Greece is a country with an extensive coastline, the Greek archipelago is made up of thousands of islands with over 200 that are inhabited, all spread over the Aegean, Ionian and Mediterranean seas. Naturally this has led to Greece becoming a global hub for sailing holidays. 

A sailing holiday is amazing and probably the best way of exploring the Greek islands. There is a unique sense of freedom, you can plan your routes as you wish and stop when you want. 

Skippered, Bareboat or Flotilla

When planning a sailing trip, you’ll be presented with 3 main options a skippered boat, a bareboat or Flotilla. A skippered boat is one that you rent that comes with either a captain or a captain and a whole crew that may include a chef, butler and organiser. A bareboat trip on the other hand is when you only rent the boat and sail independently. A flotilla is almost in the middle of the two, it’s when you rent a boat to sail yourself but in the company of other boats all led by an experienced lead crew.

A skippered sailing trip is perfect if you wish to travel alone without the pressures of running a vessel yourself. You can set your own course and liaise with a captain on what you’d like to do. Captains are multi-lingual and can organise water sport activities, things to do on the islands and meals. On average skippers cost about an extra 1000 euros per week.

A bareboat trip does offer the same benefits as a skippered one except you will be in complete control. Sailing experience and licences are necessary and it helps to have some prior knowledge of the local islands and key spots. This trip is the most discreet and offers complete and utter freedom on the seas.

Flotilla holidays offer a more sociable approach and an opportunity to enjoy a more communal Greek island experience. Flotillas can be specialised into food and wine flotillas or adults only flotillas.  Flotillas offer a great opportunity to learn how to sail while in the company of an experience lead crew. If that’s not your thing you can even hire a skipper for the duration of your trip. These trips however are on a set course so don’t offer the flexibility and freedom of bareboat and skippered trips.

The Right Vessel

There are several types of vessels for you to think about when planning your trip. The advantages of each depend on how many people in your party, free time and the distance that needs to be covered. 

Monohull and catamarans sailboats are great for a classic sailing experience. Catamarans are bigger than monohull boats, but both are ideal for small groups and those interested in spending time in the sea.

A motorboat on the other hand is better for covering the largest distance in the shortest time, and perfect for those not interested in sailing as a sport. Motorboats tend to be more relaxing and offer more time onboard the boat to relax, as opposed to sail. A luxury yacht offers all the same benefits of a motorboat but with much more in the way of space, amenities, décor, crew and activities. These vessels are suited to big groups with large budgets. 

If you want much more space and are traveling in a large group than a gulet may be for you. A gulet is a traditional wooden sailing boat that’s much bigger than a monohull or catamaran vessel. Gulets are spacious and have huge open decks but require a full crew. With a gulet you will still be able to enjoy sailing as a sport but will need help as it’s such big vessel to man alone.