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Sail the turquoise waters of the world from the Greek & Italian Mediterranean to the Bahamas to Morocco and the Canary Islands, the Grenadines, and the Caribbean. Snorkeling, kayaking, visiting archaeological sites, and simply cruising at the leisure of the wind as it blows the sails are all activities you might enjoy on your classic sailing cruise aboard a luxurious schooner. With multiple restaurants, bars, lounges, and social areas plus comfortable rooms, these cruises capture the essence of elegance on the high seas. Let us know when you're ready to start planning your sailing adventure!

Top 10 Sailing Schooner Cruises & Tours for 2025-2026

Best Sailing Schooner Trips in the Mediterranean for 2025-2026

Trip Name From Days Next Departure Summary
Sailing the Greek Islands $13,995 12 Aug 29, 2026 Set sail on a 12-day cruise aboard the Douglas Mawson through Greece's stunning islands, experiencing vibrant villages and rich Mediterranean culture. Discover historical gems like Rhodes, Santorini, and Ephesus while starting your adventure in Athens.
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Isle of Beauty, Italian shores & Malta $7,990 11 Aug 19, 2026 Embark on this 11-day cruise across the Mediterranean from Nice to Valletta aboard Le Dumont-d'Urville. Explore Corsica’s charming ports, Sicily’s historical treasures, and the natural beauty of the Aeolian Islands. Visit iconic landmarks like the Calvi Citadel, Portofino’s harbor, and Lipari’s obsidian quarries.
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Epicurean Delights of Sicily and the Adriatic Coast of Italy $9,920 9 Jun 10, 2025 Embark on a 9-day Le Bougainville trip through Sicily and Italy’s Adriatic coast, visiting UNESCO sites like Valletta, Syracuse, and Venice. Explore ancient ruins, Baroque cities, and medieval towns, while enjoying local wines, cheeses, and dishes prepared by chef Denny Imbroisi.
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Sailing the Greek Isles $12,709 8 Jun 05, 2025 Explore the sun-kissed Greek Isles on this 8 luxury cruise aboard the Sea Cloud, a 58-guest sailboat. Each stop on this round trip cruise from Piraeus is brimming with activities, such as exploring the sanctuary ruins of Delos, the iconic cliffside villages of Santorini, and the Classical Greek culture and mythology.
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Greece & Turkey: Turkish Delight $11,795 13 Aug 19, 2026 Set sail on a 13-day cruise aboard the Douglas Mawson to explore Turkey and the Greek islands. Experience vibrant Istanbul, the ruins of Ephesus, the beauty of Bodrum, and honor the sacrifices at Gallipoli, all while journeying through powerful historical narratives.
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From the City of the Gods to the Dalmatian Coast $6,230 9 Aug 10, 2025 Embark on a 9-day From the City of the Gods to the Dalmatian Coast cruise aboard the Le Dumont-d'Urville from Athens to Dubrovnik. Discover Nafplion’s hilltop fortress and scenic promenades before visiting the legendary theater of Epidaurus. Explore Kythira’s charming villages, Pylos’ Venetian castles, and Zakynthos’ famous shipwreck beach.
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Longing for La Dolce Vita $8,490 8 Sep 08, 2025 Embark on an 8-day "Longing for La Dolce Vita" cruise aboard the Sea Cloud Spirit. Begin in Taormina, a town known for its blend of cultures and varied cuisine. Explore Palermo and discover its historic palazzi and gold mosaics, then head to Lipari, an island with volcanic landscapes and a lively harbor town. The trip concludes in Amalfi.
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Grand Voyage: Venice to Rome $4,500 17 Jul 03, 2025 Embark on a 17-day Grand Voyage from Venice to Rome aboard the Star Flyer. Experience the romantic charm of Venice, the historic allure of Dubrovnik, and the stunning beauty of Sicily. Discover unspoiled beaches, medieval towns, and cultural treasures across Croatia, Montenegro, and Italy.
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Grand Voyage: Athens to Athens $3,970 15 Aug 30, 2025 Embark on a 15-day cruise aboard the Star Clipper, sailing through Greece and Turkey, from the Acropolis of Pergamon to the vibrant shores of Mykonos. Discover breathtaking landscapes, ancient ruins, and rich culture while enjoying adventure and relaxation at sea.
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Grand Voyage: Cannes to Rome $3,040 10 Jun 05, 2025 Embark on a 10-day cruise aboard the Royal Clipper through glamorous ports of the Mediterranean, including Cannes, Corsica, and Portofino. Enjoy luxury, culture, and stunning scenery on this unforgettable journey.
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Canary Islands & Morocco Sailing Cruises for 2025-2026

