Greek Island Hopping Is the Low-Key Summer Vacation You've Been Craving

Updated 05/15/18
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There's something about the Greek Islands that always makes travelers come back for more. It's a vacation that seems to evolve and mature as you do. The glitzy nightlife in Mykonos and Ios beckoned in my early 20s, Santorini's romantic caldera was the perfect first trip with my boyfriend, and the quieter bays and world-class cuisine make me want to return now that I crave a more relaxed vacation.

Unlike many destinations, one of the most alluring parts of a trip to Greece is getting around. The Greek archipelago is made up of roughly 6000 islands and islets, of which only 227 are inhabited. So naturally the best way to explore is by boat—either charter your own or book the ferry to jump from island to island until you find one that suits your style. To get you started, here are some of the most beautiful islands I've visited as well as a few I've discovered via word of mouth from friends and travelers. Consider this your go-to Greek Islands guide to eat, sleep, beach, and repeat all summer long.

Zakynthos

Shipwreck Beach, Zakynthos
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The Traveler: Zakynthos is perfect for travelers who prefer activities over lazy beach days. It's best seen from the water, so is ideal for those who love boating and snorkeling. Travel and fashion blogger Jessie Bush goes so far as to say, "If being a Greek island was a competition, then Zakynthos would be awarded the top spot."

The Location: It's located in the Ionian Sea and is a good choice if you don't have time to visit remote islands. Explore the mainland, jump over the Kefalonia, and then continue up the coast to rugged Albania and sparkling Croatia.

The Insider Tip: If you tire of the crowds after visiting breathtaking Shipwreck Bay, Bush recommends changing tactics. "I'd advise to avoid the well-trodden south and head straight up north to find a quaint hotel nestled in one of the villages," she says. "We hired our own little boat to explore the bays and secluded beaches; hands down the best part of our trip."

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Antiparos

Antiparos Travel Guide
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The Traveler: Antiparos is perfect for those who want to vacation with Greek locals, rather than overseas visitors. I first heard about Antiparos during a trip to popular neighboring island, Paros. Locals told me about the stunning beaches and said this is where they escape to in peak season.

The Location: Blink and you'll miss it, Antiparos is a tiny island in the southern Aegean, at the heart of the Cyclades. It's a short boat ride from Paros, making it an easy day trip if you'd prefer to stay on a larger island with more restaurants, shops, and hotels.

The Insider Tip: Stop by Antiparos Cave, an ancient cave system that dates back to the Stone Age. Ancient graffiti adorns the walls, and you can find names and scrawlings written before the birth of Christ (yes, really).

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Milos

Milos Travel Guide
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The Traveler: Prefer to dive off rocks and explore untouched, rugged coastline rather than battle for a patch of sand at the beach? Then Milos is for you. It has great hiking trails and incredible white rock formations that make for the ideal (albeit slightly uncomfortable) lounging spot. Conde Nast Traveler writer Eleni Gage asks, "If Milos has the most and arguably best beaches of all the islands in the Cyclades, plus ruins, plus good food, plus, plus, plus, how come nobody noticed until now?"

The Location: This volcanic island is in the Aegean Sea. There are regular flights from Athens in high season as well as a four-and-a-half hour boat ride.

The Insider Tip: There's more to Milos than crystal-clear water and idyllic swim spots. It's home to catacombs that rival the ones in Rome, has an ancient amphitheater that once held 7000 people, and has gorgeous cafés and shops in the capital.

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Santorini

Santorini Travel
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The Traveler: Santorini is perfect for true romantics. The breathtaking caldera in Oia might be touristy, but boy does it live up to the hype. Book a restaurant on the cliff, and sip on chilled wine from a carafe while the sun sinks into the horizon.

The Location: One of the Cyclades islands in the Aegean Sea, Santorini is best known for its stunning cliff face caused by a volcanic eruption in the 16th century BC.

The Insider Tip: Hotels are incredibly popular on the caldera in Oia, so prices skyrocket in high season. We stayed in a local bed-and-breakfast set back from the caldera—it was within walking distance from the best restaurants and viewing spots, and cost a fraction of the price.

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Kefalonia

Kefalonia Beaches
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The Traveler: Kefalonia is perfect for wine lovers. It's the largest Ionian island and boasts a mountainous landscape with plenty of vineyards.

The Location: It's positioned just west of mainland Greece, making this island the perfect stop for those who want to add a beach destination to their vacation.

The Insider Tip: The heat can be unbearable in August, so travel in the shoulder season for warm weather that's still pleasant.

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Folegandros

Folegandros—Greek Islands Guide
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The Traveler: Anyone looking for a truly restorative vacation. "Come here if you truly want some downtime—there are no parties till dawn happening here," says traveler Jessie Bush.

The Location: Folegandros is a small island in the Aegean Sea. It's close to Santorini, making it an ideal second stop on your island-hopping adventure.

The Insider Tip: Hire a boat if you want to reach the best beaches, says Bush, who notes Folegandros is one of her favorite islands in the region. It boasts "untouched beaches (largely thanks to the fact that they are only accessible by boat), whitewashed streets dotted with locals and endless views over the horizon."

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Planning another European escape? Here's why you should consider Croatia, another stunning country that's made for island hopping.

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