Fall Is Actually the Best Time To Visit These Greek Islands

Ask a few New Yorkers where they’re going for the summer, and you’ll usually notice a theme. Summer is one of the best times to escape Manhattan and its surrounding boroughs, and city dwellers are zeroed in on the best places to seek refuge—it’s usually somewhere with a great beach. For summer 2024, Greece was one of the most popular destinations to visit, and more specifically, the Greek Cyclades Islands, a surrealistic cluster of 200 inhabited islands in the Aegean Sea, each with its unique personality, all accessible by ferry. You can visit just one or plan a trip to multiple islands in one go. While summer is undoubtedly a great time to visit the area, fall is when those in the know plan a vacation there. Crowds are sparser, the sea breeze is stronger, and in some cases, you’ll feel like you have the islands all to yourself. But with hundreds of localized towns, deciding which ones to visit for the first or even second time can be tricky. You’ll want to return to some repeatedly, while others will be in your memories for years. But one thing is sure—you’ll never get tired of the country's picturesque Mediterranean landscape, fresh seafood and local olive oils, exceptional wines, and heartwarming people. Here are the best Greek Islands to visit this fall—from the closest to Athens to the farthest—plus where to stay and what to put on the itinerary.

If you’re starting in Athens and want a few days to rest and recoup before you head off to the islands but don’t want to limit yourself to staying in the city's center, the Athenian Riviera—about a 45-minute drive from Athens International Airport—is the best area to stay. Located on the coast in the southern suburbs of Athens, you’ll be less than 10 miles from downtown, so you can still easily take in the ancient history of the Acropolis, Ancient Agora, and the streets of Plaka but still feel like you’re kicking off the seaside vacation with chic accommodations directly on the water. The Four Seasons Astir Palace Hotel Athens is the best new place to stay for that—and it’s so secluded you almost feel like you shouldn’t know about it. Luxurious rooms and villas, many with sea views, are much bigger than you’d get in the nearby city. Plus, if you’ve been to Athens before and want to stay tucked away from the hubbub, the resort is an excellent option with an intimate beach club set directly on the Riviera, an expansive pool, and a spa. Plus, there are multiple restaurants, including a traditional-style Greek Taverna 37, where you can order classical dishes like moussaka, souvlaki, and octopus. When you’re ready to explore your next destination, you’re only half an hour from the Port of Piraeus to hop on a ferry or can easily head back to the Athens airport for a quick flight to the islands.

Kéa Island, locally known as Tzia, is so under the radar that some Athenians haven’t even heard about it. But within 45 minutes of Athens via ferry, it’s an extremely accessible destination and a great place to begin your island hopping journey. What’s been described as a “weekend” destination for locals, similar to the Hamptons for Manhattanites, the island, which has a year-round population of only about 3,000 people, is comprised of a hilly, primarily dry terrain. It makes for really picturesque 360-degree views of the Aegean Sea, and rain is rarely in the forecast. Located at the peak of one of those hills lies the idyllic newly opened One & Only Kéa Island property nestled into the cliffside, sitting on a naturally formed peninsula. The serene structure blends perfectly with the surroundings studded with one-bedroom villas, all with private pools and homes that are so incredibly chic you’ll find yourself promptly googling the name of the architect (it’s John Heah, known for his impeccable design ethos behind luxe properties like Aman). Filled with vast, airy open spaces, the lobby and restaurant are a full indoor-outdoor experience with expansive sea views beneath. Their Bond Beach Club is situated directly on the water, a destination for guests and locals alike that is accessible by boat and offers a great way to spend the day and have a beachside lunch. A state-of-the-art spa also utilizes the Greek concept of sophrosyne, emphasizing balance and soundness of mind.

During your stay, you must visit the charming town of Kéa, which is filled with narrow winding alleys and dotted with local artisan and pottery shops. Visit the summer home-turned-studio of the legendary Greek artist Alekos Fassianos, whose tiny home on a hill has been preserved just as he left it after passing in 2022. Authentic cuisine, like freshly caught fish and robust veggie dishes, is easy to come by in the town at the local eateries, and for a special dinner, join Atria’s open-air kitchen, where they produce specialty dishes and live entertainment from local musicians. Visit the speakeasy just steps away for some Metaxa, a Greek brandy that's often enjoyed after dinner.

