Complete Guide to Sailing the Greek Islands
Written by  Daisie Team
Published on 9 min read


  1. Prepare for the journey
  2. Visit the Cyclades Islands
  3. Explore the Saronic Islands
  4. Navigate the Ionian Islands
  5. Discover the Dodecanese Islands
  6. Experience the Northeast Aegean Islands
  7. Travel to the Sporades Islands
  8. Sail around the Crete Island
  9. How to handle the boat
  10. What to carry along

Imagine feeling the warm Mediterranean sun on your skin, the cool breeze tugging at your hair, and the gentle lapping of waves against the hull of your boat. This is what awaits you when sailing in the Greek Islands. With a rich history, stunning landscapes, and tranquil blue waters, Greece offers a unique sailing experience for both beginners and seasoned sailors. This blog will serve as your compass, guiding you through everything you need to know about sailing in the Greek Islands.

Prepare for the Journey

Before you set sail on the adventure of a lifetime, you need to prepare. Good preparation can be the difference between an enjoyable trip and a stressful one. Here are some things you should consider:

  • Weather: Greece has a Mediterranean climate. This means warm, dry summers and mild, wet winters. The sailing season usually starts in April and ends in October. However, the best time for sailing in the Greek islands is considered to be from May to September when the weather is most favorable.
  • Sailing Skills: Confidence in your ability to handle a boat is important. If you're a newbie, consider taking a few sailing lessons before your trip. This will help you understand the basics of sailing and navigation. You don't need to be an expert, but knowing the ropes will definitely enhance your sailing experience.
  • Route Planning: The Greek Islands are divided into several groups - the Cyclades, the Saronic, the Ionian, the Dodecanese, the Northeast Aegean, the Sporades, and Crete. Each group has its own charm and attractions. Plan your route based on what you want to see and do. Remember, the journey is just as important as the destination!
  • Boat Selection: The type of boat you choose will depend on your budget, the size of your crew, and your sailing skills. Options range from small sailing yachts perfect for couples or small groups, to larger catamarans or motor yachts ideal for larger parties. Make sure to choose a boat that fits your comfort and needs.

Preparing for your sailing trip to the Greek Islands may seem like a lot of work, but trust me, it's worth it. Once you're out there on the sparkling blue waters, with the wind in your sails and the sun on your face, you'll be glad you took the time to prepare.

Visit the Cyclades Islands

Let's start our sailing journey in the Greek Islands with the Cyclades. This group of islands is the most popular among sailors—and for good reason. With their white-washed houses, blue-domed churches, and windmills, the Cyclades are the picture of idyllic Greek beauty.

  • Mykonos: Known for its vibrant nightlife and beautiful beaches, Mykonos is a must-visit when sailing in the Greek Islands. By day, explore the narrow, winding streets of Mykonos town. By night, enjoy the lively beach bars and clubs that make this island famous.
  • Santorini: No trip to the Cyclades would be complete without a stop at Santorini. With its stunning sunsets, unique architecture, and world-class wineries, Santorini is a truly unforgettable destination.
  • Paros: This island is a sailor's dream, offering safe harbors and plenty of anchorages. Paros is also known for its gorgeous sandy beaches and charming villages.

If you're looking for a blend of cultural experiences, beautiful landscapes, and a taste of the high life, the Cyclades Islands are just the ticket. Each island has its own story to tell, making your journey of sailing in the Greek islands a truly unique experience.

Explore the Saronic Islands

Next on our sailing adventure around the Greek islands, we arrive at the Saronic islands. These islands are a stone's throw from Athens, making them an easy and convenient option for sailors. But don't let their proximity fool you, these islands boast stunning natural beauty and rich history.

  • Aegina: Aegina is famous for the Temple of Aphaia, a well-preserved ancient Greek sanctuary. This island also offers bustling markets, a lively port, and delicious pistachios — they're a must-try when you visit!
  • Hydra: One of the most unique features of Hydra is the absence of cars. Donkeys are the main mode of transportation here, adding to the island's charm. Hydra is also home to an engaging maritime museum and stunning mansions that date back to the 18th century.
  • Poros: Poros is a small island, but it packs a punch with its lush pine forests and beautiful sandy beaches. A visit to the Historical and Folklore Museum will give you a glimpse into the island's past.

