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14-Day Gay Sailing Cruise in Central Cyclades

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Discover 10 Greek islands in a Gay-Only Sailing Cruise

  • Sunday to Saturday
  • Capacity : 12
  • with Skipper
  • May '20 - Oct '20
  • Cabin charter
  • Departs from Alimos, Athens

Discover the Greek myth in 10 of the most beautiful islands in the world in a luxury crewed sailing yacht and live the ultimate Gay Holiday Experience. The next two weeks will be unforgettable! You are about to live an amazing adventure, exploring magnificent islands and experience Greek culture.

Cyclades, the most famous island group in the Aegean Sea comprises some of the most beautiful islands in the world! Gorgeous sandy beaches, architecture in white and blue, traditional lifestyle, folk music, warm, hospitable people and barren landscapes with isolated chapels turn a trip to the Cyclades into a lifetime experience. Millions of Greek and foreign visitors come to the Cyclades every year to enjoy the dazzling light and the crystal blue waters, in the quest of the paradise on earth. Relax in the sun and enjoy the sailing as your experienced skipper guides you through deserted bays and famous archaeological sites.

Sail from Athens to Sounion, Kea, Kythnos, Syros, Tinos, Mykonos, Naxos, Paros, Sifnos, Serifos and Kithnos before returning back to Athens

Day 1: Athens to Sounio

The journey starts in the best possibly way! Sounio, located on the southernmost tip of Attica, is best known for the temple of Poseidon, the ancient Greek god of the sea. Poseidon dominates Attica where the horizon meets the Aegean Sea. Indulge yourself with a refreshing swim in the small beach by the foot of the temple of Poseidon. The breeze of the ancient history will make you feel calm, as you will become a small part of it. Don’t forget to taste some fresh fish and seafood in the local tavernas.

Day 2: Sounio to Kea

The scenery changes as you approach Kea. Kea is one of the closest islands to Athens, traditional and cosmopolitan at the same time. The warm atmosphere, the local food and the beautiful Cycladic scenery make Kea special to its visitors. Its traditional vibes and quiet beaches offer relaxing moments. While being in Kea, you should also visit the beautiful beaches of Koundouros and Otzias.


Day 3: Kea to Kythnos

Kythnos will impress you with its Cycladic architecture, traditional villages and the long beautiful beaches. Almost all beaches feature crystal clear waters and white sand, while most of them are unorganized and undeveloped. Of course, don’t miss the chance to swim in the most popular beach of Kythnos, Kolona, which is actually resembles a strip of golden sand that connects the islet of Agios Loukas with Kythnos. It’s one of the most beautiful beaches on the island and a must-visit for any traveler!

Day 4: Kythnos to Syros

Syros, one of the smallest islands of Cyclades, is the crossroad for Greek tradition and western influence. Ermoupolis (meaning “the city of Hermes”) is the island’s capital town and most of the nightlife is situated in Ermoupolis. There are lots of bars and clubs there, but the partying is more relaxed than on the “wilder” islands. You should definitely taste the local food in gay – friendly restaurant “Seminario”.

Day 5: Syros to Tinos

Tinos resembles the simplicity, the serenity and the beauty of Cyclades. The island stands out for its hills, its enduring villages and friendly villagers, its wealth of natural beauty, its game between shadows and light, its artistic wealth of painters, sculptors and their works. Tinos is the ideal place for nature lovers, architecture, art and tradition, and the perfect answer to the relative expectations. In the island there are several small villages that are worth to visit. Don’t leave the island before you visit Kolympithra beach! Kolymbithra is a beautiful bay located 15 km from Tinos town. It consists of two beaches, equally beautiful and well protected from the strong winds.

Day 6: Tinos to Mykonos

It was about time to reach Greece’s most famous cosmopolitan island. Travellers from all over the world come to Mykonos for its unique lifestyle, its legendary nightclubs but also its beautiful beaches and water sports. This Greek island is ranked among the best gay destinations in the world, especially for summer holidays. Mykonos has a certain gay lifestyle,

which is not like any other place in the world, combining luxury with fun and beauty. Visit the upcoming Gay Beach hot spot of the island is definitely the ‘JackieO Beach’ at Super Paradise, which stands out as one of the most prestigious gay beach bars in the world.