Either a half-day ferry or a 45-minute flight from Athens, Paros is one of the fastest-growing islands in the Cyclades, and much of its popularity has to do with the fact that the island holds something for everyone. Whether you want to experience the party life of Mykonos or have a taste of the local life, you can do it all on the island, which comprises beaches, mountains, and old relics from the sixth century B.C. The larger port towns of Naousa and Parikiai are lively day and night with great independently owned boutiques—Saline Shop is a must-visit in Naousa—and cafés and restaurants lining the port. For a central hotel location equidistant to both main towns, stay at Andronis Minois, a 44-room boutique hotel designed in the quintessential Cycladic style of architecture with white facades, Mediterranean sea views, and beautiful bougainvillea landscaping.

While Andronis Minois is centrally located and has great amenities like a beautiful pool you can easily lay by all day long, renting a car allows you to explore the island independently, and there are lots of old towns, like Lefkes and beaches—like Faragas, Kolymbithres, Santa Maria and Golden Beach— to check out during your stay. For a day trip from Paros, you can also hop on a 7-minute ferry and head into Antiparos, the tiny Greek island next door that’s a favorite amongst celebrities like Tom Hanks (who owns a home there). For a half or full-day excursion, book a daybed at Soros Beach Club—one of the best, if not the best beach in Antiparos. Alternatively, you can book a boat charter—Seacret Cruises is a great one—and explore hidden coves, beaches, and landmarks accessible only by water.

Known for its specialty cheeses and locally produced wine, Paros is also a great eating destination for foodies. Arodo, a tiny local beach club and restaurant where you’ll practically eat on top of the ocean, has excellent seafood, pasta, and a million-dollar sunset view. Perched up on a hill, Anthi Meze in the small port town of Piso Livado serves traditional Greek recipes, like stuffed peppers and spinach pies, all homemade. For a special dinner looking over Parasporos Beach, book a table at Olvo Restaurant that utilizes the local flavors of Paros and nearby islands for dishes like Greek salad, fresh fish, and seafood.

Unsurprisingly, people are drawn to Santorini for its jaw-dropping views and picturesque white-and-blue buildings carved into the Caldera’s cliffside like something straight out of a fairy tale. The town that’s a bucket-list destination for many can get crowded in the high summer months, but fall lends a quieter experience, especially if you can find places off the beaten path but with all the charming qualities you would want from visiting Santorini. With most of the main attractions happening in the two main towns of Oia and Fira (a scenic 2-hour hike from one to the other is a popular activity), staying adjacent to them (but not necessarily in them) is always a good choice, within walking distance to restaurants and shops but not smack dab in the middle. Andronis Arcadia’s luxurious resort-style property has a great location, catty corner to Oia, just a stroll from the Caldera side, with all the luxuries of a five-star resort. Rooms are modern and spacious, with private plunge pools and the largest pool for guests in Santorini, overlooking the Aegean sea; plus, it has excellent sunset views and two popular restaurants. Again, this is another place you could spend the day by the pool(s)—there are several—but there are a few must-visit places to check off first.

One is the nearby Ammoudi Bay, a small port town located 278 steps below Oia. It's lined with seafood restaurants and a great swimming hole with a popular rock formation to jump off. It’s also a popular spot for boat tours, and chartering one is a great way to see the volcano by water, visit hidden beaches—like the red beach or the blue—and swim in the hot springs.

If you’re looking for something other than sand and surf, the brand-new Ftelos Brewery Santorini is worth stopping for a flight of their latest craft beers, from German-style lagers to in-house flavors like hibiscus saison. There’s an expansive outdoor terrace and rooftop, and the food at their onsite MALT restaurant is not to be overlooked, serving unique dishes like anchovies stuffed with cheese from the nearby island of Naxos and homemade spaghetti and octopus with Greek saffron.

For other memorable meals on the island and easier reservations to secure in the fall, visit Metaxi Mas, a Greek tavern perched on a hill in Exo Gonia village with authentic Greek fare. The Good Heart, a family tavern with a fresh seasonal menu near the village of Akrotiri, and The Dolphins, a small fish tavern located directly on the water. The popular Beefbar restaurant also has a location in Santorini, offering a serene setting for dinner, and serves up some of the best beef dishes, but with a local twist, like Kobe gyros, Greek salad, and fresh lobster tacos.