Ultimate sailing Flotilla holidays around the Greek Islands

Island hopping around the crystal clear waters of the Greek Islands is a dream for most of us, but imagine you aren’t just sitting back and following someone elses course, but joining the crew of your own yacht on a flotilla sailing holiday is beyond amazing! We’d never heard of this concept before, but it the idea makes us want to grab our deck shoes and head off to sailing school!

What is a Flotilla sailing holiday:

A flotilla sailing holiday basically consists of between 4 – 10 yachts that sail together. The group of yachts is lead by an experienced skipper who has planned out the route and checked the weather conditions and other possible hazards for the day. Each day the lead skipper will usually allow the rest of the group to depart first and will then sail ahead to reach the destination first, he will save space for the rest of the group to moor and is there to lend a hand if needed. With all of this in mind, a Flotilla holiday is ideal for novice skippers who can gain more sailing experience without having the stress of planning and feeling alone. It is also ideal for experienced skippers who just want to relax and enjoy there holiday and take in the beautiful surroundings without the hassle of planning. Having your own space and the time to really enjoy these settings at your own pace also makes them ideal family holidays too.

Perfect destinations for flotilla holidays:

The Greek islands are a perfect destination for complete beginners and novice sailors to have a go and enjoy the stunning scenery. They are also a perfect place for the experienced sailor as they can relax and make the most of the gorgeous surroundings.

The Greek Islands

If you decide to have a Flotilla holiday in the sunny islands of Greece there are a few different options to choose from. There are the Ionian islands, Sporades islands and Saronic islands, so plenty of choice for inexperienced sailors looking to hone their skills in paradise settings and without the stress. They are also an amazing choice for the more experienced sailor who either wants to relax or is able to cover more distance.

The Ionian Islands

The Ionian islands have the best variety of Flotilla sailing holidays as they cater for all levels of experience. They especially cater more towards novices as the other island regions can be more challenging, but experienced sailors can still be thrilled by from what the Ionian islands have to offer. In the Ionian islands you will be treated to beautiful harbour villages which are home to very welcoming local people, you will also be able to feast your eyes upon multi-coloured fishing boats and also enjoy some time in the amazing local tavernas. The Ionian islands are usually best enjoyed for either 1 or 2 week holidays, depending how many islands you want to visit. The most popular destinations include: Ionian mainland, Lefkas island, Kastos island, Kefalonia and Corfu island and many more. So there is definitely enough choice to keep you entertained and coming back for more!

The Saronic Islands

The Saronic islands are a great destination for those who have sailed around the Ionian islands and want a slight step up in challenge, as these islands boast slightly stronger winds. This can make the sailing feel even more exhilarating.  But it’s not only the conditions that should persuade you to choose these islands for your Flotilla holiday, as the whole area of coastlines has amazing places to explore. You can also have the chance to swim in the crystal clear waters with turtles and taste some world class wine in an ancient byzantine city all in the same day! Some Saronic islands highlights are: Palaia Epidavros, Nea Epidavros, Vathi, Hydra island and Ermioni.

The Sporades Islands

The Sporades islands are located in the Aegean sea and lie just north of Athens. They are also known for the famous summer meltemi winds. The islands are home to the national marine park of Alonissos where dolphins, rare seabirds and the endangered Mediterranean monk seal all take refuge. Because of the summer meltemi winds the Sporades islands often attract keen sailors who want to challenge their abilities. After all of the excitement trying to tackle the strong winds, the Sporades islands offer a chance to escape all of that for a while and enjoy clear waters and beautiful bays on some of the more remote islands which are situated more towards the east. Spend these nights anchored to stunning uninhabited and sheltered bays where all you can hear is the relaxing sound of the water gently lapping on the beach. The highlights of the Sporades islands are Skiathos island, Skopelos island, Alonissos and Kyra Panagia.

Have you ever considered flotilla holiday’s or sailing trips?

We’ll be honest, in the past it might not have been on our radar, but having spent a LOT of time on a variety of ships and boats over the course of our time in Asia and Australia we have come to really appreciate the freedom and different perspective it gives you. We might not be quite ship shaped and ready to sail, leaving our backpacks at home for the deck shoes and cocktails, but after months on the road we can certainly see how we might change our way of travelling for something more relaxing in the future. These unforgettable Greek island flotilla holidays have to be the ultimate inspiration to set sail! 

Book your accommodation here

Hey, you’ve got your Travel Insurance sorted haven’t you?

Travelling and especially backpacking is a wild adventure, but make sure you are covered just incase something goes wrong, which if you’re living it up to the fullest it’s always a possibility!
Check travel insurance prices with World Nomads here!

Leave a Reply

Oldest Most Voted
Inline Feedbacks
View all comments
2 years ago

Hi Nic,

Stunning! The water alone is eye-popping. Not been on a flotilla but it is on my list of things to do.


2 years ago
Reply to  Ryan Biddulph

Cheers Ryan!