Day 7: Mykonos to Naxos

Reaching Naxos island you will be fascinated by its combination of high mountains with green valleys, amazing seascapes and traditional villages perched high on mountain tops. The main characteristic of Naxos is coexistence. You can see beautiful old churches, monasteries and at the same time Venetian castles and the Cycladic architecture. Don’t miss the chance to taste Naxos local cheese and swim the gay friendly beach, Aghia Anna.

Day 8: Naxos to Paros

Paros combines natural beauty, beaches with crystal clear waters, Byzantine footpaths connecting traditional villages and breathtaking landscapes. The island is located at the heart of the Cyclades and is one of the most loved destinations in Greece. Paros offers its guests a cozy cosmopolitan environment that includes walks on the beach, cushy sun-beds under the hot sun and rejuvenating dives into the clear waters of the Mediterranean sea.

Day 9: Paros to Sifnos

Sifnos is known as the island of flavors, with unique traditional villages, organized or secluded beaches, and 227 churches spread around the island is just waiting for you to discover it! Sífnos is the centre of pottery in the Cyclades since the first samples that were found here are dated back to the Early Cycladic period. Stroll around the island and don’t forget to take a selfie at picturesque Kastro area.


Day 10: Sifnos to Serifos

Serifos the “iron island” of the Cyclades stands out, in its unique way and beauty, enchanting the visitors at first sight. The island of Perseus and the Cyclopes is the ideal destination for a relaxing day among the Aegean Sea. The island keeps untouched the Cycladic architectural tradition with white and blue houses, making the island look like a Greek miracle. Take a walk in Chora and get inspired from the architecture style and the breeze of this elegant small town.

Day 11: Serifos to Kythnos

Here we are again to this beautiful island! There are many things you didn’t do the first time you were here and now it’s probably the right time to make it up! During the day a hike around the island will bring you in front of ruined castles, chapels and beaches. Take a walk in the picturesque villages Chora and Driopida and watch the sunset, while drinking a sweet cocktail.


Day 12: Kythnos to Athens

This is might be the last stop of the cruise, but the journey begins now! Athens, the land of the sun, offers an unforgettable holiday experience with limitless choices. This city is the historical capital of Europe. Inhabited for more than 3,000 years, Athens is widely known as the cradle of Western civilization and the birthplace of democracy. There are so many things to do in this beautiful capital. Stroll around the city center, visit the iconic Parthenon monument, meet beautiful Athenians, climb at Lycabettus hill to enjoy a panoramic view of the city and enjoy the vivid nightlife of Athens!

Enjoy the Comfort of our Sailing Boats

Our sailing boats, a Bavaria 49 monohull and a Lagoon 38 Catamaran feature the best sailing qualities. With spacious interior, our sailing boats provide exceptionally ample room and remarkably generous stowage, which makes it ideal to explore the Saronic in the most relaxing way. Imagine a great day on the water, sipping with a sweet cocktail, relaxing in quality materials and comfort.

Read more about our sailing boats


Season 2020: 30th of May 2020 - 3rd of Oct 2020


Period Bavaria 49 Monohull Lagoon 38 Catamaran
26th of July  -28th of August 2750€ per person 3400€ per person
20th of June -25th of July & 29th of Aug. – 18th of Sept. 2590€ per person 3100€ per person
30th May- 19th June & 19th Sept. – 3rd Oct. 2425€ per person 2925€ per person

All prices are for cabin charter per person/week. All cabins are double occupancy per cabin. Single supplement (single occupancy of a double cabin): + 65%

Please, make sure to read the cabin charter terms and conditions.

If you are interested in private charter please follow this link: https://gaysailinggreece.com/tour/private-charter 

Details & Information

The ultimate Gay Holiday Experience begins in Greece and welcomes both first-timers and more experienced sailors on board! Prepare yourself for an amazing two weeks sailing adventure in the Aegean Sea.


Alimos, Athens (Google Map)

Price Includes

  • Your yacht (while availability remains).
  • Your crew (skipper and hostess).
  • Welcome drink.
  • On board meals (breakfast & lunch).
  • Fuel.
  • Marina fees.
  • Water.
  • Linens.
  • Dingy & outboard.
  • Final cleaning fee.
  • Taxes

Price Excludes

  • Restaurant dinner.
  • Excursions.
  • BYO alcohol/mixes.
  • Crew gratuities.
  • Departure taxes.
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We would like to inform you that due to the Covid-19 pandemic we have not schedule any cruises for summer 2021. Please, stay tuned for summer 2022.
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