Our Definitive Guide to the Lesser-Known Greek Island Favored by the Fashion Crowd

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When I was traveling through Greece last summer, there was a single island everyone I encountered was talking about. They were either just coming from it, heading there next, or considering a visit, and it had me seriously considering extending my trip just to see what all the chatter was about. Milos is the Cycladic island that enjoyed an under-the-radar reputation for decades, but amid a post-pandemic travel boom, it's undeniably having a moment.

In case you were unaware, there are more than 6000 islands that make up Grecian territory. Only 227 of these are inhabited, which is still an arresting figure to confront as a casual tourist. For many, a trip to Greece is a once-in-a-lifetime ordeal (even getting there from the U.S. can often be a multiday journey), so choosing the right island to visit is no small feat. There are the well-known choices—Santorini and Mykonos—but for those looking to branch out, it can feel impossible to know where to go.

Milos is a visual feast of rocky white cliffs set against the most brilliant crystal-blue water. Its otherworldly beaches and colorful fishing villages are the main draws, and over the past several years, it's seen a steady uptick in international travel, especially with Americans. What sets Milos apart from nearby Paros and Naxos is its truly remote feel. There isn't one town that everyone flocks to at the same time. Without one central village, the island is more spread out. Yes, this means that you'll probably need a car, but also, even in the height of its travel season in July and August, it rarely feels overcrowded. "There is a lot of range there," explains Yolo Journal founder Yolanda Edwards. "You can go high-end on the hotel and restaurant scene or more middle, and you'll also see a backpacker here and there. I find it so refreshing in that way."

"A few years ago, Milos featured prominently in an ad campaign for Louis Vuitton and was cited as the inspiration for Dior's cruise collection," notes luxury travel consultant Rebecca Bullen. "While the secret is out, it still remains far more chill and cruisey (pun intended) than Santorini or even Paros."

Who What Wear Travels Tip: According to Edwards, mid-September until late October is the time to visit. The sea is warm, and the crowds are gone.

"Compared to the very touristed islands of Mykonos and Santorini, yes, Milos is more up-and-coming," Edwards continues. "But consider that Mykonos and Santorini also became famous over decades when the only way to hear about them was through magazine articles or word of mouth. Milos, Paros—they are quickly becoming very well-known because of the power of social media."

In fact, part of what makes Milos so charming and intimate is its lack of major hotel chains. Instead, you'll find an array of boutique accommodations that range from a private stay in one of the converted waterfront fishing huts the island is known for to a luxury villa that sits atop a seaside cliff. Angela Fink, a Los Angeles–based content creator, chose to renew her vows in Milos last summer. "I was mesmerized by the surreal white volcanic rocks shaped in incredible forms, resembling a landscape from another world," she muses. "At that moment, I knew, without a doubt, that this was the place."

Who What Wear Travels Tip: If deciding between the ferry and flight to transfer between Athens, go for the flight. "The ferry is hot and chaotic," photographer and National Geographic contributor Jessica Sample warns. "The flight is, too, but it's shorter and easier."

Skinopi Lodge is just seven stone villas nestled into the craggy landscape of the island with a footprint so discreet you would be forgiven for forgetting the buildings are there. It is the passion project and brainchild of Nausika Georgiadou, who spent over a decade mindfully bringing Skinopi to life. "The villas are über-minimalist, and the lines between indoor and outdoor blurred. The décor is minimalist so as not to compete with the natural beauty of it all. There are no TVs, and even lighting has been kept to a minimum to minimize light pollution," Bullen says. Skinopi is strategically positioned to face Milos's epic sunsets and maximize the northern breezes that have long been relied upon to cool down spaces. "As Milos becomes a well-known island and tourism increases, these values will become even more rare and important," Georgiadou adds.

Going upscale here means booking a suite at Domes White Coast, a design-forward stay that encapsulates Grecian luxury. Its boho rattan furnishings and sleek infinity pools are set against clean-looking, whitewashed buildings. "It's maybe the most expensive and high-end option on the island," informs Sample. She also gushes that the private plunge pools are dreamy, the sunsets are spectacular, and the service is top-notch. "The restaurant felt fussy and deserted for dinner, but the included breakfast was great," she continues. "Overall, a fantastic location."

Terra Mare Suites is another stay I heard repeated throughout all the recommendations I sifted through. "We didn't stay here, but I wish we had if it had been available," says Sample. "[It's] a white-and-blue fishing house on a secluded cove of turquoise clear water with a little patio. There are so many nearby bakeries to stock up for breakfast, and it's near lots of towns for lunch or dinner. It's also 10 to 15 minutes from the famous white cliffs."

More stays to jot down: For a truly unique experience, rent one of the converted fishing huts Milos is known for on platforms like Airbnb. Bullen also suggests Melian Boutique Hotel and Spa, a property of 15 whitewashed suites that she says showcase the best of traditional Cycladic design. Milos Breeze Hotel is a wonderful boutique option in Pollonia.

