Mediterranean
The 15 Best Greek Islands for Sailors in 2026
With over 6,000 islands and islets scattered across Greece, and each one offering something unique, it can feel overwhelming trying to decide where to explore on a sailing holiday, particularly if you’re a first-time sailor.
To help simplify planning your first yacht charter, we have created a Greek island travel index to unveil the top 15 must-visit Greek hotspots for beginner sailors, chosen for their easy sailing grounds and genuine local charm.
From car-free havens to undiscovered islands with beaches only accessible by boat, the list showcases the very best of Greece’s lesser-known landscapes, beaches, architecture, and culture, for first-time sailors to discover away from the crowds.
How did we Curate our Greek Island Travel Index?
We have used a range of online search data, TripAdvisor reviews, information from official tourism boards, and geological data to rank islands based on the following factors:
- Popularity – The less exposure on social media, but the higher the volume of online searches related to sailing, the more ideal the island is for first-timers.
- Sailing Grounds – How easy, smooth, and safe the sailing grounds are, ensuring a stress-free adventure where you can build your confidence and truly enjoy the view.
- Moorings Options – Islands that offer plenty of mooring options, giving you the choice between the lively, bustling energy of a marina or the quiet uncrowded calm of an anchorage for a peaceful night under the stars.
- Activities – If this is your first time sailing around Greece, you’ll want to experience it in all its glory, so the more diverse the activities, the more opportunities you have to discover the side of Greece that’s only accessible to sailors.
- Beaches – Are local beaches clean, safe, and uncrowded? We have also prioritised beaches based on whether they’re only accessible by boat or not, ensuring you have a slice of Greek paradise all to yourself.
Based on these factors, each island has been given a score out of 26 – the higher the score, the more ideal the island is for first-time sailors.
Any island that received the same score as another has then been ranked according to its population size. The smaller and more secluded the island, the higher the position awarded.
The 15 Best Greek Islands for Sailors
1. Lefkada
Offering stunning natural beauty, authentic Greek culture, and incredible beaches without the overwhelming crowds of more famous Islands, Lefkada has officially been named the must-visit Greek island for first-time sailors in 2026, scoring 24 out of 26.
Lefkada is home to many breathtaking beaches, several of which have been awarded the coveted Blue Flag status for their water quality, safety, environmental education, and cleanliness standards. One of the best beaches in Greece is Egremni Beach, which is only accessible by boat and described by travellers on Tripadvisor as “one of the most beautiful beaches ever seen”.
If you want the full Greek island hopping experience, Lefkada is a paradise, as there are so many small islands within a short distance that you can discover, such as Kastos. Home to fewer than 100 permanent residents, Kastos feels like a floating village. With only one small harbour, a cluster of stone houses, and a few tavernas, time seems to slow down here.
Want to discover the treasures of Lefkada, Kastos, and other nearby islands for yourself? Set sail on an idyllic yacht charter with Sunsail and explore the wonders of the Ionian Sea, casting off from our base in Lefkada. Build a quote and start planning your Lefkada sailing itinerary today.
2. Meganisi
With less than 1,800 videos on TikTok using the hashtag #Meganisi, and a population of around 1,200 people, Meganisi is one of the most underrated Greek islands of 2026, scoring 22 out of 26.
It has a laid-back, authentic Greek vibe with fishing villages, traditional family-run tavernas, and underground caves to explore, and is one of the few Ionian islands that remain untouched by mass tourism.
Meganisi is also home to Papanikolis cave, one of the largest and most famous sea caves in Greece, and once used as a hideout by submarines during WWII. One TripAdvisor review says: “What an amazing place. A huge sea cave with a beach inside. Beautiful, clear blue water […] Great story about the Greek submarine hiding there during WW2, you can just imagine it.”
If you’re a beginner sailor looking to enjoy a sociable charter surrounded by other sailors, book an idyllic Meganisi flotilla with Sunsail.
3. Ithaca
Rounding up the top three on our list of the top 15 Greek islands for first-time sailors is Ithaca, scoring 22 out of 26.
A peaceful, quiet, and undiscovered island, Ithaca is steeped in historical and mythological significance, and renowned for being the home of Odysseus.
