Greece Sailing Trips & Itineraries

Explore 8 sailing trips designed by local kimkim specialists to get ideas for your trip to Greece.

The Greek isles encompass so much more than just Santorini and Crete. You could design an epic sailing holiday that will take you around the Ionian Sea to islands like Lefkas, which are home to ancient Roman ruins. Then there’s the Aegean Sea and its unforgettable islands, like Kea and Milos, which boast postcard beaches and the ruins of old temples. And if you do want the quintessential Greek-island experience, then perhaps embark on a luxury sailing cruise around the famous beaches of Naxos and Mykonos on a private yacht.

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Sailing the Cyclades
Map of Sailing the Greek Cyclades Islands - 8 Days
Sailing the Greek Cyclades Islands - 8 Days

Sailing the Greek islands for a week sounds amazing for good reason. Board a catamaran with an experienced crew to hop from island to stunning island in the Cyclades. Along the way, explore the best of Mykonos and watch the sunset from Santorini, see ancient ruins, and swim in the azure Aegean waters before bedding down in your boat each night.

A secluded cove in the Ionian sea, accessible only by boat
Map of Sail the Ionian Sea from Corfu - 8 Days
Sail the Ionian Sea from Corfu - 8 Days

If you love sunny days, turquoise waters, and relaxing beaches, this tour's for you! Sweep from coastal town to coastal town as you travel by yacht from Corfu to Syvota, Paxos, and more. Explore ancient ruins, sun yourself on Ionian beaches, and fall in love with everything Greece has to offer.

Mykonos harbor
Map of Luxury Cyclades Yacht Cruise - 9 Days
Luxury Cyclades Yacht Cruise - 9 Days

Cruise like a celebrity through the glittering waters of the Cyclades on this nine-day itinerary.  The Cyclades are some of the most quintessential Greek islands, and you'll see seven of them from the decks of your yacht, along with plenty of time to explore onshore. From lesser-known spots like beach-lined Milos and petite Antiparos to favorites like bustling Naxos and cosmopolitan Mykonos, you'll scope out this island chain in style.

Mykonos, Greece
Sailing the Greek Cyclades: Athens, Mykonos, Paros - 10 Days

Best for those interested in seeing Greece by boat, this sailing adventure combines bustling and ancient Athens with some of the country's most beautiful islands: the Cyclades. Set on a yacht, you'll sail the turquoise waters of the Aegean Sea in search of the region's rich heritage, including gorgeous beaches, iconic windmills, exotic plant life, and beautiful sunsets. The days are yours to indulge in rich, local cuisine, as well as discover archaeological sites, step back in time while meandering small villages, and enjoy some of the best nightlife in Greece.

The Cyclades Islands of Greece
Sailing the Greek Cyclades: Paros, Mykonos, Serifos - 8 Days

As the ultimate sailing adventure through Greece's coveted Cyclades Islands, this tour combines bustling city life with tranquil villages nestled in the Aegean Sea. From some of Europe's best nightlife to humble fishing towns and secluded beaches, travelers will enjoy Greece's rich and varied heritage. Enjoy sunsets and local seafood while discovering important and ancient archeological sites, all from the comfort of a private yacht.

Beach off of Milos
Map of Sailing Holiday in the Aegean - 9 Days
Sailing Holiday in the Aegean - 9 Days

Channel the spirit of some of Greece's most famous tales as you sail through the Aegean on this nine-day itinerary. Start off by paying the proper tribute at the Temple of Poseidon before you start on your way to Kea, followed by the villages of Kythnos. Visit the capital of the Cyclades on Syros and the home of the Cyclops on Serifos, then search for the Venus de Milo's cousin on Milos before you end your trip on the double beach of Kolona.

Boats off Moni island
Map of Sailing Holiday in the Saronic Gulf - 9 Days
Sailing Holiday in the Saronic Gulf - 9 Days

Spend nine days getting your sea legs with this sailing itinerary. Once believed to be one of six entrances to the Underworld, the Saronic Gulf is now one of the most popular yacht spots in Greece. You'll travel to a new island each day, taking in harbor towns and historic temples and churches, sampling island specialties, and enjoying the sea breeze.

Aegina island
Map of Greek Mainland & Saronic Islands Sailing Trip - 10 Days
Greek Mainland & Saronic Islands Sailing Trip - 10 Days

Discover the storied heart of Ancient Greece in this 10-day escorted journey. Begin your trip in Athens before taking an idyllic sail around the Saronic Islands. Spend three days island-hopping, enjoying small seaside towns, beautiful beaches, and a relaxed ambiance. Once back on land, head to the Peloponnese peninsula, home of the original Olympic Games and the famously warring cities of Sparta, Corinth, and Argos. Your journey ends where it began, with a bike tour through the iconic capital city.