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.
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.
Poros, Greece A Learn-To-Sail Vacation
Join Athens Sailing Academy this fall in Greece and learn to sail while exploring the Aegean. With week-long ASA certification courses, private cabins aboard Jeanneau yachts, English-speaking instructors, and hands-on training in real island conditions, you’ll gain confidence and skills while experiencing the beauty of Poros and the Greek islands. Fall discounts available.
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.
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.
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
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.











