The most common itinerary we are asked for is Athens, Mykonos, Santorini. It is a good trip. It is also the trip everyone else is doing, and after four nights of Mykonos most couples want somewhere that lets them exhale. The second island is where a holiday becomes yours.
Paros and Naxos
The obvious upgrades. Both are big enough to have real towns and real life outside tourism, both have excellent food, long beaches and proper villages inland. Naxos has mountains and the best produce in the Cyclades. Paros has Naoussa, which is the prettiest harbour in the group and busy in August for good reason. Ferries are frequent, so neither costs you a travel day.
Milos
The one everybody has started talking about. A coastline that looks lunar, the white rock at Sarakiniko, and boat days out to sea caves you cannot reach any other way. It is no longer a secret and it is still extraordinary. Go before it becomes the next place people complain about.
Serifos and Folegandros
For couples who genuinely want to disappear. Steep, small, quiet, with hilltop towns that look like the postcard version of Greece without the crowd standing in front of it. The catch is honest: ferry connections are less frequent, so these need planning rather than improvising, and that is precisely what we are for.
And Santorini
There is no gay scene on Santorini worth the name. It is also completely relaxed about two men on honeymoon, and it remains one of the most beautiful places in Europe. Treat it as the romantic half rather than the social half and it does its job perfectly.
The pattern that works, almost every time, is loud then quiet. Mykonos first while you have energy, then somewhere that asks nothing of you. Doing it the other way round is a mistake we see people make once.
More on this in the Gay Greece guide.