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
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.
MALLORCA A GUIDED FLOTILLA
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.
Amalfi Coast A GUIDED FLOTILLA
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.
Corfu & The North Ionian Sea, Greece A Learn-To-Sail Vacation
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.
Corfu & Paxos Islands, Greece A Learn-To-Sail Vacation
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.
Lefkas, Ithaca, & Kefalonia, Greece A Catamaran Learn-To-Sail Vacation
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.
Central Ionian Sea, Greece A Learn-To-Sail Vacation
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.
Athens & the Saronic Gulf, Greece A Guided Flotilla
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.
Gulf of Fethiye, Turkey A Guided Flotilla
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.
Whitecaps Volos Kickoff – Sail Greece A Learn-To-Sail Vacation
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.
Islands of North Adriatic A Learn-To-Sail Vacation
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.
Poros, Greece A Learn-To-Sail Vacation
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.
Women-Only Classes in Poros, Greece A Learn-To-Sail Vacation
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.
Spring Mile Builder to Chios A Learn-To-Sail Vacation
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.
EXPLORE CROATIA ABOARD CATALEYA A LUXURY CRUISE
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.
Eclipse on the Med, Mallorca, Spain A Guided Flotilla
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
Food & Wine in Dubrovnik, Croatia A Guided Flotilla
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.
Central Dalmatian Islands, Croatia A Guided Flotilla
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.
SOUTH OF FRANCE & MALLORCA ABOARD CHRONOS A LUXURY CRUISE
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.
EXPLORE MALLORCA ABOARD CHRONOS A LUXURY CRUISE
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.




















