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Pride Sailing Holidays is super-excited to be offering our Gay Sailing in 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. 

Gay Week

Gay Week



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!

sailing holidays


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


Sail Greek Islands Porto Katsiki

Sailing Greece highlights

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

  • Full gay-friendly 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 Paros and visit the infamous gay island!

  • Check out the famous Santorini (optional ferry) and it's wonders.

  • Party in Mykonos, with some of the gay bars ever!

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

  • Wander the insta-perfect island of Naxos.

  • 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

Mykonos (Updated)

What's included?

  • Champagne arrival

  • Seven days/nights accommodation on your luxury private yacht

  • Luxury Lagoon 42 catamaran

  • Champagne arrival

  • Early check in

  • Full gay-friendly 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!

Gay Sailing Greece Inclusions
Pride Sailing Celebration

Check into your private yacht and meet your crew and fellow Gay Sailing guests

Enjoy a welcome glass of prosecco before we go out for a night in Mykonos.


There is the option to meet your fellow guests at the marina at 13:00, drop off your bags then head to one of the many gay beaches.


What better way to start your Greek gay sailing holiday?!


After breakfast, we'll set sail for Paros to enjoy the picturesque town for leisurely strolls before dinner in the postcard town.  


Although Paros isn't known as a gay island, it's very beautiful and extremely welcoming to sailors from near and far.

On the sail down to Paros, it's 'Speedo Sunday'! so break our your favorite speedos and get ready to walk down the catwalk. .

Gay Sailing Holiday Fun

We set sail for the party island of Ios and on the way, we have our 'Naked/Underwear Monday' so make sure your favorite Calvins are ready.


Ios is a super-fun island, where you can enjoy the beaches, restaurants and dance the night away. Check out the first gay bar in Ios, called 'Pride' and give them our support. BTW we love the name 'Pride'.

Gay Sailing: The Two Bad Tourists

Santorini is a must see if you're in the area, sadly weather and suitable berthing options prevent us from taking the boat there, however there is an optional ferry that can take you there in record time.


Hire a scooter or car and explore the island for magical sunsets and the most breathtaking vistas ever. 

Pride Sailing Snacks

We make our way back up towards Mykonos, stopping off in Ios again to enjoy the beautiful beaches and for another night out dancing, should you feel like it.


On the sail up, we have our 'Wig Wednesday' where we have some fun with wigs, or bring your own outfit! 

Sailing Greek Islands Porto Katsiki

Naxos is a beautiful island and an amazing town.


it's perfect for wander the streets, capturing your Insta-moments and enjoying the beauty of the Greek Islands.

Get a chance to get amazing photos for your social media platforms

Gay Sailing Activities

As your Greek gay sailing holiday is closing to an end, we've saved the best for last with the 'White Party'!


Don your best white outfit and we'll get warm the party with drinks on the boat before heading into the town for dinner and hitting the gay bars and clubs in Mykonos, with our very own Pride white theme. Watch out boys, here we come! 

Pride Sailing Holiday Adventure
Check out

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.



Gay Sailing Greece Dates

Pricing is based on 2 people sharing a double cabin.

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

Gay Sailing Greece Book Now
Gay Sailing Greece Boat Layout

Master Cabin

Forward Cabin

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