Exploring the Greek Islands by Sailboat
Exploring the Greek Islands by Sailboat

Embark on an unforgettable adventure and explore the stunning Greek Islands by sailboat. Discover the rich history, breathtaking landscapes, and warm hospitality of this unique destination.

Exploring the Greek Islands by Sailboat

The Greek Islands are a dream destination for many sailors, offering a unique blend of ancient history, stunning natural beauty, and vibrant local culture. With over 6,000 islands and islets scattered across the Aegean and Ionian Seas, there is no shortage of destinations to explore and adventures to be had. In this comprehensive guide, we will delve into the world of sailing the Greek Islands, providing practical advice, insider tips, and personal stories to help you plan your own unforgettable voyage.

Table of Contents

Why Sail the Greek Islands?

The Greek Islands offer a unique combination of factors that make them an ideal destination for sailing enthusiasts:

  • Rich history and culture: Greece is the birthplace of Western civilization, and its islands are steeped in ancient history. From the ruins of the Parthenon in Athens to the Palace of Knossos on Crete, there is no shortage of fascinating historical sites to explore.

  • Stunning natural beauty: The Greek Islands are renowned for their breathtaking landscapes, featuring crystal-clear turquoise waters, dramatic cliffs, and pristine beaches. Each island has its own unique charm, offering a diverse range of scenery and experiences.

  • Friendly locals: The Greek people are known for their warm hospitality and love of life, making it easy to feel at home in their beautiful country. You’ll find welcoming tavernas, lively festivals, and a strong sense of community on every island.

  • Ease of navigation: The Greek Islands are relatively close together, making it easy to island-hop and explore multiple destinations on a single trip. The prevailing winds are generally predictable, and there are plenty of safe harbors and anchorages to choose from.

Choosing the Right Boat

When it comes to exploring the Greek Islands by sailboat, there are several factors to consider when choosing the right vessel for your journey:

  • Size: The size of your boat will depend on the number of people in your crew and the level of comfort you desire. A 30-40 foot sailboat is suitable for a small family or group of friends, while larger groups may require a 50-60 foot yacht.

  • Type: There are two main types of sailboats to choose from: monohulls and catamarans. Monohulls are more traditional and offer a more authentic sailing experience, while catamarans provide greater stability and more living space. Both types have their pros and cons, so it’s essential to consider your preferences and sailing experience when making a decision.

  • Charter or own: If you don’t already own a sailboat, you can choose to charter one for your Greek Island adventure. There are numerous charter companies operating in Greece, offering a wide range of boats and services. Be sure to research and compare options to find the best fit for your needs and budget.

Best Time to Sail

The sailing season in Greece typically runs from April to October, with the peak months being July and August. However, the best time to sail the Greek Islands depends on your preferences and priorities:

  • Spring (April-May): The weather is mild and pleasant, with fewer tourists and lower prices. The sea may still be a bit chilly for swimming, but the islands are lush and green, with wildflowers in full bloom.

  • Summer (June-August): This is the most popular time to sail, with warm temperatures, steady winds, and plenty of sunshine. The islands are bustling with activity, and the sea is perfect for swimming. However, prices are higher, and popular destinations can be crowded.

  • Autumn (September-October): The weather is still warm and sunny, but the crowds have thinned out, and prices have dropped. The sea remains warm enough for swimming, and the islands are quieter and more relaxed.

Sailing the Greek Islands requires a good understanding of the local weather patterns, tides, and currents. Here are some key factors to consider when planning your route:

  • Meltemi winds: The Meltemi winds are a dominant feature of the Aegean Sea, blowing from the north/northwest during the summer months. These winds can be strong and persistent, making sailing more challenging, especially for inexperienced sailors. Be sure to monitor the weather forecasts and plan your route accordingly.

  • Tides and currents: The tidal range in the Greek Islands is relatively small, but currents can be strong in some areas, particularly around headlands and narrow channels. Be sure to consult local charts and pilot books for information on currents and potential hazards.

  • Harbors and anchorages: The Greek Islands offer a wide range of harbors and anchorages, from bustling marinas to secluded bays. Be sure to research your options in advance and have a backup plan in case your preferred anchorage is full or unsuitable.

Top Greek Island Destinations

With so many islands to choose from, it can be challenging to decide where to go. Here are some of the top Greek Island destinations to consider for your sailing adventure:

  1. Santorini: This iconic island is famous for its stunning sunsets, white-washed villages, and dramatic caldera. Be sure to visit the towns of Fira and Oia, and don’t miss the ancient ruins of Akrotiri.

  2. Mykonos: Known for its vibrant nightlife and beautiful beaches, Mykonos is a popular destination for sailors and tourists alike. Explore the charming town of Mykonos, visit the historic windmills, and enjoy the crystal-clear waters of the surrounding beaches.

  3. Crete: The largest of the Greek Islands, Crete offers a diverse range of experiences, from the ancient ruins of Knossos to the stunning Samaria Gorge. Be sure to sample the local cuisine, which is renowned for its fresh ingredients and bold flavors.

  4. Rhodes: This historic island is home to the UNESCO-listed medieval city of Rhodes, as well as the ancient ruins of Lindos. Enjoy the island’s beautiful beaches, and don’t miss the Valley of the Butterflies, a unique natural phenomenon.

  5. Corfu: Located in the Ionian Sea, Corfu is known for its lush green landscapes, Venetian architecture, and vibrant local culture. Explore the charming old town of Corfu, and be sure to visit the nearby islands of Paxos and Antipaxos.

Sample Itineraries

To help you plan your Greek Island sailing adventure, here are two sample itineraries to consider:

  1. Cyclades Islands (7-10 days): Start in Athens and sail to the islands of Kea, Kythnos, Serifos, Sifnos, Milos, and Folegandros, before returning to Athens. This route offers a mix of popular and lesser-known islands, with plenty of opportunities for swimming, hiking, and exploring local culture.

  2. Ionian Islands (10-14 days): Start in Corfu and sail to the islands of Paxos, Lefkada, Ithaca, Kefalonia, and Zakynthos, before returning to Corfu. This route offers a more relaxed pace, with lush green landscapes, beautiful beaches, and charming villages.

Greek Island Sailing Tips

To ensure a safe and enjoyable sailing experience, keep these tips in mind:

  • Be prepared: Make sure your boat is well-maintained and equipped with all necessary safety gear, including life jackets, flares, and a VHF radio.

  • Stay informed: Monitor the weather forecasts and be prepared to adjust your plans if necessary. Keep an eye out for local hazards, such as rocks, reefs, and strong currents.

  • Respect local customs: The Greek Islands have a strong sense of tradition and community, so be sure to respect local customs and etiquette. Dress modestly when visiting churches and monasteries, and be mindful of noise levels when anchoring near residential areas.

  • Learn some Greek: While many Greeks speak English, learning a few basic phrases can go a long way in making connections with locals and enhancing your overall experience.


Sailing the Greek Islands is a once-in-a-lifetime adventure, offering a unique blend of history, culture, and natural beauty. With careful planning, the right boat, and a spirit of adventure, you can create unforgettable memories and experiences that will last a lifetime. So hoist the sails, chart your course, and set off on your own Greek Island odyssey!