With their rich cultural heritage and stunning landscapes, the Saronic Islands are an excellent choice when sailing in the Greek islands. They offer a perfect blend of relaxation and exploration for an unforgettable sailing experience.

The next stop on our Greek sailing adventure is the Ionian Islands. Known for their breathtaking beaches, lush vegetation, and unique architectural style, these islands will surely leave you in awe. So, let's dive into what each island has to offer:

  • Corfu: Corfu is a melting pot of cultural influences, with Venetian, French, and British elements visible in its architecture. Make sure to visit the Old Fortress and stroll around the charming Old Town.
  • Kefalonia: Famous for its stunning beaches and turquoise waters, Kefalonia is a paradise for nature lovers. Don't miss the mesmerizing Melissani Cave and the majestic Mount Ainos.
  • Zakynthos: Home to the iconic Shipwreck Beach, Zakynthos is a must-visit. While here, take a chance to explore the beautiful Blue Caves and the endangered sea turtle nesting site at Gerakas Beach.

When sailing in the Greek islands, the Ionian Islands are certainly a destination to mark on your map. Their unique charm, combined with their natural beauty, makes for a memorable part of your Greek island sailing journey.

Discover the Dodecanese Islands

As we continue sailing in the Greek islands, we journey east to the Dodecanese Islands. This group of 12 larger plus 150 smaller islands is steeped in history and natural beauty, with each island offering its own unique experience.

  • Rhodes: Rhodes, the largest of the Dodecanese Islands, is known for its beach resorts, ancient ruins, and remnants of its Crusader past. Highlights include the Medieval City of Rhodes, a UNESCO World Heritage Site, and the ancient city of Kamiros.
  • Kos: With long sandy beaches and a vibrant nightlife, Kos is a popular spot for tourists. But it's not just about the beaches. You'll find ancient Greek and Roman landmarks, including the Asklepieion, one of the most significant archaeological sites in Greece.
  • Patmos: Known as the 'Jerusalem of the Aegean', Patmos is a place of pilgrimage due to its connection to Saint John the Divine. The Monastery of Saint John the Theologian and the Cave of the Apocalypse are must-visits.

From historical sites to stunning coastlines, the Dodecanese Islands add a unique flavor to your journey while sailing in the Greek islands. Don't forget to try out the local cuisine, as each island has its own delicious specialties!

Experience the Northeast Aegean Islands

Now, let's set the sails a bit more north and explore the Northeast Aegean Islands. They might be less famous than their southern siblings, but trust me, they are just as stunning and offer a more relaxing, authentic Greek experience.

  • Lesbos: Lesbos, also known as Mytilene, is famous for its olive oil, ouzo, and beautiful petrified forest. Don't miss the picturesque villages of Molyvos and Plomari, and try the local sardines - they're a delicacy here.
  • Chios: Famous for its mastic trees and medieval villages, Chios is truly unique. Pay a visit to the Mastic Museum and the village of Pyrgi, known for its black and white geometrical patterns on houses.
  • Samos: Samos is the birthplace of the famous mathematician Pythagoras. But that's not all - its white sandy beaches, lush green mountains, and sweet Muscat wine will make you fall in love with this island.

These islands are a bit off the beaten track, making them perfect for those who want to experience the real Greece while sailing in the Greek islands. With their rich history, unique local products, and stunning landscapes, the Northeast Aegean Islands are well worth a visit.

Travel to the Sporades Islands

Next on our Greek sailing adventure, let's catch the wind to the Sporades Islands. Known for their stunning natural beauty and crystal clear waters, these islands will leave you speechless.

