Why you should book a holiday with Sailsquare?
The leading sailing holiday marketplace
25,000+ happy travellers, and 10,000+ holidays in 110 destinations worldwide.
Get onboard solo, with your family, or your friends
Reserve a single spot, a cabin, or a whole boat just for you and your friends or family.
Discover who’s already onboard
Introduce yourselves online, get to know each other onboard, and go home with a bunch of new friends.
Sailing holidays that suit all budgets
Rumour has it that sailing holidays are only for the rich or well-connected. With Sailsquare, that's no longer true. Come and discover a world you never thought was accessible!
Reviews - Sailing holidays in Greece with a local skipper1083 reviews
Would you like some support using the platform? We've (almost) always got the answers!
Can't find the perfect holiday for you?
Use our free holiday concierge tool - and let us find your dream sailing experience for you!Let's find it together!
8 reasons to choose Greece for your next sailing holidays:
- Excellent sailing conditions throughout the year, with calmer areas and areas for more advanced sailing
- Thousands of unique islands to explore, including some of the world’s most beautiful
- Delicious local specialties, such as: tzatziki, tarama, moussaka, dolmades, the famous Gyros, and of some of the traditional Greek liquor Ouzo and Raki
- Home to some of the most spectacular beauty in the Greek Isles in Santorini, Mykonos, and Ios
- Endless sailing itineraries to be designed with your skipper
- Immerse yourself in the regions iconic white, cubic architecture and charming fishing villages
- Discover some of the world’s most charming coves and lagoons
- Learn the special sirtaki dance in the area’s street festivals
The best places & specific destinations to visit during your sailing holiday in Greece:
Famous sailing areas include the Cyclades, the Saronic islands, Ionian islands, Dodecanese, Sporades, and Crete - however, there are an estimated 5,000-6,000 islands in Greece. Travelling the Greek isles by sailboat allows for full exploration of the areas treasures, that would otherwise be inaccessible. Whether you are planning to travel solo, as a couple, with friends or family, and whether you are looking for a sailboat or catamaran experience, there are numerous areas of Greece that make for perfect holidaying destinations.
The variety of sailing in Corfu between coastal town hopping and more open water routes, make it a great destination to gather a well-rounded sailing experience. Surrounding Corfu are some smaller Ionian Islands, with striking beauty and unique wildlife ecosystems - along with the coast of Albania to the north, there is much surrounding the region to explore.
The area is named after the grandson of Greek god Apollo - god of music, art, and the sun - Mykonos is often described as the heart of the Cyclades, and an excellent place to observe some of the richest history and tradition in Greece. Alefkántra or 'Little Venice' in Mykonos' capital town Hóra, is a beautiful example of such history - the 18th district of the town is recognised for its unique architecture, and its relationship with the sea it is perched above.
As a precious jewel of the Aegean, and a place of striking natural beauty, Santorini has become one of the most sort after destinations in Greece. The island is the byproduct of a volcano eruption, which explains the incredibly dramatic views over Oia town, which at sunset is a truly iconic sight to behold. With a collection of golden and red beaches, and natural springs surround the island, exploring the area by island is the only way to truly experience it.
Tips to help you to better plan for your next sailing holidays in Greece:
All you need to know about your next cruise in Greece aboard a sailboat.
When to go to Greece for a sailing holiday
Greece has a pleasant Mediterranean climate throughout the year. The temperatures become particularly pleasant from April until the end of November. The periods of July and August are relatively busy, and travellers may find that in May, June, September and October trip are particularly enjoyable for boarding a sailing or catamaran holiday. The wind is moderate, therefore, you can calmly enjoy the beauty of the islands. If you decide to travel at a busier time of the year, your localised skipper will be able to take you to places tucked away from the masses.
How long should a sailing holiday in Greece be?
