Find your perfect sailing holiday!

Over 80% of our guests come back again, let us match you with something unforgettable.

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Flotilla Sailing Holidays

Our Flotilla Sailing Holidays

Flotillas give you the freedom to skipper your own yacht; with a support crew on hand; and a fun group sailing alongside. Whether you’re new to sailing or know your way around a chart plotter, this is the easiest way to explore the coast, meet great people, and enjoy stress-free sailing.

Sail Your Way, We're Here to Help

You’re in control of your boat. The lead crew handles route planning, mooring assistance, and daily briefings — so you can focus on sailing, not stressing.

Drop Anchor, Unwind, Join the Fun!

Cruise solo by day, then catch up with the flotilla for dinner, drinks, or a beach party. It’s social when you want it, relaxed when you don’t.

No Experience? No Worries

First time on a yacht? Hire a skipper and get straight into it. Qualified sailor? Just book and go. Flotillas work for everyone — from total beginners to seasoned skippers.

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Our Flotilla Destinations

Set sail on one of our Flotilla Holidays and discover the most beautiful corners of Greece. Each route handpicked for it's scenery, charm, and sailing conditions. Wherever you choose to sail, you’ll enjoy crystal clear waters, friendly locals, and plenty of time to soak up the magic of the Greek Islands.

Our Yachts

Customer reviews

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Another superb holiday provided by Sailing Holidays. All of the pleasures of Greek island hopping with none of the hassle.  

Martin

We’ve sailed with Sailing Holidays from when our kids were toddlers to now coming away with adult kids and even grandkids on one occasion. We love the laid back approach allowing us to feel in control with the lead crew being there to assist and facilitate. It’s a delicate balance and sailing holidays gets it just right. 

Sara

Excellent holiday with a family run company. Wonderful that you have real people to talk to at the phone and when abroad. If only other holiday companies did customer service like you!

Keith

Great boats and lead crews, the most relaxing activity holiday you can have.

John

Thank you Sailing Holidays for all your hard work and great sailing memories, you’ve made thousands of families happy with all your lovely boats, crews and sailing experiences, keep up the good work.


Graham & Vee

If you have never been on a Flotilla with Sailing Holidays, get booked and find out why this company is head and shoulders above the rest.  It's in the detail, and the detail counts.

Mike and Sally

Also all of your boats have in-mast furling which, as we're not as young as we once were, does make hoisting and reefing the main a lot less faff. 

Sue and Andy

Sailing Holidays are truly glorious. As a company, sailing holiday, flotilla staff and an all round brilliant experience. We are repeat customers over many many many years, from our honeymoon in our 20's to now in our 60's. We live in New Zealand now, and make the journey across the world. We will be back :)

Clare and Bruce

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.

Anna

We do own our own boat in the UK. However, Sailing Holidays takes all the worry out of sailing abroad in the sunshine. Although we would check on pilotage, routes and hazards, having a lead crew with local knowledge and being available to take lines ashore is a big bonus. 

Keith

Just home after 2 weeks sailing with Sailing Holidays and we loved every minute of it- we hadn’t sailed in 6 years and felt rusty and slightly nervous but the Lead Crew were so supportive and encouraging that we quickly found our feet. We’ll be back!

Kim

Learn to Sail in the Sun

Keen to build your skills and confidence?
We run RYA sailing courses in the Greek islands!

RYA Competent Crew

Ideal for beginners, this course teaches essential sailing skills to become a confident and capable crew member. 

RYA Day Skipper Practical

Learn to take charge as a skipper, mastering navigation and boat handling in the calm waters of the Ionian.

RYA Combined Course

A comprehensive two week course that combines your Competent Crew and Day Skipper qualifications.

RYA VHF (SRC) Course

Gain the skills and license to operate marine VHF radios safely and effectively.

Yacht charters

Check out our Yacht Charter Agency Division for independent sailing options in Italy, Croatia, Turkey, Greece and Spain.

Bareboat Yacht Charter

Best suited for experienced sailors looking for complete freedom and flexibility of destination in the Mediterranean, as well as a wider selection of Yachts.

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Skippered Yacht Charter

Perfect for those who want to relax and enjoy sailing with the guidance of a professional skipper, or for people who do not hold an RYA Dayskipper or ICC qualification.

Luxury Crewed Yacht Charter

Best suited for people who want a true luxury experience, extra space and all the creature comforts of a villa.

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