The Greek Island That Makes You Feel Like a Chic Traveler 1

Every year countless thousands of us sit down in front of our computers and frantically try to figure out which Greek island to go to. Just going to Santorini and Mykonos would seem too basic—or we’ve already been and want to feel like we’re going somewhere a traveler and not a mere tourist would go.

In May, with Greece open and few tourists likely until June, I wanted to see those Santorini sunsets without the crush of tourists. Something about all the Instagrammers I saw at Sarakiniko on Milos made it less appealing, and while Folegandros seemed like a good fit, the person I was traveling with had already been. Paros and Naxos looked cool, but something just wasn’t right for me.

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So, I took the advice of a Greek friend and opted for an island that had everything I wanted—charm, natural beauty, great food, and just enough difficulty to weed out mass tourism.

The island of Sifnos.

Sifnos has no airport, so it’s by boat that you’ll get to this mid-sized Cycladic island. The port of entry is Kamares, a lovely harbor with a long stretch of beach and a mountain rising behind it. It’s made up of delightful white buildings with blue shutters, a number of which you can sit at and order a frappe coffee, the Greek-style iced coffee that was trending on Tik Tok early in the pandemic because it’s made with instant coffee. (I’m more of a double espresso guy so I was a little skeptical, especially because of the sugar, but I loved it, especially after the three-hour ferry from Santorini.)

You arrive at Kamares, the port village, where you will be greeted with sight of the lovely harbor. A car on this little island is a must, and there are many rental services at the port to make it easy. Generally speaking, I know nothing about cars, but I would advise getting a car with good clearance off the road. The Honda Civic we rented was clearly not the best choice (it was the only automatic car they had available). There are a lot of rough little roads to get to different beaches and pretty spots on the island. In addition to knowing next to nothing about cars, I also have a terrible sense of direction, but everything is about 25 minutes from the port and navigating the island is straightforward.

In addition to finding the ideal island, don’t we all also crave that iconic Greek stay with dramatic views of the Mediterranean (the Mama Mia fantasy). And on Sifnos I found what is unequivocally my favorite AirBnB I’ve rented—ever.

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Villa Fengaria is a little paradise set at the edge of the island down a bumpy road (extra reminder about that car selection!). The host is Ella, a half-French half-Greek woman who designed the whole estate. It’s very much a mix between a south of France summer house and the traditional Greek white house. (From July through August, Ella told me, Parisians occupy every little corner of the island.)

The sweeping views that transformed every night at sunset into a polychromatic sky followed by exceptionally bright stars with almost no light pollution except from the island miles away meant I felt no need to leave to go out to dinner. Instead I preferred cooking a simple meal with ingredients from the market nearby. After an amazing but touristy stay in Santorini, this semi-remote villa on Sifnos was refreshing.

But if I turned into a homebody, that did not mean there was nothing to do on Sifnos.

Beautiful white stucco churches with blue domes are not rare on Greek islands, but the Chapel of the Seven Martyrs on Sifnos is special. It’s perched on an islet jutting out from Kastro, the island’s ancient capital. Unsurprisingly, with the blue of the Mediterranean contrasting with the white chapel in such a dramatic setting, it’s the most photographed spot in Sifnos.

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But the best part about this place is not the chapel but the cliff by its side where you can swim and jump. It was only when we got there and saw a group of teenage girls and boys on top of the rocks that we realized we could go in. We didn’t have our suits, but, luckily this was Europe so nobody was shocked by us going in in briefs.

It was like a scene out of a film—a group of teenage girls and boys lounging on the rocks daring each other to jump in the clear water.

One of Sifnos’ more iconic beaches is Vroulidia—one of those classic Mediterranean spots that’s tucked in a cove and surrounded by cliffs. However, if you are a fan of sandy beaches, this one is not for you as it’s also a classic Mediterranean pebble beach.

Vroulidia is supposedly accessible by car, but this really wasn’t the case for us considering, again, the car we rented. So we parked a 20-minute walk away. Usually this wouldn’t be a problem for me, but I had the less-than-brilliant idea to wear leather sandals, a nightmare for this rocky steep walk. But I got very lucky: a car stopped and offered to bring us down.

I always worry when restaurants have great views because I fear they’re selling scenery more than food. But at Taverna Chrisopigi, everything was fantastic.

The two Frenchmen who gave us a lift were renting a villa nearby and were surprised to hear that we were trying to get to this beach. We soon realized why: The two taverns where you might normally rent sandals and parasols were completely closed! Wooden piers that are usually there to ease the access to the water were also removed. The beach was completely deserted (except for the two men who helped us). A little disappointed, we ended up finding a concrete dock on the side of the creek perfect to lay on and jump off into the water. I imagine that once tourism returns full time, the amenities will also come back. While my sartorial choices were poorly planned, I did manage to pack bread, cheese, and water (a godsend, because the walk back to the car was even more brutal).

Out of the few times we went out for lunch, my favorite was Taverna Chrisopigi. It’s right by the beach of Apokofto, a small but sandy beach with crystal clear water. I always worry when restaurants have great views because I fear they’re selling scenery more than food. But at Taverna Chrisopigi, everything—the seafood, the lamb, fried tomatoes, and stuffed eggplant—was fantastic.

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Before you get on your ferry to return to Athens, or another island, take a final swim at Faros Beach right by the port. If you want to make the moment last into your ferry ride, grab a gyro on one of the terraces to take with you.

COVID-related info: We entered Greece in the first week that all its internal restrictions were lifted. Getting in was easy with the vaccination card and test taken less than 72 hours before arriving. One thing to keep in mind, however, is that depending on the place you are connecting you might need a test that was taken 48 hours before arriving at that airport (like Munich), though more direct flights are opening up later this summer.