With stunning Blue Flag beaches, short sailing distances, calm waters, and a tranquil atmosphere, Ithaca is a dream for beginner sailors. To really make the most of your Greek island experience, don’t forget to head to Kioni and taste Ithaca’s local delicacy, Onion Pie.
You can step straight into the pages of Homer’s The Odyssey by following one of our carefully-curated Lefkada sailing itineraries.
4. Hydra
With exceptionally preserved 18th-century stone architecture and stunning pebble coves, Hydra is one of the most serene, picturesque Greek islands, scoring 21 out of 26.
With no cars or bicycles and only donkeys for transport, Hydra feels like a step back in time, introducing you to a truly slower pace of life.
If you want to experience true peace and quiet while sailing around Hydra, anchor at one of the tiny, uninhabited Kelevini Islands for a chilled-out lunch break miles from the nearest town.
Love the sound of switching off on the stunning island of Hydra? Discover our Athens sailing itineraries, which take you around Hydra, Aegina, Spetses, and other beautiful Saronic Islands. Build a quote and book your Athens yacht charter today.
5. Spetses
Want to continue your Greek island-hopping adventure around the sensational Saronic islands?
Another island where private cars are banned, the gorgeous island of Spetses is renowned for its aristocratic flair, neoclassical mansions, and rich nautical history, scoring an impressive 21 out of 26.
Spetses has a relaxed but elegant atmosphere, making it a perfect blend of history and natural beauty, ideal for your first yacht charter in Greece.
Uncover the hidden world of Spetses by following one of our Athens sailing itineraries.
6. Aegina
Next on our list of the best Greek islands for first-time sailors is Aegina, offering short sailing distances, mild winds, several mooring options across the island, and scoring 21 out of 26.
For mythology lovers, Aegina is the place to visit, as, according to Greek mythology, Zeus fell in love with the prettiest daughter of God Aesopus, Aegina. He kidnapped Aegina and brought her to the island Inoni, which was later named Aegina.
When you moor up and explore Aegina on your Athens yacht charter, don’t forget to take a ride in the traditional carriages, taste the famous local pistachios of Aegina, and have lunch at the traditional taverns with fresh fish accompanied by ouzo.
7. Kefalonia
Scoring a fantastic 21 out of 26, Kefalonia is a sensational Greek sailing hotspot loved by beginner and experienced sailors alike.
One of the must-visit spots on Kefalonia is Agia Eufemia, a charming coastal village that beckons sailors with its picturesque beauty and inviting waters. The prevailing winds in the region are typically light to moderate, making for pleasant sailing conditions for beginner sailors.
Want to channel your inner adventurer? There’s still plenty to be explored here, as there are two sets of caves, the Drogarti inland and the Melisani caves, which you can be taken in by a boatman. Many describe this as entering Hades itself. The water is dark and inky with turquoise patches where the sun hits, and the caves are linked to the Melisani Lake further inland by underwater passages.
Discover the wonders of Kefalonia and the surrounding islands on our fun-filled Kefalonia flotilla, loved by first-time sailors, families, couples, and everyone in between.
8. Corfu
From switching off and unwinding on unspoiled Blue Flag beaches, such as Glyfada Beach, to immersing yourself in the vibrant local culture, and going snorkelling or scuba diving in crystal-clear waters, there’s something for everyone on a sailing charter around magical Corfu, which is why it’s scored 21 out of 26.
One of the greenest islands in the Mediterranean, Corfu’s lush landscape is idyllic for nature lovers. It’s also steeped in history, with Old Town Corfu being a UNESCO World Heritage Site.
A mixture of sheltered coastal spots and more adventurous blue water stretches makes Corfu an ideal destination to charter a yacht.
Let Sunsail’s 50 years of experience guide you around the famous Heptanese Islands, known for their relaxed culture, beautiful scenery, excellent beaches, and warm, clear waters. Whether you want to take the helm on a bareboat charter or hire a skipper, build a quote and book your Corfu yacht charter today.
9. Sifnos
With an amazing score of 20 out of 26, and a population of less than 3,000 people, the ninth best Greek island for first-time sailors is Sifnos.
