Gay Sail Greece

Gay sail Greece with the leading gay sailing brand, Pride Sailing Holidays.

Pride Sailing Holidays allows the opportunity for clothing optional (nude sailing) between the islands for those that want it  and caters to the male gay audience with our gay and gay friendly crew. Our crew comprise of Captain and host/hostess, so you’re taken care of while on the yacht.

Pride Sailing Holidays offer the best sailing yachts for your private gay sailing experience in Greece, including 4 x double cabins for guests, allowing up to 8 customers and 2 crew. Crew have their own quarters on the boat.

On your gay sailing holiday in the beautiful Greek Islands, you can enjoy nude sailing while we’re underway sailing the gorgeous Greece waters or just sit back and enjoy. Your gay and gay friendly crew cater to your breakfast and lunch while on the boat, so you have nothing to worry about. You can also bring your favorite tipple to drink while on your gay sail too.

When you gay sail Greece with us, we also have optional dress up and dress down theme days, while in the privacy of your private yacht. Your experience is a fun and exciting way to meet new people while sailing the Greek Islands, so either book your private gay sail for up to 8 people on a private charter, or book your private cabin.


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.

Gay Sailing Holidays in Greece

Join us on our exclusive Gay Sailing holiday in Athens, Greece. We have a terrific catamaran and fully crewed, gay charter for you on the most spectacular and most gay sailing holiday on the market! 

We have the most exciting itinerary, theme days, host to prepare your onboard meals and Friday and Saturday night in Athens! 


We are only offering a limited number of weeks for our Athens Gay Sailing Holiday in August

8th August 2020

15th August 2020


We are offering a round trip, starting and ending in Athens, stopping in the party island.


Because you'll have the time of your life, on an unforgettable gay island hopping vacation.


We include everything you could want, for the most fabulous gay vacation in Greece, ever.

♂ Champagne arrival

♂ Seven days/nights on your own private yacht in Greece

♂ Theme days for extra excitement, including 'Speedo / Nude Sunday' & 'Wig Wednesday' 

♂ Sail the Greek Islands on a Private Catamaran

♂ Gay-friendly crew: Skipper and host

♂ Your host will escort you to all the local gay spots in all the ports: beaches, clubs etc

♂ Your host will prepare your breakfast & lunch daily
♂ Snorkeling gear is available for underwater fun
♂ You can learn how to sail with your qualified skipper, or just sit back and enjoy
♂ You will have your own yacht with your friends or make new ones
♂ Always a small group on board (max 8 guests)
♂ All onboard costs are covers: fuel, water & port/marina charges, tourism taxes, linen and final cleaning fee, etc
♂ WiFi 
♂ No hidden charges or 'departure taxes'

Join us in Mykonos at the marina, and check in at 17:00.

 Saturday: Mykonos

5pm: 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?!

Sunday: Paros 'Speedo Sunday'

After breakfast, we'll set sail for Paros to enjoy the pitureesque 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 favourite speedos and get ready to walk down the catwalk. No gay sailing trip is complete without your speedos.

Monday: Ios 'Naked / Underwear Monday'

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

Tuesday: Santorini (optional ferry)
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. 

Wednesday: Ios 'Wig Wednesday'

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! 

Thursday: Naxos

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.  

Friday: Mykonos 'White Party'

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! 

Saturday: Mykonos 

Sadly, it's time to say goodbye.  Check out is at 9am.

Gay Sailing Itinerary



Gay Sailing Holiday Greece 2021



The boats we operate on our Gay Sail in Greece are the French built:

Lagoon 42




© 2015-2020 Med Sailing Holidays group 

Australia: +61 (02) 8005 0410

New Zealand: +64 (09) 889 8304

UK: +44 (0) 20 3289 9366

USA: +1 (347) 329-4417

Other group brands:

  • Med Sailing Holidays
  • Yoga Sailing Holidays

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Home port:  Marina Kaštela, Split, Croatia

As seen on:

Gay Travel
DNA Magazine
Gay Holidays
Gay Holidays Croatia
Gay Voyageur

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