Pride Sailing Holidays is super-excited to be offering our Gay Sailing in Mykonos, Greece!  The Gay Mecca of Europe must be one of the top destinations for any gay traveler. Pride Sailing Holidays is proud to be offering a Mykonos itinerary, which starts and ends the trip in Mykonos. 

We have an action-packed 7-day itinerary, sailing south to Santorini and calling into Paros and the party island of Ios on the way. We have theme days to spice up the afternoons, including 'Speedo Sunday' 'Undie Monday' and the famous 'White Party' on Friday night in Mykonos! 

So either gather your friends for a private charter, or book a private cabin, pack your best speedos and book your tickets! Gay Sailing has never been so good. 


Great crew who take great pride and creating an awesome experience in a beautiful place. I will be back many times in the future.


So much fun. Johnny and Reno are the best!


Joe & Olivia were fantastic. Amazing holiday on the Cat around the Greek Islands.


Sailing Greece highlights

  • The best Greek sailing itinerary in the market (in our opinion)

  • Full crew provided on all voyages (Captain & Hostess)

  • Book a cabin for a fraction of the price of a whole boat, or

  • Book a private charter for you own group

  • Completely hassle free - we'll take care of everything 

  • No previous sailing experience required

  • Get away from the hordes of tourits

  • Learn to sail (if you want) with your qualified skipper

  • Daily swim stops in the crystal clear water

  • Trips suitable for professionals, couples, families and a mature audience

  • Explore Kefalonia and visit the world famous Myrtos Beach!

  • Swim inside the Blue Caves (Lefkada), explore Melissani Cave and enjoy the breathtaking beaches.

  • Check out the famous Porto Katsiki beach

  • Dine in Fiskardo, with some of the best restaurants, ever

  • Let your taste buds come alive with the local food and wines

  • Wander the streets of Vathy, Ithaka the home of Odysseus from Homer's Odyssey

  • Take in the sights and relax as we sail the coast

  • Golden sunsets and sunrises like nothing you've seen before

  • A sky full of stars at night, with no light pollution

What's included?

  • Champagne arrival

  • Seven days/nights accommodation on your luxury private yacht

  • Luxury Lagoon 42 catamaran

  • Champagne arrival

  • Early check in

  • Full crew: Skipper and hostess

  • All your onboard costs included:

  • Your weekly marina & port fees

  • Fuel (up to €200)

  • Final cleaning fee (€250)

  • Local taxes

  • Half board: your hostess will prepare your breakfast & lunch

  • BYO alcohol

  • Snorkelling gear

  • Learn how to sail or test your skills with your qualified skipper

  • A private yacht for a fraction of the cost to do it yourself

  • Always a small group on board

  • Wifi (Limited data)

  • No hidden charges or 'departure taxes'

We offer the most inclusions and the best value for money!


You will start your Greek Islands sailing holiday in Lefkas town on Lefkada Island. If you arrive early, you can explore the wonderful Greek Island and her beautiful postcard beaches.


If you have a day or two on the island before your trip, be sure to hire a car and explore the island, you'll have fantastic views, perfect beaches and you'll be spoiled for choice with the local restaurants.

After checking in, we're off to Meganisi to start your Greek Island sailing holiday.

Our first stop of your Greece sailing holiday is Meganisi.  Meganisi offers the charm of a small port, like only the Greeks can do!

We will be berthing in a family owned and operated restaurant and pier. Nothing says Greek hospitality like the locals running around in preparation for us. We will dine on the water's edge as the sun sets over the bay.

In the morning we'll set sail off for the Blue Caves of Lefkas to kick-start your Greek Sailing Holiday in style! Prepared to be amazed.

Sailing the Greek Islands is a magical event, so while on your yacht charter, we will take you to a place of legend; Ithica, the home of Odysseus, the King who left his wife and home in pursuit of victory at the battle of Troy.


Ithaca is a peaceful island, ideal for relaxing and enjoying a slower pace of life and some of the meals the local tavernas prepare stay true to the ancient recipes of an older time.  

On our way to Vathy, we'll stop off to explore the Blue Caves, so get your swimmers on and be ready.

