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

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.

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MALLORCA A GUIDED FLOTILLA

Nautilus Sailing
Availability : May 23 - 30, 2026

Sailing the coastline of Mallorca is a dreamlike journey through the heart of the Mediterranean. As the largest of Spain’s Balearic Islands, Mallorca offers an irresistible blend of rugged coastlines, serene turquoise coves, charming seaside villages, and rich Spanish culture. The island is a sailor’s paradise—calm waters, steady breezes, and countless hidden anchorages create the perfect conditions for a relaxed and unforgettable voyage. Whether you’re exploring remote natural parks, enjoying a beachside paella, or sipping wine beneath the stars, Mallorca invites you to experience sailing at its most beautiful.

From$3,750
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Amalfi Coast A GUIDED FLOTILLA

Whitecaps Sailing
Availability : May 23 - 30, 2026

Set your course for a week of Italian magic on the Amalfi Coast Flotilla. This unforgettable journey blends world-class sailing with iconic stops in Capri, Positano, and Procida. Enjoy crystal-clear waters, gourmet cuisine, and sun-soaked coastlines aboard a luxurious catamaran, all with the perfect balance of freedom and expert support. Limited to just three boats, this is small-group adventure at its finest. Reserve your cabin today and sail Italy like never before.

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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 May - 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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Corfu LTSV Fair Winds Sailing

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

Fair Winds Sailing Greece
Availability : Various Dates May - 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.

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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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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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Saronic Gulf greece

Athens & the Saronic Gulf, Greece A Guided Flotilla

Whitecaps Sailing
Availability : May 30 - Jun 06, 2026

Set sail from Athens on a 7-night flotilla through the stunning Saronic Gulf. Cruise turquoise waters, explore charming island harbors, and swim in secluded coves while enjoying the perfect balance of independence and expert guidance. Skipper your own yacht or join by cabin aboard a fully equipped monohull or catamaran. With daily briefings, on-water support, and unforgettable Greek sunsets, this adventure blends hands-on sailing, culture, cuisine, and community.

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Gulf of Fethiye Turkey

Gulf of Fethiye, Turkey A Guided Flotilla

Whitecaps Sailing
Availability : Jun 06 - 13, 2026

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.

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Whitecaps Volos Kickoff - Sail Greece

Whitecaps Volos Kickoff – Sail Greece A Learn-To-Sail Vacation

Whitecaps Sailing School
Availability : Jun 06 - 13 & Jun 27 - Jul 04, 2026
101 / 103 / 104

Set sail with Whitecaps Sailing in Volos, Greece, and earn your ASA 101–104 certifications while exploring the tranquil Sporades Islands. This hands-on sailing adventure blends expert instruction with the beauty and culture of coastal Greece. Perfect for beginners or sailors advancing their skills.

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North Adriatic Islands Learn-To-Sail Vacation

Islands of North Adriatic A Learn-To-Sail Vacation

Annapolis Sailing School
Availability : May 16 & Jun 20, 2026
101 / 103 / 104

Experience the beauty of the Adriatic Sea as you sail along Croatia’s breathtaking coastline, famous for its turquoise waters, charming islands, and vibrant seaside towns. Discover hidden coves, ancient ports, and picturesque villages while learning to sail with experienced local instructors. This program combines hands-on training with leisure, allowing you to relax, explore, and gain valuable sailing experience aboard a comfortable monohull or catamaran. From Rijeka to Rab, every stop offers a perfect blend of culture, nature, and adventure.

From$2,100
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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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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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Spring Mile Builder to Chios A Learn-To-Sail Vacation

Athens Sailing Academy
Availability : May 02 - 09, 2026
104 / 105 / 106 / 114 / IPC

Spring Mile Builder is an intensive, live-aboard sailing experience designed to fast-track your skills through real offshore miles. Sail day and night in the Aegean, rotate through active crew roles, build confidence on longer passages, and log qualifying miles toward ASA certifications—all while exploring the Greek Islands under expert instruction.

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LIMITED CABINS AVAILABLE

EXPLORE CROATIA ABOARD CATALEYA A LUXURY CRUISE

American Sailing
Availability : May/Sep 2026

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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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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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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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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SOUTH OF FRANCE & MALLORCA ABOARD CHRONOS A LUXURY CRUISE

American Sailing
Availability : October 2026

Your journey begins in the glamorous port of St. Tropez, known for its luxury yachts, vibrant nightlife, and charming old town. As you set sail from this iconic French Riviera destination, the Mediterranean’s turquoise waters will guide you toward Marseille. Along the way, you can enjoy the stunning coastal landscapes, with opportunities for swimming in secluded coves or relaxing on deck.

From$4,250
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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.

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