The Greek archipelago is vast and it is important to choose the destination according to the available amount of time, so you can fully enjoy the experience without hurry. We recommend a minimum of two weeks to discover the Cyclades and the Dodecanese. If you have less time, we recommend looking at holidays in the Ionian, Saronic, Sporades and Crete.
Transport options to and from your holiday
Greece has many international airports including Athens, Corfu, Kos, and Kefalonia where there are budget airline options. Prices can increase significantly during school holiday periods, mainly summer in July and August. We would recommend going slightly outside of the main season in May, June, September, and October. Greece has a highly developed ferry network that connects the main islands with each other, it might be required that you use one of these ferry routes in order to reach your skipper. Your skipper will be able to advise you on the best flights and additional ferry services that might be necessary.
Sailing holidays in Greece with a family
There are some sailing destinations that are particularly suitable for family holidaying. Greece is one of these destinations. The sailing conditions are ideal and the mooring opportunities are numerous. You will easily find a deserted cove where you can find an anchor spot for the kids to have fun on the beach or shallow waters. Sailing holidays are fun for both young and old!
Sailing holidays in Greece - why you should travel with a local skipper
If you want to fully enjoy your sailing holiday in Greece in the best conditions, we recommend that you go choose a trip with a local skipper. Travelling with a skipper who has insider knowledge on the area, allows travellers to fully immerse in the pleasure and relaxation of the holiday. Where individuals on the trip wish to learn or practice their sailing skills, skippers will be there to integrate travellers into the responsibilities onboard.
The best sailing itineraries for your next holiday with a skipper in Greece
- The big Cycladic Tour: For this trip two weeks are needed to explore this archipelago from Athens. The first part of the trip will be to explore the islands of the small Cyclades ( Kea, Siros, Tinos, and Kithnos), before heading to the archipelago of the great Cyclades (Naxos, Milos, Ios, Sifnos, and Amorgos) where there is the option to push up to Santorini. The return can be made directly to the port of Piraeus in Athens, or by first making a detour to the Saronic Islands (such as Hydra).
- Cruise around the minor Cyclades: a very beautiful adventure, and ideal for a week or more away from the powerful Meltem that can blow during the summer months in the great Cyclades. From Athens, you could then consider exploring the beautiful Kea, Siros, Tinos, Kythnos and Serifos.
- Discover the Ionian Islands and the Sea of Ulysses: a wild and untouched archipelago that is ideal for a week of relaxation. Fiscardo, the white cliffs northwest of Ithaca, the beautiful village of Kioni and its beautiful bay, the isolated island of Atokos without forgetting to stop by Kalamos and Kastos. Lefkada is then not too far away with a final well-deserved stopover before arriving to the charming port of Sami in Kefalonia.
- The beautiful islands of northern Corfu: get ready for an extraordinary adventure exploring the islands of Mathraki, Erikoussa and Othonoi. Deserted beaches, very few inhabited islands, splendid moorings - a destination perfect for a holiday made of serenity.
- The magical journey to Saronic Islands sailing from Athens: a splendid region sheltered from the wind and waves for calm and pleasant island hopping. From Athens, the first step can be Hydra (famously, the island without a car). After a hike ini Leonidio, you can then reach the islands of Dokos for a BBQ on the beach at Poros, and end the voyage with a cultural stopover in Epidaurus.
- Exploration of the Sporades: with a week at sea aboard a sailboat, you are sure to uncover some of the wonders of the Sporades. Let yourself be carried by the wind to the islands of Skiathos, Skopelos, Alonissos, Kyra Panagia, and Peristera.
- Discovering the Dodecanese: From the island of Rhodes (the largest of the archipelago), embark on a wild sailing holiday with changing sceneries. On the agenda: hopping along the Turkish coast to reach the ruins of Bouzoukale and the charming village of Bosborum, visiting the island of Symi, the Datca Peninsula and the small port of Palamut. Finally, the island of Nisyros and its volcano make for an excellent last stop before heading back to Rhodes.