Greece’s lesser-known Cyclades islands are made for hopping

Secluded coves with emerald waters and dramatic rock formations await the curious traveler willing to venture off the typical island itinerary.

The town of Oia, on Santorini.Jorg Greuel/Getty Images/Getty Images

A traveler could spend a lifetime exploring the 200 or so inhabited Greek islands that stretch across the Mediterranean, Aegean, and Ionian seas, and it would be hard to argue that this was not a life well spent. All fly the same blue-and-white-striped Greek flag, but each has its own history, landscape, and personality, shaped over centuries by, among other things, nature, trade, and the architectural tastes of visitors and occupiers. Yet many visitors venture only as far as two of the best-known islands: Santorini and Mykonos.

My advice? Don’t skip them — they’re popular for a reason — but make a visit part of a trip that includes two or three lesser-known islands. Link them with ferry rides or short flights, and you’ll have a journey jammed with beaches of your dreams, small and accessible ancient sites, simple food, and real hospitality. You’ll find no high-rise Hyatts on these islands, but lots of small hotels and tourist apartments. Many will be family-owned or small businesses, with proprietors who seem genuinely glad to see you. July and August are peak season, but when we travel in late May, most places are open, with uncrowded beaches and water warm enough for swimming.

Island hopping takes planning, and at first, the sheer number of choices can make it overwhelming. But it’s also an education in itself and, for me, part of the fun of traveling to Greece. Relying on a good ferry network and easy connections from Athens, my husband and I settle on the Cyclades, a group of islands southeast of the mainland. We plan to spend two weeks on four islands — Sifnos, Milos, Santorini, and Naxos — and the trip proves to be just the right mix of travel and staying put.

We begin our travels in Sifnos, a petite charmer of an island, where the first things we notice on the drive out of the port town of Kamares are the stone walls. Some seem absolutely ancient, others of a more recent vintage. They’re everywhere: running up and down through the hills and stitching together groves of olive trees, hayfields, and pastures, where the bells of roaming goats clang in the breeze.

The next thing we focus on is the distinctive Cyclades architecture and color scheme: low-slung, cube-shaped houses, whitewashed and bright blue trimmed, except for the occasional rogue with green or red doors. Sifnos is famous for its traditional pottery and its multitude of blue-domed churches and monasteries, which appear around nearly every curve and atop every hill, tucked into narrow valleys and at the tip of rocky promontories, like the stunning white monastery of Chrysopigi. And did I mention the cats? They are everywhere, too, so many that they have their own website: feedsifnoscats.com.

Like most islands, Sifnos offers a range of accommodations, from apartment colonies in the beach resort town of Vathi to guesthouses in the hilltop island center of Apollonia. Many visitors stay in Kamares, which has a long, sandy beach lined with restaurants and cafés. We fall in love with the tiny fishing village of Faros, where accommodations at Thalatta studio apartments (sifnosthalatta.gr/en/) perch on the water’s edge. Clean and spacious, the apartments are located an easy stroll from the Glyfa and Fassolou beaches, and several tavernas along the waterfront. There’s also a well-marked system of hiking trails that allow you to explore the island on your own, or with a group, through Hiking Sifnos (sifnoshiking.com).

Stone walls dot the landscape on Sifnos. b.j. roche

One day we drive up to the village of Cheronissos for lunch and a swim in its picture-perfect harbor. The next, while exploring the island’s old capital of Kastro, a walled village that sits overlooking the sea, we meet expat Christian Brechneff, a 68-year-old painter and writer who first came to the island as a 21-year-old artist, looking for a place where he could paint without distractions. His memoir of that time, The Greek House, details a more insular, less developed Sifnos of the 1970s; he is back showing a friend his old stomping grounds, and he lets us in on his tour: “Right here is where I got into a fight with the post office over a stamp!” he says with a laugh, pointing to a small blue doorway that is now part of a private home.

To the locals, Brechneff and his friends were oddities back then, but these days you might hear nearly as much French being spoken as Greek. Still, some things are the same. In nearby Apollonia, we munch on cheese pies and watch the people go by. Here you buy a small trinket in a shop and the proprietor wraps it in paper as if he’s at the counter at Tiffany.

The next morning, a 40-minute ferry ride brings us to Milos, a larger, volcanic island with a coastline marked by more than 75 beaches, many of which are accessible only by boat or ATV. We have two rooms, a patio, and a full kitchen at our apartment at Vivere a Plakes (viveraplakes.gr), a short walk from Plaka, the island’s hilltop capital. But we’re happier chowing down on stuffed peppers and tabouli salad at the colorful open-air neighborhood joint, Fatses (facebook.com/milofatses), next to the ArchaeologicalMuseum of Milos.

We drive along the northern coast to Sarakiniko, where a tiny sandy beach is tucked in between the real attractions: dramatic white rock formations that dip and swirl and hollow out as they meet the deep blue of the water. It’s too windy to swim, but scores of visitors are sunbathing and scrambling over the rocks, like us, mesmerized by the views and the strangeness of the landscape.

Really, the best way to see the beaches and coastline of Milos is by sailboat. At Horizon Yachts (horizonyachts.gr) on the Adamas waterfront, we join a group of Irish twentysomethings for a daylong trip that includes lunch, drinks, and lots of swimming. After about a half-hour sail, we reach the island’s other jewel, Kleftiko. And here it is, the peak swim spot of this trip: a secluded cove with emerald waters so clear you can see the ocean bottom. The boat captain takes a smaller group into a pirate cave on an inflatable dinghy, but we’re content to swim around the other caves and volcanic rock arches that jut up out of the water. Bliss.

