Disclosure: I need to let you know that if you click on some links within the post, I may earn a few pennies. I may have also been compensated to write this article, gifted an item, or been hosted on a press trip. Please see My Travel Monkey's full Disclosure Policy for more details.

Greece is full of wonder – it’s one of the most visited countries in Europe and a staggering 32 million tourists flocked there last year. And the trend is only set to rise. Why? From spectacular coastlines, a number of islands, pretty landscapes and a wealth of ancient history, Greece is the destination to visit.

Sailing Holidays in Greece

There is one way to see the sights away from the crowds and that’s by choosing to travel by sea. Sailing holidays in Greece not only give you the freedom and flexibility of your own yacht or flotilla but the chance to discover hidden coves and gems, which you wouldn’t necessarily know about if you’re confined to land.

Greece actually has 6,000 islands but don’t let that deter you from booking a family sailing holiday – only 62 are densely populated! Covering two main seas, the Aegean and the Ionian Sea, there is much to explore from the water, which gives you a different vantage point, plus you get the privacy of staying on your own boat, able to hop on and hop off when the mood takes your fancy.

The Most Amazing Places To Go Sailing In Greece | My Travel Monkey

The Most Amazing Places To Go Sailing in Greece

You don’t have to know how to sail, these days you can get your own skipper but the great thing about sailing in Greece is the sea is generally calm, there are balanced wind conditions, empty bays, marinas and lovely tavernas to dine in. Meanwhile, it’s easy to travel between one island to another – so covering much of Greece in a short time is feasible. So where to first? Here is the lowdown on the most amazing places to go sailing in Greece.


Surrounded by pine forests, rugged landscapes, olive groves and orchards, Alonissos is in the western part of the Aegean Sea, is relatively untouched in terms of tourism and holds a certain captivating charm. The island is in the remotest part of the Northern Sporades islands, where you can also discover a plethora of wildlife including rare seabirds and monk seals in the National Marine Park. You can easily hop from Alonissos to neighbouring Skiathos, Skopelos and Skyros, and enjoy the buzz of the busier islands.


While most people head to Athens for sightseeing, ancient history and culture, there are in fact has over 21 beaches which can found all along the southern and the northeastern side of the Attica peninsula, which is one of the main departure points to the islands. Head west to Cape  Sounion where you will find pretty sandy coves to swim in, and the famous ancient temple of Poseidon which is perched 60 metres above the sea and is a sight to behold.  Meanwhile, just before Sounion is the secluded Legrena, where you can bathe in crystal clear waters without the crowds.

The Most Amazing Places To Go Sailing In Greece | My Travel Monkey


The largest of the Greek islands, Crete has a wealth of heritage to explore – from archaeological sites such as the Minoan palaces of Knossos to castles such as  Heraklion, as well as the largest gorge in Crete  – Samaria – which affords the most spectacular views. Meanwhile, the breathtaking Balos lagoon is worth a visit, as well as the beautiful beaches of Chania, Rethymno, and Elounda to name but a few. While sailing in Crete, you’ll also get the opportunity to come across lots of hidden coves and hotspots surrounded by azure seas.


The Cyclades is famed for its stunning beaches and picture postcard whitewashed houses with blue windows, windmills and thatched roofs. While the more popular islands of Santorini (see below) and Mykonos attract the crowds, the larger of the islands including Naxos are well worth stopping at. If you’re looking for spots more off the beaten track, then perhaps sail to the smaller islands including Schinoussa which is calm, peaceful and relaxing.  Elsewhere, Agia Anna has an Instagrammable beach – golden sands and turquoise waters. There is a small fishing port and village with numerous seafood restaurants and tavernas. A greats spot for a bite to eat and a swim in the sea.


The Dodecanese are a group of 12 islands and 40 smaller islets and rocks which are situated on the Turkish coast. Kos and Rhodes are probably the most visited Dodecanese islands which are both lively and pretty much sun-drenched the whole year around. Even though Rhodes is popular, there are hidden gems to be found, while a visit to the medieval Old Town is a must and a trip to the village of Lindos where you can see the Acropolis. Meanwhile, for those searching for a little idyll, then it’s the smaller islands that can offer up Byzantine history, Venetian architecture and traditional tavernas.

The Most Amazing Places To Go Sailing In Greece | My Travel Monkey

Ionian Islands

During our trip to Zakynthos last summer, it was the Ionian sea that made me never want to leave. So blue and so calm, I spent all my time mesmerised by it. During the season, those lucky enough will be able to see loggerhead turtles – as well as the famous shipwreck on Navigio Beach and the Blue Caves. Other popular destinations in the Ionian are Lefkada, Kefalonia (another one of my favourites) and Corfu, which all have an abundance of secluded coves and beaches.


Arguably the most visited of all the islands in Greece, Santorini’s world-famous white buildings and blue domes are recognisable anywhere. A sailing holiday in Greece wouldn’t be complete without taking in these magnificent views of Oia from the sea. The added bonus of being on the deck of a private sailing yacht is that you can find hidden gems only accessible by boat – as well as explore the volcano and the hot springs – a water-filled caldera without leaving the deck. Meanwhile, instead of jostling with the crowds, you can also enjoy the awe-inspiring Santorini sunsets in the comfort of your yacht.

The Most Amazing Places To Go Sailing In Greece | My Travel Monkey


Not only has the tranquil island of Thassos littered with over 30 spectacular beaches including Alyki and Paradise Beach – which are perfect for families, but it has rugged and lush terrain. For those in love with nature,  the small island of Panagia is a  protected marine ecosystem part of the 2000 Natura network along the southern coast, and if you’re lucky enough, you may even see a pod of dolphins.  Meanwhile, Thassos offers hikers and walkers many trails cross the countryside passing through mountainous villages and gorges including the spectacular rock formations of Giola – which has a small lagoon inside rocky seaside cliffs.

Disclosure: This post may contain compensated links.*