Book Now
What our travellers say

Beautiful coastline, delicious food, thrilling sailing and days filled with belly-laughing fun.

two ladies sit on the stern of a yacht in dresses

A luxury sailing holiday is more accessible than you might think…

Exploring the Greek islands on board a private luxury yacht is the ultimate holiday experience.  It’s everything you need, in one place – water sports, private chef, unlimited swimming, powerful yacht, 5* service – and more.

Life on board is easy, and luxurious.  It’s a holiday for those who want to be pampered, and absorb the very best that the Greek islands have to offer.

But what if you’ve never been sailing before?  Well, that’s no a problem.

Your professional crew will take care of everything, so sit back on a deck chair (quite literally) sip a cocktail and relax into the holiday of a lifetime.

Plus, we’ll walk you through when is the best time to go sailing in Greece and even what to wear for your first sailing holiday.

It was an overwhelmingly fabulous cruise. We had gathered an excellent coterie of good citizens from Australia, but it was the crew who really made it all come together.

- Jim, Australia

Sum up a sailing holiday in a nutshell?

Think comfortable, air-conditioned cabins with en-suite bathrooms.

A professional skipper there to do all the yacht work (or show you the ropes if you want to get involved…)

A private chef to prepare delicious meals in stunning locations.

Here’s what to expect in a typical week on board a sailing yacht.

Plus, each yacht has its own speedboat with water skis, wakeboard and a ‘ringo’ donut for the thrill-seekers.

Stand-up Paddleboards and a windsurf rig, snorkelling fins, masks and fishing gear in the ‘garage.’

& for the ultimate luxury sailing experience, why not book a deck massage with our on-board spa experience?

The nitty gritty

Prices start from £1,720 per person, based on 8 people hiring the yacht exclusively.

We also run cabin charters, if you don’t want to rent the whole yacht – which is a great way to try sailing for the first time.

This price includes your yacht, skipper and chef, all fuel and marina fees, private speedboat, unlimited watersports, taxes and local charges.

The extras are flights, transfers, carbon offset for your trip, and a crew gratuity.

Trips are half board so for dinner you cam either step ashore to a traditional Greek taverna and soak up the heady Greek summer atmosphere, or, for a break from the Bouzouki, eat on-board anchored in a tranquil bay, with food prepared by your private chef.

Got questions?  We’ve got answers.

people enjoying a speedboat ride

Where will you sail?

Routes and itineraries are completely flexible, with multiple start and finish destinations available.

Don’t worry about getting the most from your sailing holiday: you tell us what you like, and we’ll sort it!

Experience a blend of culture, history, food and a state-of-the-art yacht designed for ultimate luxury and comfort.

“Absolutely superb. A five star service throughout booking and the holiday. Each person involved from Fleewinter exceeded my expectations.”  D. Davis, July 2023


These are some examples of where you might head in a one-week holiday. While exact routes are dependent on the weather of course, your crew will work with you to create the perfect trip!

Got questions? We've got answers!

Join us for the experience of a lifetime.

To take the time to find out what makes you tick

Create a completely personalised itinerary with unlimited revisions

Offer support every day before you fly and total support on holiday

Welcome to Argentous, Lunous & Aurous

Welcome to booking a luxury sailing holiday!


Villages visited


Happy customers


Miles sailed
20 minutes from the international airport, Corfu is our home berth
The Faraway Islands
'Faraway' means nothing to our powerful yachts. Head upwind and explore these gems of the Ionian
"Emerald Bay"
Explore beautiful coves and caves. Only accessible by boat...
If you need a "break" from the peace and quiet, spend a night or two with all the other super-yachts in Fiskardo. Boutique shops and dozens of restaurants make it great for people watching.

Your adventure starts here!

Do you fancy having a chat about Luxury Sailing Holidays? Personally, it's one of our favourite things to talk about.

Award-winning and fully-protected holidays
Fleewinter wins an AITO award for customer service
Itineraries & Destinations