MEDITERRANEAN

ENJOY A SAILING VACATION IN THE MEDITERRANEAN

The Mediterranean is renowned for its beautiful weather and tideless waters, making it the ideal destination for a sailing vacation. Exploring the area by boat gives you access to some amazing less-traveled areas. There are also a lot of cultural attractions and delicious food to enjoy.

Popular Mediterranean Sailing Destinations: Croatia | Italy | Greece | Spain | Turkey

Poros, Greece

Poros, Greece A Learn-To-Sail Vacation

Athens Sailing Academy
Availability : Jul 01 - 30, 2026
101 / 103 / 104 / 105 / 106

As Europe’s oldest ASA-certified sailing school, Athens Sailing Academy offers world-class instruction in Greece’s stunning waters. Train in Poros during summer, where sunshine, warm seas, and steady winds create the perfect learning conditions, or at our Athens headquarters year round. Our experienced English-speaking instructors share their passion for sailing and deep local knowledge to help you master the art of confident, safe cruising through the Greek islands.

From$1,850
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Barcelona, Spain A Learn-To-Sail Vacation

Red Sky Sailing Barcelona
Availability : Jul 18-24, Jul 25-31, Aug 01-07, & Aug 15-21, 2026
101 / 103 / 104

Barcelona Sailing Week offers a one week learn to sail experience where students earn ASA 101, 103, and 104 certifications while sailing the Mediterranean by day and enjoying the energy of Barcelona each night. Based out of Port Olímpic, the program combines consistent sailing conditions, hands on instruction, and a coastal passage to Sitges with the flexibility to stay aboard or in a hotel, creating a balanced experience of skill building, adventure, and city life.

From$2,340
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Corfu LTSV Fair Winds Sailing

Corfu & Paxos Islands, Greece A Learn-To-Sail Vacation

Fair Winds Sailing Greece
Availability : Various Dates July - September, 2026
101 / 102 / 103 / 104 / 105 / 106 / 114 / 116 / 118

Sail the beautiful waters of Corfu and Paxos Islands with Fair Winds Sailing Greece. Departing from historic Mandraki Port, this all-inclusive Learn-to-Sail adventure blends hands-on training with island hopping, swimming in turquoise bays, and exploring charming harbors, all led by Captain Dimitris Bampakos, a seasoned Greek Navy officer and ASA Senior Master Instructor.

From$1,990
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Corfu & North Ionian Sea Learn-to-Sail Vacation with Fair Winds Sailing

Corfu & The North Ionian Sea, Greece A Learn-To-Sail Vacation

Fair Winds Sailing Greece
Availability : Various Dates July - October, 2026
101 / 102 / 103 / 104 / 105 / 106 / 114 / 116 / 118

Sail through the stunning waters of Corfu and the North Ionian Sea with Fair Winds Sailing Greece. This all-inclusive adventure blends hands-on instruction with island hopping, swimming in crystal bays, and exploring charming coastal villages. Learn from Captain Dimitris Bampakos, a seasoned Greek Navy officer and master ASA instructor, as you earn certifications and experience the magic of Greece. Where every day brings new horizons and memories.

From$1,990
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Eclipse on the Med, Mallorca, Spain A Guided Flotilla

Whitecaps Sailing
Availability : Aug 08 - 15, 2026

Experience the magic of a total solar eclipse as it unfolds above the waters of the Mediterranean—an awe-inspiring event witnessed from the deck of a sailing yacht off the coast of Mallorca. This once-in-a-lifetime adventure combines the wonder of the cosmos with the natural beauty, rich history, and coastal charm of one of Spain’s most stunning islands

From$3,150
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Greece Value Trip

A Greece VALUE Trip Aboard Artemis A Value Cruise

American Sailing
Availability : Aug 22 - 29, 2026

Set sail on the Harmony Cruise, an affordable 8-day island-hopping sailing adventure through the stunning Aegean Sea. Departing round-trip from the Athens area, this relaxed, social voyage blends swim stops, historic harbor towns, and open-water cruising aboard a traditional Greek gulet. Designed for travelers who want the magic of exploring Greece by boat without the high price of luxury cruises, this journey offers authentic sailing, beautiful coastal scenery, and unforgettable moments at sea.

