Sail your own yacht through the Greek Islands as part of a small, sociable flotilla—led by our friendly crew and filled with unforgettable moments. Whether you’re a seasoned skipper or a complete beginner, this is sailing with all the freedom you want, and all the support you need.
What is a flotilla holiday?
Flotilla Holidays are all about freedom, fun and friendship. Picture this: you’re at the helm of your own yacht, the sun rising behind you as you leave a quiet bay. You’re part of a small group—usually 10 to 12 boats—meandering from island to island at your own pace.
Each morning starts with a relaxed briefing from your lead crew, who share the day’s suggested route, tips on hidden gems, and help with anything you need. Then it’s time to cast off. You can sail together or head out solo—there’s always a friendly voice on the radio if you have questions.
Swim in turquoise coves. Lunch on deck. Wander harbour towns where locals greet you like old friends. End your day with a taverna dinner, clinking glasses with your flotilla mates as the sun goes down.
Discover
Who are flotilla holidays for?
Sailing made simple, even if you’re brand new to it.
Our flotilla holidays are for anyone who loves the idea of exploring Greece by yacht, with the comfort of a supportive team and a sociable sailing community. Whether you’re a seasoned skipper or brand new to boating, there’s a flotilla for you.
We welcome:
- Experienced sailors looking for an easygoing route and great company
- Families who want fun-filled days, safe sailing and splashy adventures
- Groups of friends keen to soak up the sun, sea and taverna life
- Solo travellers joining friends or crewing with others on shared adventures
Our flotillas are about making memories, sharing experiences and embracing everything the Mediterranean has to offer at your own pace, in a safe and friendly environment.
A lead crew, for you
Every flotilla is supported by a dedicated lead crew—your Skipper, Engineer, and Hostess—based on the lead boat that sails with the group. They’re not just there to keep things running smoothly; they’re the friendly faces who make your holiday feel effortless.
Here’s what they’re here for:
- Practical support – helping you moor, fix a snag, or understand the day’s route
- Local knowledge – recommending great swim spots, tavernas, or hidden coves
- Community spirit – bringing the flotilla together with optional social events
They’ll be as hands-on—or hands-off—as you like. It’s your holiday, and they’re there to help you make the most of it.
Picture Your Flotilla Adventure
Sometimes words aren’t enough. Take a look at what life looks like on one of our
Flotilla Holidays—from sun-drenched decks and peaceful anchorages to lively
evenings with new friends.
Our Flotilla Destinations
Set sail on one of our Flotilla Holidays and discover the most beautiful corners of Greece—each route handpicked for its scenery, charm, and relaxed sailing. Wherever you choose to sail, you’ll enjoy crystal waters, friendly villages, and plenty of time to soak up the magic of the Greek Islands.
Our Flotilla Holiday Options
We know everyone travels differently, so we’ve designed our Flotilla Holidays to be as flexible as possible. Whether you’re after a pure sailing adventure or something with a little extra comfort, we’ve got you covered.
Our Yachts
What Our Sailors Say
Huge thanks to our Lead Crew for making it such a fantastic week. We've done bareboat before but never a flotilla, but realised that we will now probably only do flotillas because of the special touches they add and making it all so easy so we can focus on sailing and having fun.
Some beautiful, picturesque harbours and fishing villages. We particularly loved Karnagios, Meganisi and Kioni.
Your own boat, sailing from island to island in the sunshine. Meeting up with new friends every evening......What's not to like!
Book With Confidence
When you book one of our Flotilla Holidays, you can relax knowing your trip is
financially protected and professionally managed.
