Subscribe to our Gay Travel Newsletter here

The Island of Winds will truly blow your hair back.

Spain has Gran Canaria. The States? Fire Island. And if you crave a gay island escape in Thailand you’ll head for Phuket. But when in Greece (one of the first places on Earth to embrace homosexuality – way back in the 7th century BCE), a modern Mary should set sail for Mykonos. As it happens, we’ll soon visit on our Aegean Sea Gay Cruise. Read on to find out why you’ll love this gay-friendly Cycladic island that’s become an LGBTQ+ hotspot fit for the gods.

Behold Jackie O: the patron gay saint of Mykonos

Until the mid-century, Mykonos was a quiet place where locals made a modest living fishing. Then Jacquline Bouvier Kennedy Onassis – America’s former first lady aka Jackie O – paid the island a visit, and this iconic destination was born.

Initially, there were laid back but adventurous bohemian crowds that came for the beaches. Then once the likes of Grace Kelly, Sophia Loren, and Brigitte Bardot joined Jackie, the rich and fabulous followed. And, to our benefit, the island began to cater to the gay and gay-friendly travellers amongst them. Today, Mykonos rivals European hotspots like Saint Tropez and Ibiza. And it’s all packed into a compact 33 mi2 / 85.6 km2.

But back to that patron saint. If you want to pay tribute to Jackie, she is memorialized by a chain of gay establishments named in her honour: JackieO’. There’s the Bar in Mykonos Town for cocktails and drag shows, the Beach Club at Super Paradise Beach where you can rent private cabanas or dine at the restaurant, and their two latest ventures: the Cantina restaurant, and the Yacht Club – which is actually a disco club – that plays host to famous DJs. Both are located next to the original bar.

Cycladic Architecture

When people picture Greek islands, they conjure up visions of whitewashed homes with thick walls, curved arches, and azure blue accents nestled into steep craggy hills. This is the quintessential style of Cyclades, a group of about 220 islands that include Mykonos. That distinct pair of colours, however, is a relatively recent establishment. It was Greek PM Ioannis Metaxas who declared in 1936 that these two colours be used to represent the white foam of the Aegean Sea against a blue sky. Prior to that, homes were neither plastered nor whitewashed, which allowed them to blend into their surroundings (and served as a form of defence from pirate raids in medieval times).

Along with the homes, windmills were another distinct part of Cycladic architecture. They were originally built by the Venetians in the 1600s, and remained in use until the mid-1900s. But 16 of them remain on the island and we’ll get to pay them a visit.

Old School Charm

Unlike some of the other epic island destinations we’ve mentioned, what sets Mykonos apart is how it’s managed to retain its rustic charm. Mykonos Town, colloquially known as Chora (which translates to town), feels more like an old village than a modern hotspot. Cars are limited, making it a pedestrian’s paradise. It’s still full of old Greek Orthodox Christian locals, but Yia-Yia Bessy won’t bat an eye if you and your honey-bunny saunter by holding hands and/or sucking face like it’s sweet baklava. They all recognize and appreciate that gay tourists helped make their island the affluent paradise it is today.

If you’re craving something a bit more dynamic, consider Little Venice, which emerged in the 13th century. It’s romantic but lively, with many seaside bars and decadent discos.


What good is an island holiday without a beach? Well, Mykonos has over 30 beaches. Some are massive with DJs spinning tunes. Some are discrete and modest. Some are nude. Some are gay. And some of the most salacious ones are nude *and* gay (insert evil grin).

Elia – the longest beach on the island – and Super Paradise are the two we’d recommend for a perfectly gay old time. Full disclosure: Super Paradise has recently become more mainstream (with the exception of JackieO’s), so most LGBTQ+ folks go to Elia, which is more affordable and, well… more gay.


If you just want to park it on a beach lounger and let the day go by, do *not* let us stop you. But if you’re a culture vulture or history ho, join our 2-hour walking tour of the town. We’ll visit Paraportiani church, the castle ruins, Little Venice, the Alefkandra area, and stroll the narrow streets of Matoyiannia.

If you’re interested in venturing off the island, join our excursion to UNESCO-listed Delos (birthplace of Greek God Apollo). This teeny isle, like the majority of the Cyclades, is uninhabited (and a quick ferry ride away). You’ll get to see Hellenistic houses, the Sanctuary (Apollo’s temple), and the guardians of the Sacred Lake: five marble lions from the 7th century BC. Finally, we’ll visit the Theatre and the Roman quarter, where Dionysus’ ancient statues await.

Peak Season Pageantry

We’ll spend two leisurely days on Mykonos in early September. The weather will be reasonable but the crowds remain lively. If you were to book a hotel on the island, you could easily drop $1000/night for a modest room. Instead, we’ll drop anchor so you can relish everything about the island before retreating to our exclusive, exquisite yacht like Stefano Gabbana – of Dolce & Gabbana – who is known to visit and slumber aboard his own luxe vessel.

Has the notion of this gay island stopover aboard our largest cruise to date tickled your souvlaki? Let us know if you have questions, or if you’re ready to book your trip!

By using our website, you agree to the Out Adventures Privacy Policy which includes Out Adventures' practices regarding personal data and cookies.    I AGREE