The Cyclades, the island group around Santorini and Mykonos, has around thirty islands to choose from, and that's before you look at the rest of Greece.
It's a lovely problem to have, and it's also why an island-hopping plan can so easily grow a little too ambitious.
As the smaller islands start closing for the winter, this is a good moment to start thinking about next year.
If you came into No.82 with Greece on your mind, this is roughly the conversation we'd have with you.
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A little guidance on when to go
May and June are wonderful months for the Greek islands, and so is September.
In May you'll still find the wildflowers out, while June is a little warmer, and if you can aim for the middle to the end of May, the weather tends to be wonderful.
Even Naxos, which is a little busier and more commercial, has plenty of room to breathe at the end of May or the start of June.
July and August are when the wind usually blows across the islands, which matters rather more than you'd think when your plans depend on ferries.
September is beautiful too, with one small piece of geography to keep in mind.
The further north you go, the sooner the weather can turn, sometimes as early as the start of September, so as the month goes on we'd point you further south.
Down there, the good weather can last right up to the end of October.
The catch is that October is when the small islands start winding down for the year, with restaurants and hotels beginning to close, and from around the middle of September the ferry companies start combining sailings and cutting some routes altogether.
So our answer is the middle of May to the end of June, or September.
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Two or three islands is plenty
We know how tempting it is to plan a Greek island trip like a tasting menu, with a little of everything and as many courses as the days will allow.
For a holiday of ten days or so, we'd suggest two or three islands at the most.
Every island has its own character, even ones twenty minutes apart.
You need a little time on each one to notice it, and we find that's where the pleasure is.
On the smaller islands especially, it only takes a couple of days before the faces start to feel familiar and the café you keep wandering back to begins to recognise you.
That's the part of island hopping we love most, and it's the part you miss if you're packing again every other morning.
'Every island has its own character, even ones twenty minutes apart.'
One shape we like is a night or two on Santorini, which is long enough to see the caldera and the ancient town at Akrotiri, preserved under ash from the eruption and now a museum. After that, we'd give you a few nights each on two of the quieter islands to the west.
Most of the boat hops between them are short, which is a big part of why we like this route. Santorini to Folegandros takes around forty-five minutes, Folegandros on to Milos about an hour, and Milos to Sifnos around forty-five minutes again. Going straight from Santorini to Sifnos is longer, at around two and a half hours.
For getting there, Santorini and Mykonos have flights from Gatwick and Heathrow at the moment.
And for getting home, Milos has its own domestic airport. The flight up to Athens takes around half an hour, and from there you fly on to London, collecting your bags and checking in again in Athens because it's a different airline.
One small warning if you're not a confident sailor.
The crossing of around two hours from Sifnos to Naxos is run by the smallest boat on the route, and the small boats are the first to stay in port when the wind picks up. This one also has a couple of nicknames, neither of which we'd repeat over dinner.
If boats aren't your favourite thing, we'd leave that leg out and keep you on the shorter hops.
'That's the part of island hopping we love most, and it's the part you miss if you're packing again every other morning.'
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Why a two-star might be the best hotel you book
Hotel star ratings in Greece work differently from ours.
Greek star ratings go by facilities, not by how a stay feels.
A hotel can miss out on a star because it doesn't have a restaurant, or because it sits ten metres further from the beach than the regulations allow.
Some of the most charming small hotels in Greece are rated two stars and feel like a four-star anywhere else.
We love finding those.
So if a hotel on the shortlist we send you says two or three stars, please don't let that put you off.
The smaller islands have fewer big, top-end hotels in any case, and we rather like that. You'll find more family-run places, and alongside them some beautiful boutique hotels.
All-inclusive tends to stay on the biggest islands, like Crete, Corfu and Rhodes, so on the smaller ones we'd usually look at bed and breakfast instead.
On Folegandros and Sifnos, your hotel will usually collect you from the port, too.
It's a little thing, and a rather lovely one after a morning on a boat.
'Greek star ratings go by facilities, not by how a stay feels.'
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Past Santorini, to the quieter islands in the west
From Santorini, the ferries head two ways, north or west, and the more relaxed islands sit along the western route.
Folegandros is the closest, around forty-five minutes away, and it's known, fittingly, we think, as the island of peace.
It's rugged and traditional, with whitewashed houses and blue shutters, a few nice beaches, some charming small boutique hotels and a good choice of tavernas. The walk to do is the zigzag path up to the church on the hill.
Milos is about an hour further on, and it's where the Venus de Milo was found. There's a museum, and catacombs too, if that appeals to you as much as it does to us.
Its landscape is so moon-like that films set on the moon have been made there, and its beaches are wonderfully different from one another.
Twenty minutes away by boat, with a sailing every hour, is tiny Kimolos, which still has the feel of the islands a generation ago. A few hours wandering there makes a gentle way to spend an afternoon.
Sifnos is known for its food, with a food festival every year, and it has beautiful churches and great beaches.
One of its beaches has protected water so shallow that you can wade out a hundred metres and still be only about waist-deep, which makes for an easy, unhurried swim.
We'd happily send you to any of these three.
If you'd prefer a busier island with more going on, we'd look north to Naxos. It has great beaches, a castle above the town and the Portara, the old doorway to a temple, where the sun sets right through the frame.
Head inland and you can see how kitron, the island's own citrus liqueur, is made, and taste a little before you decide whether a bottle comes home with you.
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Somewhere to start for next year
If next May, June or September is already on your mind, we'd love to help.
Pop into No.82 on Poole Road, call us on 01202 144101 or email hello@agentnouveau.com, and we'll find the little islands that suit you best.
Come find us at No.82.
hello@agentnouveau.com