From$1,900
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Food & Wine in Dubrovnik, Croatia A Guided Flotilla

Whitecaps Sailing
Availability : Aug 29 - Sep 05, 2026

Sail Croatia’s stunning Dalmatian Coast on a week-long GASTRO-SAIL Food & Wine Flotilla from Dubrovnik. Explore Korčula, Mljet, and Ston while visiting family-run wineries, oyster farms, and waterfront restaurants accessible only by boat. Swim in crystal-clear Adriatic waters, enjoy relaxed island sailing, and experience the rich flavors and culture of coastal Croatia alongside fellow food and wine lovers.

From$2,550
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Costa Dorada, Spain A Learn-To-Sail Vacation

Red Sky Sailing Barcelona
Availability : Aug 29-Sep 04, Sep 05-11, Oct 10-16, & Oct 24-30, 2026
101 / 103 / 104

Sail the Costa Dorada on a 7-day coastal passage from Barcelona, exploring historic ports, clear-water coves, and vibrant seaside towns. This hands-on itinerary combines real-world sailing with ASA 101, 103, and 104 training, building skills progressively each day. With calm Mediterranean conditions, scenic anchorages, and unforgettable evenings ashore, it’s the ideal blend of certification, adventure, and culture.

From$2,340
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Sardinia, Maddalena Archipelago A GUIDED FLOTILLA

Whitecaps Sailing
Availability : September 05–12, 2026

Sail through Sardinia’s Emerald Coast, the Maddalena Archipelago, and Bonifacio, Corsica on a weeklong Mediterranean flotilla filled with turquoise waters, hidden coves, charming ports, local cuisine, and unforgettable island scenery.

From$2,500
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Womens Only Poros Greece learn to sail vacation

Women-Only Classes in Poros, Greece A Learn-To-Sail Vacation

Athens Sailing Academy
Availability : Sep 12 - 19, & Sep 26 - Oct 03, 2026
101 / 103 / 104 / 105 / 106

Discover Women of the Wind, an all-female ASA sailing experience in Greece where women learn, grow, and take the helm with confidence. Sail through the Greek islands, build real seamanship skills, earn certification, and join a supportive community of passionate women sailors.

From$1,900
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central dalmatian islands

Central Dalmatian Islands, Croatia A Guided Flotilla

Whitecaps Sailing
Availability : Sep 12 - Sep 19, 2026

Sail Croatia’s Dalmatian Coast on a week-long flotilla through turquoise waters, historic towns, and island harbors. Departing from Trogir, this classic itinerary explores Vis, Hvar, and more with relaxed sailing, daily briefings, and the camaraderie of a welcoming sailing community.

From$2,525
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Lefkas, Ithaca, & Kefalonia, Greece A Catamaran Learn-To-Sail Vacation

Fair Winds Sailing Greece
Availability : Various Dates September - October, 2026
103 / 104 / 114 / 118

Sail through Greece’s breathtaking Ionian Sea, where calm maistro winds, turquoise waters, and lush islands set the stage for an unforgettable adventure. Explore the captivating beauty of Lefkas, Ithaca, and Kefalonia, discovering historic towns, hidden coves, and seaside tavernas that make these legendary islands some of the world’s most cherished sailing destinations.

From$2,490
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LIMITED CABINS AVAILABLE

EXPLORE CROATIA ABOARD CATALEYA A LUXURY CRUISE

American Sailing
Availability : Sep 2026 & May/Sep 2027

Welcome aboard Cataleya a 30 meter luxury sailing yacht which will be your home for 8 days as you explore the Dalmation coast of Croatia. This trip will include stops in Split, Hvar, Korcula as well as a few anchorages that are the secrets of the captain and the crew. Join us on a once-in-a-lifetime sailing vacation.

From$3,100
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Costa Brava, Spain A Learn-To-Sail Vacation

Red Sky Sailing Barcelona
Availability : Sep 05-11, Sep 19-25, Sep 26-Oct 02, & Oct 17-23, 2026
101 / 103 / 104

Sail the Costa Brava from Barcelona and experience real Mediterranean conditions, dramatic cliffs, and historic coastal towns. This hands-on itinerary combines ASA 101, 103, and 104 training with open-water passages and variable winds, building true confidence and skill. By the end of the week, students earn three certifications and are ready to charter anywhere in the Mediterranean.

From$2,340
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Greek Island Hopper A Guided Flotilla

Fair Winds Sailing Greece
Availability : Sep 27 - Oct 03, 2026

Set sail on the Greek Island Hopper Flotilla, hosted by Fair Winds Sailing Greece, and experience the beauty of Corfu and the surrounding Ionian islands. Guided by local captains, you’ll visit favorite anchorages, UNESCO World Heritage sites, and charming island towns while enjoying the perfect blend of sailing, culture, and relaxation. Sail aboard modern monohulls or catamarans, share meals and onshore excursions with fellow sailors, and discover Greece as seen through the eyes of those who know it best.

