Sailing holidays in Greece with a local skipper
The Greek Archipelago has over 16,000 km of coastline, with many beaches that run for kilometres, a host of secluded bays and coves, and a rich variety of wildlife. Some say the best sailing waters in the world can be found in Greece!
If you find the same experience for a lower price elsewhere, we’ll match the price.
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!
Customer Support
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!6 reasons to explore Greece on a catamaran for your next sailing holiday:
- Discover some of the world’s most beautiful coves and lagoons in the comfort of a catamaran.
- Explore the thousands of Greek islands aboard a catamaran with a weak draft, allowing them to venture into shallower waters than a monohull - meaning you can travel with an unrivalled level of freedom!
- Board a spacious catamaran, that allows a most comfortable sailing experience possible - especially when travelling as a family or a larger group!
- As a catamaran has less movement at sea than a monohull sailboat, it is perfect for first time sailors, reducing any concerns about sea sickness.
- Experience all of the treasures of Greece - including the famous isles of Santorini, Mykonos, and Ios as well as the native sirtaki dance of the street festivals.
- Immerse yourself into the beautiful atmosphere and charming architecture of Greece’s coastal regions aboard a catamaran.
The best destinations to visit on your holiday to Greece aboard a catamaran:
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. Corfu, Mykonos, and Santorini are some specific destinations that are particularly magical to explore by a sailing holiday.
Travelling the Greek isles by sailboat allows for full exploration of the areas treasures, that would otherwise be inaccessible. This is even more so the case when travelling by catamaran, due to the weak draft of the boat, meaning shallow waters inaccessible to many monohull boats can be explored! 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. Learn more about sailing in Greece.
Tips to help you to better plan for your next sailing holidays in Greece aboard a catamaran:
When to visit Greece & transport options
Temperatures and the climate in Greece are pleasant and generally good for sailing from April through to November. Due to the fact that July and August are more popular for holidaying, if possible, it is worth considering travelling during May, June, September, or October if you would prefer a quieter, slightly more tranquil holiday.
Greece is home to a number of international airports such as Athens, Corfu, Kos, and Kefalonia. Greece has a well developed system of ferries that transport travellers from island to island. The organising skipper of any given trip will be able to give you the most relevant information about transport routes to and from your points of embarkment and disembarkment.
Sailing with a family aboard a catamaran with a local skipper
There are some sailing regions that are better suited and equipped for family sailing trips, and Greece is one of these regions. There is a good mix of modern marinas and harbouring options as well as more secluded bays and coves for you to enjoy with your family. All forms of sailing holiday with family holidays included, benefit greatly from having an experience local skipper leading the trip. Travelling with a skipper with such insider knowledge allows you to fully immerse yourself in the enjoyment, relaxation, and adventure of the sailing holiday in the Greek isles.