Flotilla Sailing Holidays

Flotilla Sailing Holidays

An Island Sailing flotilla gives the perfect balance of independence and social sailing with the reassurance of support. Our flotillas consist of a group of stylish and modern yachts and catamarans exploring the Greek islands at their own pace with a lead boat and crew.

Flotilla sailing is a great way to enjoy a fun and relaxing holiday around the Greek islands and during school summer holidays they are designed with families in mind.


How an Island Sailing flotilla works

Our experienced and friendly flotilla skippers are all RYA Yachtmaster qualified and provide professional support throughout the week. They give a briefing each morning and chat with you about the cruising plans for the day. With lots of knowledge about the local sailing destinations they can give you tips and advice so you get the most out of your holiday.

The number of yachts in our flotillas allows us to visit all of the best places including some of the smaller and most picturesque ports and bays. You don't sail 'like ducks in a row' but independently meeting up with the other yachts at the end of the day at each destination.

Set sail at your leisure and explore each day at your own pace. Stay in a different port each evening, stopping en route in a small bay or pretty village for lunch and a swim and snorkel.

The lead crew are at the chosen destination each day to make sure that you are moored up safely for the night. Once in port, the evenings are your own to relax and enjoy the company of others in your flotilla or to spend time with your family or friends. You can also join our flotilla on a Learn to Sail holiday.

Our flotillas run from May until the end of September and you can sail for one week or two. Two week flotillas visit new places each week and include free sail days mid-way through.

School Summer Holiday Flotillas

Designed with families in mind our summer school holiday flotillas provide stress-free sailing around the beautiful Greek islands. Explore caves in the dinghy, snorkel to find sunken treasures and spot dolphins. Sail independently as a family or meet up in a bay with other yachts en-route to each evening’s new destination.

Our summer flotillas are a social hub where children can meet up, play on the beach or in a picturesque little harbour and parents can unwind and share their days' adventures. In the evenings your flotilla crew will recommend great places to dine with the other yachts or special places to eat as a family.

Ionian Flotillas

Our Ionian flotillas running in May, June, early July, end of August and September out of the main summer school holidays are ideal for couples, groups of friends and those families with grown up children.

Enjoy the Greek hospitality as well as professional, unobtrusive support from our flotilla crew who will help you to discover the very best places the Ionian has to offer. Our lead crew will recommend the best bays and special places to eat, drink, socialise and relax, often somewhere a little different to the places on the usual flotilla routes.

Flotilla Itineraries

The Ionian island chain lets you choose each day which route you take to the next destination whether you want a shorter island hop or a longer sailing day.

Our specially chosen itineraries visit the best bays, beautiful villages and the nicest tavernas sailing to a different destination each day. Here are a few examples of the places our flotillas visit in the North and South Ionian.

The Ionian Islands

The Ionian Islands are perfect for fun, relaxed and varied Greek island sailing.  The islands offer safe anchorages in picturesque bays with crystal clear water perfect for swimming and snorkeling. Explore fantastic pretty ports on Kefalonia, Lefkas, Corfu and Paxos and discover everything from the ancient greek mythology of the island of Ithaca to the legendary windsurfing destination of Vasiliki.

Sail on one of the latest model yachts or catamarans from our fantastic Lefkas marina base, ideally situated for sailing around the North and South Ionian islands.

Flotilla Sailing Yachts

Our very modern yachts range in size from 31 feet with 2 cabins to 51 feet with 6 cabins with extremely high specifications. We also have new catamaran yachts which offer extra space and luxury.

For more information

Call us on 0330 088 4744 or

Email contact@island-sailing.com