From$2,250
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Central Ionian Sea, Greece A Learn-To-Sail Vacation

Fair Winds Sailing Greece
Availability : Various Dates May - October, 2026
103 / 104 / 114 / 118

Embark on an unforgettable Catamaran Learn to Sail Vacation with Fair Winds Sailing Greece, an American Sailing affiliate. Departing from Lefkas Marina, this adventure takes you through the Central Ionian Sea, a breathtaking region celebrated for its turquoise waters, gentle “maistro” winds, and lush green islands steeped in history and charm.

From$2,490
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Barcolana Regatta from Croatia to Italy A Guided Flotilla

Adriatic Sailing Academy
Availability : October 07 - 13, 2026

Sail the Adriatic on an unforgettable Croatia-to-Italy flotilla culminating in the legendary Barcolana Regatta in Trieste. Led by American Sailing certified instructor Fabio Matijević, this experience combines scenic coastal passages, historic ports, local culture, mini regatta training, and the excitement of racing alongside hundreds of sailors in one of the world’s largest sailing events. Perfect for both experienced and newer sailors, with bareboat, skippered, private, and certification options available.

From$2,600
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NEW

EXPLORE MALLORCA ABOARD CHRONOS A LUXURY CRUISE

American Sailing
Availability : October 2026

Embark on a 8-day luxury sailing adventure aboard Chronos Yacht, exploring Mallorca to Menorca with American Sailing. Enjoy personalized service, secluded coves, and stunning coastlines with a small, passionate group. This intimate voyage offers full-board luxury, breathtaking views, and unique experiences in the heart of the Balearic Islands. Set sail for an unforgettable journey this fall.

From$4,250
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Amalfi Coast A GUIDED FLOTILLA

Whitecaps Sailing
Availability : May 29–June 05, 2027

Experience the beauty of Italy’s Amalfi Coast on this unforgettable flotilla sailing vacation. Cruise alongside fellow sailors as you explore iconic destinations like Capri, Positano, and Procida, discover charming coastal villages, swim in crystal-clear waters, and enjoy authentic Italian cuisine. With expert guidance, a flexible itinerary, and the camaraderie of a small flotilla limited to just three catamarans, this is the perfect way to experience la dolce vita by sea.

From$2,950
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NEW
Sicily Italy

Experience Sicily ABOARD RHEA A LUXURY CRUISE

American Sailing
Availability : May 2027

Experience the magic of Sicily on a breathtaking sailing journey through the Aeolian Islands. Departing from Palermo, this refined Mediterranean voyage blends volcanic landscapes, turquoise swim stops, charming coastal villages, and unforgettable nights under the stars. Designed for travelers seeking both adventure and elegance, this weeklong escape offers an immersive taste of Italy’s culture, cuisine, and timeless rhythm of life at sea.

From$4,750
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Gulf of Fethiye Turkey

Gulf of Fethiye, Turkey A Guided Flotilla

Whitecaps Sailing
Availability : Jun 19 - 26, 2027

Explore the breathtaking southwestern coast of Türkiye on a 7-night sailing flotilla through the stunning Bay of Fethiye. With crystal-clear waters, reliable Mediterranean winds, and secluded coves accessible only by sea, this region offers the perfect blend of relaxed cruising and spirited sailing. Each day brings ancient Lycian ruins, dramatic landscapes like Butterfly Valley, charming harbor towns such as Göcek, and unforgettable sunsets at anchor.

From$2,595
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NEW

Sail Sardinia & Corsica Aboard Chronos A Luxury Cruise

American Sailing
Availability : September 2027

Sardinia & Corsica Aboard CHRONOS is a luxurious Mediterranean sailing adventure through the breathtaking coastlines of Sardinia and Corsica aboard a stunning 54 meter classic yacht. Explore the crystal clear waters of Costa Smeralda, La Maddalena National Park, and the legendary harbor town of Bonifacio while enjoying elegant dining, spacious decks, and unforgettable sunsets under sail. With only 12 cabins available, this exclusive September 4–11, 2027 voyage offers the perfect blend of authentic sailing, relaxed luxury, and timeless Mediterranean charm.

From$4,750
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