  • Skiathos: Skiathos may be small in size, but it's big in charm. With over 60 beaches to explore, you'll never run out of stunning spots to anchor your boat. And don't forget to visit the old town with its traditional houses and narrow streets.
  • Skopelos: Remember the movie "Mamma Mia"? It was filmed right here on Skopelos. Aside from its Hollywood fame, Skopelos is known for its lush greenery, beautiful churches, and delicious local cheese.
  • Alonnisos: If you're a nature lover, Alonnisos will be your paradise. Home to the National Marine Park of Alonnisos, this island is a haven for rare seabirds, dolphins, and the endangered Mediterranean monk seal.

A trip to the Sporades Islands will add a dose of nature, beauty, and tranquility to your journey sailing in the Greek islands. The blend of turquoise waters, green landscapes, and charming villages is something you won't easily forget.

Sail around the Crete Island

Now, let's set sail for the largest of the Greek islands — Crete. Known for its diverse landscapes and rich history, Crete is a must-visit when sailing in the Greek islands. It's like a country within a country, offering everything from snow-capped mountains to sun-kissed beaches.

  • Heraklion: Start your journey in the vibrant city of Heraklion. Pay a visit to the ancient Palace of Knossos, considered Europe's oldest city, and the Heraklion Archaeological Museum, housing treasures from Crete's long history.
  • Chania: Sail west to Chania, a city where the past and present coexist. Walk along the old Venetian harbor, take in the charming old town, and try some of the island's best seafood.
  • Elafonisi: A little further west, you'll find the exotic beach of Elafonisi, known for its pink sand. Yes, pink! It's an ideal spot to anchor your boat and spend a leisurely day soaking up the sun.

Crete is a treasure chest of experiences waiting to be opened. It's not just about the destination, but the journey of sailing around it that makes it one of the most rewarding parts of sailing in the Greek islands.

How to handle the boat

Now that we've talked about where to go, let's discuss something equally important: how to handle the boat. Don't worry if you're not a seasoned sailor — with some basic knowledge and practice, you'll soon feel confident steering your own vessel while sailing in the Greek islands.

  1. Get to know your boat: Familiarize yourself with the parts of the boat and their functions. Understand what the rudder, sail, and hull do. Remember, knowing your boat is the first step to controlling it.
  2. Master the basics: Learn how to steer, adjust the sails, and anchor. These are basic skills that every sailor should know. Practice makes perfect, so don't rush.
  3. Understand the wind: The wind is your friend when you're sailing. Learn how to read its direction and adjust your sails accordingly. Remember, you can't control the wind, but you can adjust your sails.
  4. Stay safe: Safety should be your top priority. Always wear a life jacket, keep a close eye on the weather, and have a plan in case of emergencies.

Handling a boat can seem daunting at first, but with time and practice, you'll be sailing like a pro. It's all part of the adventure of sailing in the Greek islands. So, are you ready to take the helm?

What to carry along

When you're getting ready for your sailing trip in the Greek islands, packing can be a bit of a puzzle. But don't worry, we've got you covered. Here's a simple list of things you should definitely have with you:

  1. Sunscreen: The Greek sun can be intense, especially in the summer. So, a good sunscreen is a must-have to protect your skin.
  2. Comfortable clothes: Pack light, breathable clothes. Don't forget your swimsuit, a hat, and a light jacket for cooler nights.
  3. Waterproof bag: A waterproof bag is handy for keeping your belongings dry, especially when you're on the boat.
  4. Snacks and water: You'll need plenty of water to stay hydrated. Also, pack some snacks for when hunger strikes in between island stops.
  5. First aid kit: It's always a good idea to have a basic first aid kit on board. It should include band-aids, antiseptic wipes, and motion sickness tablets.
  6. Camera: You'll definitely want to capture the breathtaking views and memorable moments. So don't forget your camera!

Packing right can make a big difference in your sailing experience. So, take your time, check your list, and get ready to set sail. Remember, the Greek islands are waiting for you!

If you found this blog post on sailing the Greek Islands inspiring and want to capture the breathtaking landscapes you'll encounter on your journey, check out Sofia Podestà's workshop, 'Find Your Way in Landscape Photography.' This workshop will help you develop your photography skills, allowing you to capture the beauty and essence of the Greek Islands.