina Straits from Malta to Italy

Join traditional tall ship Florette for a two week island-hopping voyage from Malta through the Messina Straits to Italy.
Date: 27 Jun 2026
Duration: 15 days
Vessel: Florette
Where: Malta/Italy
Board: Half Board
Group Size: 22
Activity: Level 2
i
£1,335.00€1,480.00
Berths available
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Mediterranean Sailing from Malta to Italy with Florette
Comino, Malta
Florette Sailing Aeolian Islands
Guests on bowsprit of Florette
Guests hoisting sails on Florette
Italy Sicily street
Breakfast on Deck Florette
Florette anchored with guests swimming
Twin Cabin on Florette
Young Sailors Discount

Mediterranean Sailing from Malta to Italy with Florette

Island hop with traditional tall ship Florette for Mediterranean sailing from Malta to Italy.
Date: 1 Jul 2026
Duration: 11 days
Vessel: Florette
Where: Malta/Italy
Board: Half Board
Group Size: 22
Activity: Level 2
i
£900.00€980.00
Limited berths
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Luxury Distance Sailing from Mallorca to Sicily
Kairos Resized Final
Mallorca spain sailing
Crew member winching sails on board SC Chronos Rhea Kairos
Salina aeolian islands italy
Kairos guest on deck underway sailing in the BVIs British Virgin Islands at helm
Kairos anchored in calm waters Greece

Luxury Distance Sailing from Mallorca to Sicily

Join yacht Kairos on the island of Mallorca for a distance sailing cruise to Sardinia and the Aeolian Islands before finishing in Sicily.
Date: 15 Aug 2026
Duration: 9 days
Vessel: Kairós
Where: Spain/Italy
Board: Full Board
Group Size: 16
Activity: Level 2
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£2,480.00€2,900.00
Berths available
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Historic Tall Ship Sailing in Italy’s Aeolian Islands
Florette Sailing Aeolian Islands
Aeolian Islands View of Vulcano
Florette guests diving bowsprit
Island of Lipari Aeolian Islands
Florette bow sailing
salina aeolian islands florette resized

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
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£1,250.00€1,380.00
Limited berths
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Historic Tall Ship Sailing in Italy’s Aeolian Islands
Florette Sailing Aeolian Islands
Aeolian Islands View of Vulcano
Florette guests diving bowsprit
Island of Lipari Aeolian Islands
Florette bow sailing
salina aeolian islands florette resized

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
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Guided Hiking & Sailing in the Aeolian Islands
Florette in full sail with sunshine behind
View from the island of Vulcano in the Aeolian Islands
Florette guests on the bowsprit
stromboli aeolian islands florette vulcano
Florette anchored in Lipari at night, Aeolian Islands
Aeolian Islands View of Vulcano
Florette bow sailing

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
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Sailing Holiday in Southern Italy
Chronos yacht underway full sail sailing off coast
Italy Sicily Cerfalu
Chronos guests onboard relaxing on deck luxury yacht
Taormina Italy
Chronos Amalfi coast
Guests enjoying meal on board SC Chronos Rhea
Chronos sunny deck onboard underway sailing in Caribbean
2027

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
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Mediterranean sailing from Croatia to Italy
Kairos yacht underway sailing
Kairos view on deck under sail
Aerial view of the bay of Vis, Croatia
Kairos anchored with guest paddleboarding in the Mediterranean
Town of Stari Grad, Hvar Island, Croatia
Kairos crew member on board
2027

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
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Luxury sailing from Syracuse to Malta
KAIROS under sail
bay in Comino, Malta
KAIROS on deck
KAIROS from bowsprit
Church in Mellieha, Malta, Europe, Mediterranean
KAIROS from the air
2027

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
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