Sarakiniko beach on the island of Milos. brad geddes

For history lovers, Milos offers some archaeological sites worth exploring. The ancient theater of Milos, for example, is a partially excavated Roman theater that sits on a bluff with a breathtaking view of the sea. Not far from here, Venus de Milo, the island’s most famous “expat,” was unearthed by a farmer in 1820 and later shipped to the Louvre.

Also not to be missed is the village of Klima, home to colorful two-story syrmata — fishermen’s boathouses that line the water. If you’re charmed enough, you can even rent one on Airbnb (airbnb.com/s/Klima -Greece).

“We’ve made a mistake!” I think as our ferry unloads at the crowded port of Santorini. Unlike the ports at Sifnos and Milos, this one is designed to move thousands of people as quickly as possible. Offshore, a pair of enormous cruise ships languish like an invading force before the onslaught, and around us, hordes of buses growl, waiting to take the newcomers up the switchback road to the town of Fira.

Fishermen’s boathouses in the village of Klima. brad geddes

When mapping out this trip, I wanted to avoid any place with cruise ships; the original plan was to connect to the afternoon ferry to Naxos after a quick look around Santorini (the only island where we didn’t rent a car). But a sporadic spring ferry schedule has marooned us here for two nights.

After settling into our studio apartment at Maria’s Place (mariasantorini.com) on the outskirts of the tourist town of Oia, we walk up to the stone-paved cliffside path that winds along the coast, and that’s when we see it: the nearly submerged and stunning caldera of Santorini, which sits like a giant blue pool bounded by the island’s rocky landmass. Stretching as far as you can see, this view is so wide, so deep that it brings to mind the Grand Canyon. Whitewashed cave houses, cut from the soft volcanic rock, drape the coastline, their swimming pools shining like shards of lapis-colored stained glass in the early evening light.

It was then that I realized how stupid I had been: sure, it’s packed. But to skip Santorini and miss this incredible view would have been a big mistake.

The next day we take a bus to Akrotiri, a Minoan city buried under volcanic ash from an eruption in the 17th century. It was first discovered in 1866 by miners digging for volcanic earth for use in the construction of the Suez Canal. While only a small portion is visible now, the site is among the most extensive in the Cyclades. The ruins are enclosed in a shaded canopy and offer a glimpse of everyday life more than 3,500 years ago. Later, at the Museum of Prehistoric Thera (santorini.com/museums) in Fira, we get a close-up look at the wall paintings, ceramics, and other finds from this historic site.

Island tip: Always carry your swimsuit and towel, no matter where you’re going. From Akrotiri, we stroll down to the water and hear the call of the water taxi: “Red Beach! White Beach! Black Beach!” We choose the mountain path over to Red Beach, named for its dramatic red dirt cliffs. There we cool off amid a troupe of 10-year-old Italian schoolboys on vacation.

From Santorini to Naxos, we use Blue Star Ferries, which has several open-air decks, food vendors, and lots of space to spread out. Ferry life is part of the trip, and now we are old hands. We stand on the deck and watch the black coast of Santorini disappear, and, for a few hours, we’re down to the elements: sun, sky, and sea. There are faster ways to get around, but they certainly aren’t as much fun.

Naxos is the largest island in the Cyclades, with the most agricultural landscape. We disembark at Naxos Town, on the western shore, and check into Iliada Studios (iliadastudios.gr), which overlooks the sea. From our patio, we have a ringside view of the island’s iconic half-finished Temple of Apollo, known as the Portara, or doorway. We can’t believe our good fortune.

The ancient Temple of Apollo, known as the Portara, or doorway, on the island of Naxos. adobe stock

The next day, we drive inland, and after a few miles, we’re in the middle of the most gorgeous rural landscapes — terraced rows of olive trees, golden hayfields, and a small white village, all enclosed by the mountains where, it’s been said, Zeus grew up. Near Sangri, we explore the tiny ruins of the Temple of Demeter, the goddess of agriculture and fertility of the earth, which dates back to the sixth century BC. Then it’s on to the village of Halki, where we have a Sunday lunch of rotisserie grilled chicken and sausages under a lush shaded canopy of grapevines at Giannis Tavern.

That evening, back in Naxos Town, just as in Santorini, a crowd makes its way to watch the sunset — only here, they parade out to the Portara and sit on the rocks as the light fades.

On our final morning in Naxos, we explore the Venetian Castle, a fortress of whitewashed stone pathways that meander past galleries, shops, and small cafés. We follow the sound of a jazz guitar back to its source; it’s Nikos Giolias, a jazz guitarist from Athens, practicing for a concert that evening at the Domus Festival, a cultural event in the complex that offers movies and concerts. The manager invites us to the show that night. We tell him, with regret, that we have a ferry to catch.

But, we assure him, we’ll be back.

> IF YOU GO

Ruins of the Temple of Demeter on Naxos.adobe stock

Fantasy Travel offers an excellent DIY trip planner that lets you explore the islands and create your own trip (fantasytravelofgreece.com).

Two other great resources are Matt Barrett’s greektravel.com and his Greece Travel Guides Facebook group. Barrett, a Greek-American, started his site in 1996, and though it still has an old-school look, the information is invaluable.

Plan to spend at least three or four nights per destination, and remember that travel between islands can take a day.

Different ferry companies serve different sets of islands, which can complicate travel planning. Ferryhopper.com aggregates schedules and lets you buy tickets from different companies. (Summer ferry schedules are already out.) Beware that buying ahead locks you in, and ticket refunds can get complicated. If you’re changing plans, do it as far in advance as possible.