Finally, and this is perhaps the best tip of all – as it’s the old-style romantic one – book transport to and accommodation on one starter island (Paros is a good choice). Sail/fly there, sit down relax, pour cold drinks and eat healthy Greek foods for 4-5 days while working out where to go to next with your tablet under an umbrella on the beach. Book your next stop online and go there. Repeat the exercise. No hassles about being locked into a fixed itinerary and if you like a place, you stay longer. If not, you move on. You will generally find transport tickets for a day or three ahead and hotel owners often know someone on the next island who can fit you in. In Paros, Petres Hotel is a good starting point. Good luck and happy sailing!
Ferries between Naxos and Milos don’t start until June 7th (one each way, every day after that). Ferries between Santorini and Milos start April 28th and there is one every day in each direction. And there are always ferries between Naxos and Santorini. So if the dates work I would fly to Santorini (the longest leg) then ferry to Milos then Naxos and back to Athens. But if you need to travel between Naxos and Milos before the 7th then ferry Athens to Milos to Santorini to Naxos and back to Athens.
Mykonos had gay clubs and sunrise parties long before rave culture was even invented. Its bohemian allure hasn’t faded since the 1960s, although the once naked beaches now have nail bars, personal trainers and house music pumping out all hours. The influx of supermodels and superyachts has inspired hot new hotels and restaurants. The hippest place to show off your abs is Scorpios, a louche beach bar that puts Ibiza's finest in the shade (book a cabana to watch the sunset). After hours, it's always Astra, where you might find Keith Richards chatting up Karolina Kurkova. The gay crowd has dwindled, but drag queens and oiled bodybuilders make a splash at Jackie O, overlooking Super Paradise bay.
Where to stay in Corfu: Rou Estate a hilltop hamlet transformed into a five-star retreat with an excellent spa. CV Villas has cornered the market in covetable villas on the north-east coast of Corfu. If you’d rather go all-inclusive, check into the smart Ikos Dassia, which opened in May 2018 in Dassia, a favourite haunt of The Durrells cast and crew. Guest perks include a Mini Cooper for cruising around the island.
The almighty church has kept nightlife in check. If you must see and be seen, head to quietly glamorous Astivi or Stoa bar, on miniature Agia Lesvias square, in Hora. Beach life is generally languid and low-key; Psili Ammos and Livadi Geranou are our favourite hideouts. Dinner reservations are essential at Benetos, for Med-Asian fusion on an organic farm, and Lambi for grilled fish on a purple pebble beach.