Sifnos is renowned for its culinary traditions and is widely renowned as the epicentre of Greek cuisine. The island pays homage to simpler times with its legendary local dishes and traditional clay pots, so you can enjoy an authentic culinary experience.
Will you tuck into Mastelo (lamb or goat baked on a bed of vine branches), Revithokeftedes (crispy, chickpea meatballs), or Manoura cheese (a delicious, spicy cheese)?
10. Skopelos
Do you want to step straight into a film set? Scoring 20 out of 26, Skopelos was the filming location for several iconic scenes in Mamma Mia, including the iconic wedding scene, which took place at the tiny Chapel of Agios Ioannis.
It’s also home to Adrina Beach, a gorgeous cove which has been awarded Blue Flag status. According to one Tripadvisor review, “for those who enjoy adventure, there are stunning rocks with crystal-clear water nearby”, while another said, “there are loads of sunbeds, a little jetty to dive off, and an excellent beach bar/restaurant”.
11. Milos
It’s no surprise that Milos has made our list of the best Greek islands for first-time sailors, scoring 20 out of 26.
An unspoiled paradise, Milos offers dramatic volcanic scenery, gorgeous turquoise waters, and sea caves just waiting to be explored. For any budding art historians, Milos is the original homeland of the world-famous Venus de Milo statue, which is currently located in the Louvre Museum in Paris.
12. Paxos
With just 1,000 TikTok videos using the hashtag #Paxos, and a population of just 2,500 people, Paxos is a true underrated Greek gem, scoring 19 out of 26.
One of the least commercial Greek Islands set in the Ionian Sea, this island is truly beautiful, with scenery that makes it an artist’s paradise. Its clear aquamarine sea and pebble beaches must be seen to be believed. The local people are so welcoming that you feel at home straight away!
It’s a perfect place to wind down; nothing is done quickly here. Sit and drink an iced coffee in one of the seafront cafes, watch a local fisherman bring his catch in to sell, or queue in the local bakery for your fresh bread baked in a wood oven. This is the beauty of Paxos.
Relax and embrace the stillness of Paxos when you follow one of our Corfu sailing itineraries.
13. Skiathos
If you’re looking for unbelievably breathtaking beaches to soak up the sun at during your Greek sailing holiday, look no further than Skiathos, which has scored an impressive 19 out of 26.
Out of the 11 beaches in the Sporades to be awarded Blue Flag status, 10 can be found on this wonderful island. One of which is Koukounaries Beach, with one Tripadvisor review saying: “Fabulous beach and the most beautiful sea to swim in….the sand sparkles gold and fish swim past you. Lovely simple beach bars with fair prices and no WiFi…a good thing in my opinion as you can fully switch off. Lovely walks and well appointed with toilets and changing facilities”.
14. Paros
In the heart of the Aegean Sea is Paros, which combines traditional elements such as architecture, quaint villages, and historical monuments with the lively nightlife and bustling beaches. Offering the best of both worlds, Paros has scored 17 out of 26.
Paros stretches across 120km of coastline and has endless blonde-sand beaches at the bottom of lush mountains, perfect for kitesurfing and windsurfing. If you want a particularly active holiday, explore Paros Environmental and Cultural Park, which has around 80 hectares of walking trails, remarkable rock formations, caves, and hidden coves.
Discover the beauty of Paros on a 14-day Athens sailing charter around the stunning Cyclades.
15. Symi
Taking the last spot on our list of the top 15 Greek islands for first-time sailors is Symi, scoring 21 out of 28.
Symi is renowned for its quaint, neoclassical architecture, so everywhere you turn, you’ll be met by two and three-storey traditional stone houses, painted in lots of different colours. Mooring up and wandering around the picturesque houses is an experience you’ll never forget.
With calm bays and sheltered anchorages, Symi is an excellent destination for first-time sailors, particularly in the spring or autumn, as you’ll avoid the Meltemi winds.
Whether you have already booked your idyllic Greek getaway or are still looking for inspiration on where to set sail from, we hope our list of the best Greek islands for first-time sailors helps you plan your perfect first yacht charter in the stunning Mediterranean.
Discover our Greece yacht charter bases and build a quote today.
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