• Attractions
  • Auctions
  • Brokerage
  • Chandlery
  • Charter
  • Community Club Organisation
  • Cruises
  • Eating Out
  • Marina
  • Marine Services
  • Realty
  • Sailing Schools
  • Sightseeing
  • Watersports

Meander around the Greek islands and experience the holiday of a lifetime!

flotilla sailing holidays

The Ionian Islands of Greece remain Sailing Holidays’ spiritual home and are just as beautiful as the first time we went there – come and share them with us!

The welcome is as warm as ever and the atmosphere totally unique. Where else in the world can you drift into a village harbour, tie up and walk a few paces to a taverna table?!

Flotilla sailing holidays in the Greek Islands have become the classic way for a host of ‘outdoorsey people’, to have their first go at sailing in the sun.

We have yachts designed to be operated easily and we are in an area that has no tides, very stable weather, and lots of beautiful bays and harbours.

You will have the opportunity to experience many elements of boat handling under the guidance of our experienced lead crews during your week or fortnight.

To be able to meander around the Islands of Greece under sail and in the sun is a rare privilege and we are proud to offer our unique perspective on the area.

Our flotilla sailing holidays are inclusive of flights, local transfers and your yacht for one or two weeks. A typical flotilla consists of between nine and twelve yachts depending on yacht size.

This means that each flotilla group usually consists of between 30 and 50 people of all experience levels. Each of our flotillas is supported by a fully crewed lead yacht offering unobtrusive back-up, local knowledge, informative briefings and assistance where required.

We try to make our first days sail as gentle as possible and will usually only cover 10 to 12 miles. Your lead crew will usually motor-sail to be at your destination in time to take your lines on the quay when you arrive, especially in your first week!

Most evenings you will be moored in a village or marina so there is plenty of time to explore on shore. One evening is set aside for a beach party when the yachts are rafted up close to the beach and you will row ashore in the dinghies. The return journey can be entertaining!

Your lead crew will organise the food and drink and the route for the following day is appropriately short (as the first aid kit does not contain hangover cures!)

During the first day or two of the cruise, your lead crew can soon ascertain whether or not individual yacht crews are competent to go off on their own. If they are satisfied with your boat handling ability, you are free to wander further afield although your safety and wellbeing remain their prime concerns.

If you are going off independently for a couple of days, you will be expected to brief the flotilla skipper on your planned itinerary so that he/she can inform you of any idiosyncrasies of the area you are going to.

Our sailing holiday yachts

All yachts are set up to provide ease of handling in all areas of operation. Sails are kindly cut so they roll up smoothly and there is always the ‘iron topsail’ (the engine) which fortuitously also keeps the beer cool!


There are no significant tides, swell or compass variation to worry about in the areas where we operate our flotillas.

You are never more than 10 miles from land and the good visibility means it is very much eyeball navigation so little need for a GPS when you can see your destination.

Luxury Skippered Yacht Charter

We now have our own ‘in house’ skippered charter yachts. ‘Kalokeri’ (beautiful moment in summertime) is a stunning example of the Beneteau 52.3, with teak decks, television, bow thruster, auto pilot and separate skipper’s cabin.

This is not the least expensive holiday option, but it is certainly the most luxurious in our range of holidays. She is ideal for those with no boat related experience at all, or for those who wish to have a ‘feet up’ holiday while someone else takes responsibility for the yacht.

She will again be cruising the Ionian Islands for 2012, sailing wherever and whenever you fancy. This yacht can also be chartered independently as a ‘bare boat’ by those qualified to do so.

We also now have a 2011 Beneteau Oceanis 50 which has four en suite double cabins, plus a skippers cabin. She is available as a skippered yacht for parties of up to four couples. The saloon table goes down to create another decent bed if you have some singles in your crew.

Usually she will sail with one of our ‘Whole Ionian’ flotillas, but she will also sometimes be chartered for independent sailing.

The 50ft and 52ft yachts are essentially independent but will certainly meet flotillas here and there during the holidays so back up is never very far away. Our crew are kept up to date with local weather anomalies and modern communications are excellent.

So all you ‘big boat’ enthusiasts can now enjoy the same flight inclusive package that is available for our smaller yachts. You can even join up with a flotilla should you so desire! In the evenings it’s nice to meet with fellow sailors in a local taverna. You can enjoy the best of both worlds!