Whilst on your private yacht for the week, no trip is complete without stopping at Kefalonia, which is the largest island in the Ionian Sea and has so much to offer.


Famous for it’s exotic beaches, including Antisamos and Skala are stunningly beautiful beaches we’ll pass on the way to Sami, where you can make your way to the Melissani Cave, lounge on the glorious beaches or explore the island at your own pace.  

We arrive early in port today, which gives you the opportunity to see the Melisanni Caves, scooter to Myrtos Beach or take a wine tour. Whatever you do, you'll have the opportunity to see this beautiful Greek island.

Fiskardo must have THE BEST RESTAURANTS in the Ionian!  We almost need to stay a week to explore all the restaurants here.  This isn’t a secret and a lot of boats come to this special little place, so we need to get there early if we want to get a place on the town quay. No Greek sailing holiday is complete without stopping here for dinner.


Greek Island sailing holidays are about a unique experience and Fiscardo at night takes on an entirely different perspective. The lights, the old buildings, cafés, bars & restaurants all combine to provide a magical Mediterranean atmosphere. Of  all the villages on Kefalonia, Fiscardo stands out as having a unique ambience, especially on a summer evening.

When you think about sailing the Greek Islands, you think about clear water, beautiful beaches and white cliffs.  This is it. We sail you to Porto Katsiki beach on Lefkada Island, which is one of the most beautiful Greek beaches.  It is also in the top of the list of best beaches in Europe each year. You will absolutely fall in love with the beach and won't want to leave, ever. We will stop for lunch and swim before heading to Sivota Bay.


Greece sailing holidays are know for protected harbours, and Sivota is one of the nicest natural harbours and one of the most picturesque fishing village in whole Ionion.  After parking the boat, you’ll stroll the streets soaking up the special atmosphere of the magical bay. 

We'll sail the catamaran to Papa Nicholas Caves where it’s said that it was a secret hideout during World War II for the submarine Papanikolis of the Italian armada. After a swim and exploration, we’ll sail to a final stop for the trip.

We have a day of smooth sailing, beaches, relaxing and soaking up the sun before heading to Kalamos.

Kalamos is a small town, which has small town charm for dinner on the water's edge.

When we sail back to Lefkas, we’ll stop in the protected bay of Ormos Vrako on the mainland.


There is a cocktail beach bar, where you can enjoy the music, lap in the shallows of the water or grab your snorkel and explore the rocks and the surrounding bays.  Sometimes 'Sailing the Greek Islands' means laying on the beach with a cocktail.


What a superb way to end your week sailing the Greek islands, before heading back to the marina by 6pm. 

All good things must come to an end and it's time to say goodbye.

Check out and disembarkation is at 9:00

If you have the time, it's always nice to stay in town for a day or two to enjoy the island life. Perhaps a villa with an infinity pool, overlooking the sea speaks to you?


When you book a sailing holiday in the Greek Islands, it’s important that you factor in all the running costs of the trip, so you have an accurate quote, you have the most value and you’re not surprised with unknown charges on the day.


If you are booking at sailing holiday for your friends and family in the Greek islands, you might want to consider a private charter so your group have the exclusive use of the boat. This way you also have more control over your in

inclusions and overall trip.

The alternative to booking a private charter is booking a cabin charter. This way you get all the benefit of a private charter for a fraction of the price. It’s advisable to look what is included in the price, as much as what is not.


It doesn’t matter if you’re booking a private charter or a cabin charter for your Greek sailing holiday, we include everything you could need on your trip. Because of this, at first glance our fully crewed sailing holidays may appear to be more expensive than the other operators, however you will discover that we offer more value for money, giving you more bang for your buck.




Pricing is based on 2 people sharing a double cabin.

Please make an enquiry if your preferred dates aren't available.


Master Cabin

Forward Cabin

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Zinas Kanther, 16

Karantoki Building

5th floor, Flat/Office 13

1065, Nicosia, Cyprus

Australia: (02) 8005 0410

New Zealand: (09) 889 8304

UK: 020 3289 9366

USA: (347) 329-4417


Organisation number: HE 341903


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