Best Greek Sailing Itineraries, Reviews

SailCheckers regularly asked us why we love sailing in Greece so much and ask for more about the best Greek sailing itineraries.

Before the more practical reasons for explaining our best Greek sailing itineraries, let’s marvel at the allure of Greek Mythology, the stomping ground of Poseidon, of Hercules, Lysander, and other great Hellenic heroes.

The ancient history of the Greek civilisation bursts forth at every turn with ancient ruins and dramatic temples. Spend your time gazing and contemplating of the wonder the philosophers with ideas that frame our modern world. Add the deep iridescent colours of the waters of the Ionian, Aegean, Cyclades and other hidden gems, for those thinking with their heart, there are many reasons to visit and choose one of our best Greek sailing itineraries.

Backing up the stunning waters are the numerous Blue flags you will find on Greek beaches with wonderful swimming and snorkelling opportunities, and with 1,431 to choose from, it will take you a little time to enjoy them all! The Greek weather offers over 250 days of sunshine each year and with access to 5 stunningly different sailing areas, each with their wind pattern, you are sure to find perfect sailing conditions and best Greek sailing itineraries for everyone.

• Ionian Islands
• Dodecanese Islands
• Saronic Islands

• Sporades
• All Around Greece

Wherever your start your sailing holiday in Greece, you will find superb sailing conditions in stunning surroundings, reliable winds, pristine seas, excellent food, a sunny Mediterranean climate and a welcome to match.

Our Highlights. The beautiful and exotic Greek Islands lure droves of tourists every year for some of the best Greek sailing itineraries, making them one of the world’s top travel destinations. Amazing beaches, ancient ruins, excellent cuisine, colourful harbours, breathtaking views and even active volcanoes the Greek islands have it all.

Santorini. Part of the Cyclades group, Santorini is the jewel. It is considered by many the most picturesque islands. Lying in the South Of Greece, is can be a little tricky to access, or, put more accurately, harder to get home if the wind starts to blow form the north.

Mykonos. Also part of the Cyclades, Mykonos features a modern, cosmopolitan society blended with traditional whitewashed houses and maze-like streets.

SailChecker Tip: Enjoy a meal in Little Venice.

Rhodes. Located in the Aegean Sea near the coast of Turkey, Rhodes is the capital and largest island of the Dodecanese archipelago, popular for its great beaches and historical significance.

Corfu. The northernmost of Greece’s Ionian Islands, Corfu was controlled by many foreign powers, notably the Venetians and British, which is reflected in its culture and the architecture on the island. Sporades also will offer you amazing experiences with their crystal clear waters and their natural beauty

Islands. The Dodecanese islands consist of 15 larger islands and over 150 smaller islands, located in the Southeastern Aegean Sea. Within this collection of islands, only 26 are inhabited. The Dodecanese islands cover an area of 1,048 square miles, which makes it one of our best Greek sailing itineraries.

Greek Sailing Itineraries. The Dodecanese is one of our favourite best Greek sailing itineraries, and it’s easy to discover why these islands are often referred to as the ‘sunniest corner of Greece’, thanks to their crystal clear turquoise waters, sandy and stone beaches, stunning archaeological landmarks, and traditional settlements. There are also unique Byzantine and medieval monuments which cover a large number of the islands.

Places To Discover. The Saronic islands are some of our favourite islands to visit, which is why we have included them in our best Greek sailing itineraries list. Some of the best islands to visit are listed below.

• Poros
• Tselevinia
• Dokos
• Heli Beach
• Spetses Island
• Hydra
• Kanakia
• Aigina

Sporades. The Sporades consist of 24 islands in the Aegean Sea. 4 of these islands are completely free of human residents, you’ll only find gorgeous scenery and empty beaches. Much of the area is considered a national park, and guests are encouraged to explore the area while leaving things carefully preserved behind them. The largest and most populated island is Skopelos, which has several villages and an opportunity to experience island life.

Greek Sailing Itineraries. The archipelago is also home to several historic sites. Once the home of neolithic peoples to members of the Ottoman Empire, you’ll find sunken cities, ruins, and almost-forgotten monasteries ready to visit and discover. The Sporades offer a bit of adventure and a chance to rest from modern life. This is a slightly more challenging of our best Greek sailing itineraries for those with a few sailing trips already under their belt (Level 3).

Greek wine is much-maligned the world over, yet there’s so much more to Greek wine than adodgy retsina. If you do get the opportunity, you should visit at least one vineyard during your stay.

SailChecker Tip: The image is from a traditional winery in Samos, why not drop by where you will be made very welcome.

You can find traditional, family-held wineries all around the greek islands.