Sailing Schooner Cruises of the Bahamas & Caribbean for 2025-2026

Trip Name From Days Next Departure Summary
Discover Eastern Caribbean & Grenadines $21,340 15 Dec 06, 2025 Set sail on a 15-day cruise to explore unspoiled beaches, vibrant coral reefs, and captivating island cultures. Experience the genuine warmth of the locals as you hop between tropical paradises, creating unforgettable memories aboard the Emerald Sakara.
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Eastern Caribbean with St. Barths $9,990 8 Dec 06, 2026 Set sail on an 8-day cruise aboard the Emerald Azzurra, exploring idyllic beaches and vibrant coral reefs—Island-hop through diverse cultures, with the warmth of the locals adding to your luxurious yacht experience.
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Cruising the Leeward Islands $9,990 8 Dec 13, 2026 Set sail on an 8-day Caribbean cruise with Emerald Azzurra. Start in Marigot, then visit Anguilla’s coral beaches, Virgin Gorda’s Baths, Jost Van Dyke’s Bubbly Pool, and Anegada’s sandy shores. Explore Saba’s trails and Bonaire’s marine life before ending in Gustavia. Enjoy a luxury cruise with varied landscapes and activities.
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Eastern Caribbean with St. Barths $9,990 8 Dec 20, 2026 Set sail on an 8-day cruise aboard the Emerald Azzura, island-hopping through vibrant cultures and breathtaking landscapes. Discover pristine beaches, vivid coral reefs, and the genuine warmth of locals while enjoying the elegance of a luxury yacht experience.
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Eastern Caribbean with St. Barths $7,990 8 Dec 06, 2025 Embark on an 8-day Caribbean cruise aboard Emerald Sakara. Discover Anguilla’s pristine beaches, Gustavia’s vibrant streets, Nevis' historic charm, Saint Kitts’ stunning nature, Falmouth Harbour’s historical docks, Îles des Saintes’ picturesque islands, and Barbados’ lively culture. Experience crystal-clear waters, vibrant local culture, and luxurious amenities throughout your cruise
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Eastern Caribbean with St. Barths $7,990 8 Nov 22, 2025 Set sail on an 8-day cruise aboard the Emerald Sakara, exploring idyllic beaches and vibrant coral reefs—Island-hop through diverse cultures, with the warmth of the locals adding to your luxurious yacht experience.
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Caribbean Yachting Hideaways $8,390 8 Dec 20, 2025 Set sail on an 8-day cruise from San Juan to St. John aboard the Emerald Azzurra, exploring stunning beaches and vibrant island towns. Visit highlights like Culebra, Vieques, and Saint Barthelemy while enjoying premium comfort and seamless access to diverse ports.
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Caribbean Yachting Discovery $7,990 8 Dec 13, 2025 Set sail on an 8-day cruise aboard the Emerald Azzurra, uncovering pristine beaches and vibrant coral reefs while island-hopping through a tapestry of diverse cultures. Let the genuine warmth of the locals add a personal touch to your luxurious yacht adventure.
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Caribbean Yachting Discovery $8,390 8 Mar 07, 2026 Embark on an 8-day Caribbean cruise aboard Emerald Azzurra from Antigua to St. Thomas. Explore vibrant ports like Barbuda, Illes des Saintes, and Virgin Gorda. Discover unique sites such as Norman Island’s caves and the markets of Guadeloupe. Travel aboard a luxury yacht, exploring beaches, history, and local culture at each stop.
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Caribbean Sojourn $11,990 7 Jan 03, 2027 Embark on a 7-day Caribbean adventure aboard the Emerald Azzurra. Set sail from Barbados and explore diverse islands including Soufriere’s mud baths, Falmouth Harbor’s historic dockyard, Iles des Saintes’ picturesque beaches, Gustavia’s vibrant streets, and Marigot’s charming French town.
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