It’s almost as much of a cliché as breaking plates at a tourist trap of a taverna: trying to stuff as many islands as you can into a Greek holiday. But 2020 saw the swift demise of that particular vacation playbook.
The new mantra to swear by? Less equals more. It’s about quenching your thirst for discovery while dialing back on the logistics a bit, the better to savor the flavor of a place. Think less mad rush for the next ferry, and more meaningful experiences instead.
So, enter perfect island pairings. Like earrings, one island can dazzle and delight, but don’t they often sparkle brighter as a set?
Santorini + Ios
The most instantly recognizable Greek island hardly needs an introduction; in terms of scenery and tourist attractions, Santorini is in a class of its own. The small island was on the verge of becoming too popular, but that was before the pandemic. Go there now and you can expect a calmer experience overall, at least for a while.
But, for all its unique heritage and spectacular caldera views, there are two things Santorini never had: a roomy interior or truly stupendous beaches. You will, however, find both those features just 21 nautical miles to the north, on the island of Ios.
Ios is less Instagram-friendly than its famous neighbor to the south, but it is wonderfully Cycladic in myriad other ways. Wide beaches of golden sand, such as Mylopotas, rock a youthful vibe, while Manganari, at the southern tip of the island, pretty much spells Aegean Sea bliss.
In between, there’s a lot of arid, natural landscapes, and driving through them is a Zen-like experience. When you’ve had your fill of calm, shake things up a bit in Hora, the island’s capital, stacked up on a hill above the little harbor.
Milos + Kimolos
Milos is another volcanic island in the Cycladic chain and, though it’s been gaining in popularity with international visitors in recent years, it still tends to be better known among Greeks. The white lunar landscapes of Sarakiniko get a lot of mileage on Instagram and the ribbon of scenic beaches around island—where the famous Venus de Milo is from—doesn’t disappoint, either.
A glance at the map reveals the presence of an islet northwest of Milos called Antimilos, but that’s only home to a colony of rare wild goats, so not the ideal island pairing.
What you want is Kimolos, a more rustic island just to the northeast. Known for its mineral riches in antiquity, low-key Kimolos hits all the Greek island high notes—whitewashed Cycladic architecture, a fine assortment of uncrowded beaches and even some archaeological intrigue.
Paros + Antiparos
As Greek islands go, Paros almost has it all: a bustling main port, Parikia; breezy Naoussa in the north; attractive villages; and great beaches like Kolymbithres and Golden Beach (great for windsurfing).
While Paros isn’t small at all, and there are plenty of places to slow down and chill, for more of a getaway feel it’s worth taking the ten-minute ferry to neighboring Antiparos, and staying for a few days there, too. Definitely come with your rental car if you have one.
Long considered an insider’s island with plenty of discreetly luxurious bolt-holes (many private), Antiparos offers rugged landscapes, a famous cave you can visit and very good beaches that invite endless summer idylls.
Mykonos + Syros
Mykonos is a one and only kind of place, so any pairing with it that you might have in mind is strictly going to be in the interest of island diversity and inclusion, so to speak.
I suggest coupling it up with Syros, because the two islands are almost polar opposites, despite the fact that only a 45-minute ferry ride separates them.
Mykonos is as much a state of mind as an actual place, and something to be experienced at least once. Syros, on the other hand, is very real. Its harbor town of Ermoupoli is a rather perplexing sight when you first glimpse it from the boat as you pull into port. It bears none of the features that make up the classic Cycladic look at all, but, upon closer inspection, it reveals itself to be rich in history, complex in texture and full of cosmopolitan energy.
And there’s much more to the island than just Ermoupoli; Syros packs in plenty of places worth exploring.
Rhodes + Symi
In the movie “Pascali’s Island,” a 1980s drama starring Ben Kingsley and Helen Mirren, the setting was a fictitious island that resembled a hybrid of Symi and Rhodes and was, in fact, filmed on both; Symi’s distinctive 19th-century harbor-front clock tower makes several appearances in the film.
With its stunning medieval architecture, ancient ruins and myriad beaches, Rhodes is undoubtedly an all-time Greek classic; and just 39 km to the north, Symi is very much a small-gem island temptation. The old neoclassical houses with their elegant facades and red-tiled roofs make the main harbor and onetime sponge fishing center, Gialos, a photogenic standout in the Dodecanese, while elsewhere on the island fine beaches like Nanou beckon.
Like Rhodes, Symi exudes historical atmosphere and has a proud nautical tradition, too. The islands are less than an hour apart via high-speed ferry.
Kefalonia + Lefkada
If you like lush green mountains to go with powdery white sand beaches, the Ionian islands and you are probably going to get along famously.
There are far fewer Ionian islands than Aegean ones, which makes it easier to pick your perfect pairing in these parts, and a natural one is Lefkada—actually joined to the mainland by a long causeway—and Kefalonia.
Each island has its fans, and the contest between which one has the best beaches—Lefkada’s Porto Katsiki versus Kefalonia’s Myrtos Beach, for example—may best be resolved by visiting both islands.
The ferry from the port of Nidri in Lefkada to Fiskardo in Kefalonia takes about one hour and 45 minutes.
Tinos + Andros
Andros may seem a little aloof at first, perhaps befitting its distinction as the most northerly of the Cyclades, but, as they say, vive la différence. The main town is on the opposite side of the island from Gavrio, where the ships land, and its stately mansions originally built by wealthy shipowners speak to a proud maritime heritage. And once you happen upon secluded beaches like Achla and Zorkos, you probably won’t want to leave.
This is understandable, but neither will you want to miss out on my suggested pairing here, which is Tinos, the next island south. From the southern tip of Andros, you could probably swim to the northernmost point on Tinos, but don’t. Take the ferry instead. The ride is worth it to discover an island which, like Andros, has fancy dovecotes scattered throughout the countryside (although it has more of them than Andros), better-known beaches and you might say a more classically Cycladic feel.
In the old days, Venetian occupiers tapped into the island’s agricultural potential and, even today, the island is well known for two things: it tends to be very windy, and the food tends to be exceptionally good.
Spetses + Hydra
This pairing delivers both historical importance and classic island appeal relatively close to Athens—and each island has its aficionados. Hydra has a magnificent harbor and genteel charm but relatively few beaches, and donkeys have taken the place of cars—which is great unless you happen to like getting behind the wheel.
Spetses also has no cars, or at least very few, but its landscapes are less austere, with plenty of beaches to choose from. And while, like Hydra, the island had a prominent role in the Greek Revolution—which celebrates its bicentennial this year—some find the overall vibe more relaxed in Spetses, although both have an unmistakably upscale tilt.
Spetses and Hydra are very different, very Greek and very close to one another (the ferry ride is half an hour, tops)—in short, all the right ingredients for another perfect island pairing.