If there's one thing I learned about Milos, it's that nobody leaves the island without a meal or two at O! Hamos! The bistro is serving up traditional Greek dishes like horiatiki salad and grilled halloumi, and the move is to order a bunch of small plates to share. From the handwritten menus to the terra-cotta dishware, it's filled with plenty of traditional Greek charm, which Edwards echoes. "It's incredible—everything is from the owners' garden. It's also popular, so go for early or late lunch," she suggests.

Edwards also mentions the recently opened Okto, which is run by a local Greek chef. "Nikos had worked in Paris kitchens for many years and returned here several years ago, bringing a farm-to-table approach," she explains. Expect an elevated take on classic Greek dishes using local and in-season produce. Another plus? It's open from breakfast until dinner. Sample says to request a table in the courtyard and not inside or on the side patio.

Who What Wear Travels Tip: Greek wines, often the cheapest option, are not to be missed here. They're harder to find at home in the U.S., so make the most of trying the local varieties, especially the whites and rosés.

For Fink, Medusa was a dining highlight, where its fresh octopus is dried out in the sun a few steps away from the restaurant. Incredibly fresh seafood is one of the treasures that comes with a trip to Milos, and from what I gleaned, Medusa is one of the top places on the island to enjoy it. Sample echoes her love for the Milos favorite and its legendary seaside location in the charming fishing town of Mandrakia, highlighting that the swordfish souvlaki and cured white anchovies were menu standouts. "They don't take reservations, so [it's] best to queue up at noon and get your name on the list while you wander in the village," she adds.

More restaurants to jot down: Edwards also recommends Astakas in Klima for the perfect sunset dinner on the beach and Emborious Tavern, where you can always get a table without a reservation. Georgiadou is a fan of To Kyma in Kimolos, and Utopia Cafe in Plaka is the undisputed place to be at sunset, says Bullen.

With its swath of otherworldly rock formations, Sarakiniko is the must-see item for any Milos itinerary, and for many photographers and creatives, it's not only a stop along the way—it's the main attraction. Our experts describe exploring the sculpted volcanic rock at this beach (if you can call it a "beach") as stepping foot on Mars. While it does tend to garner a crowd during peak sun when beachgoers line up to jump off one of the cliffs into the glimmering Aegean Sea below, many tell me that they returned at sunrise for a serene and visually striking experience.

Who What Wear Travels Tip: The consensus is to wake up before dawn and watch the sunrise at Sarakiniko before the crowds descend.

Firopotamos isn't so much a beach as it is an "enchanting little cove," as Fink puts it. While there is a sandy beach, it's also a quaint seaside town with old ruins. You'll want to dock a boat here and dive into the water, but she ensures that you can drive there as well. "The water is perfection," Sample adds.

Even though Kleftiko is more of a dramatic rock formation than a traditional beach, it was hard not to feature it, as it ranks high on everyone's list for the top swimming spots around the island. Charter a boat for the day—Sample recommends hiring Excellent Yachting for a full-day cruise from Adamas port—and stop here to snorkel and swim through the stunning sea caves.

More beaches to jot down: There are many wild beaches that you can have to yourself, Edwards informs. She's a fan of Kastanas and Fyriplaka. There are also plenty of organized beaches, such as Plathiena, which has umbrellas, loungers, and a taverna.

While Pollonia and Plaka are the two most upscale towns and where you'll likely find yourself dining and shopping the most, Klima is a must-visit. The picturesque fishing village is a former fisherman's village where you'll find colorful homes nestled along the water's edge, many of which have been converted into Airbnbs that make for a very unique stay.

Built by the Venetians who ruled Milos, the castle that is now a Greek church is on the second-highest peak on the island, making for an epic sunset view.

Who What Wear Travels Tip: Renting a car is a must here, as everything is spread out. Prioritize an SUV or four-wheeler that can best navigate the rocky terrain.

One of Georgiadou's favorite things to do when she's not running things over at Skinopi Lodge is to hike through the ancient city—which is close to her resort—past the ancient theatre and the catacombs, and on to the sea.

More sights to jot down: Edwards suggests a hike up to Nychia, the ancient obsidian quarry with incredible views that is accessible via footpaths surrounded by wild thyme. She also mentions Pollonia, the more upscale town that always has a new restaurant or store every season. Fink suggests planning a visit to the Marmara Sand Museum "if you are a rock nerd like [her]."

The general consensus is that a Milos-bound suitcase should adhere to the standard island wardrobe rules: light, airy layers that can withstand the heat coupled with practical but beachy accessories that you can pair with any number of outfits. "A hat that ties under the chin is a must!" Edwards insists. "Whether you're hiking, sitting on the beach, or taking a boat trip, the wind can kick up, and you'll thank me that you had yours tied down."

Footwear should be minimal but walkable—a pair of rubber flip-flops won't cut it here. Instead, you'll want to opt for sandals with a substantial sole that can keep up with all the rocky beaches you'll be exploring, like the Chanel Dad Sandals that Fink relied on for her trip. Since nightlife here translates to an evening dinner overlooking the Aegean, you can skip the party attire and focus on easy, elevated ensembles like airy linen and silk dresses. The main event of your suitcase should, naturally, be swimwear along with cover-ups and SPF-adjacent accessories, like a good sunhat.