Indagare Matchmaker: What Are the Best Greek Islands for Different Kinds of Travelers?

Mainland Greece is surrounded by enchanting archipelagos comprising 2,000 islands, of which approximately 170 are populated. Santorini and Mykonos are justly famous, but there are other isles that also have rich histories, ancient ruins, varied landscapes, charming medieval villages and unspoiled beaches ready to be explored. Here, Indagare shares the best Greek islands for different kinds of travelers.

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Best Greek Island for Romantics: Santorini

Almost otherworldly in its dramatic beauty, Santorini is all about the simple pleasures of summer in Greece: sun, sand and the obligatory evening aperitif. The Aegean island is a caldera, with steep cliffs and towns dotting the upper ridge. Its unique C-shaped crater is the result of the second-largest volcanic eruption in world history, which took place 3,600 years ago. It is widely believed that this event is the source for the legend of Atlantis. True or not, Santorini has an undeniable air of mystery that enhances its idyllic charm.

Overview: Primarily a relaxation destination—guests can easily while away an entire day lounging poolside—Santorini also offers rich volcanic vineyards, red- and black-sand beaches, underwater treasures and prehistoric ruins.

Getting There: Fly into Athens and then take a 45-minute flight to Santorini.

Where to Stay: Katikies Kirini Santorini or Canaves Oia Hotel & Suites

Highlights: Going on a boat cruise with stops for snorkeling; visiting a winery; hiking; relaxing at your hotel; touring the ancient city of Akrotiri

Best Greek Island for Scenesters: Mykonos

Often referred to as the Capri or St.-Tropez of Greece, Mykonos seamlessly combines sandy beaches and a charming, authentic town, much-photographed windmills, chic hotels, sophisticated restaurants and an exciting night life.

Overview: Mykonos is defined by pebble-stone streets, pretty squares surrounded by whitewashed houses and a main town that is adorned with pots of geraniums and bougainvillea. It’s a joy to get lost exploring the boutiques, galleries, restaurants, bars and churches here.

Getting There: Fly into Athens and then take a 35-minute flight to Mykonos.

Where to Stay: Santa Marina Resort & Villas and Kalesma

Where to Eat: Captain's Food for Sharing and Kiki’s Taverna

Highlights: Scorpios; visiting the ruins at Delos; shopping at small local shops like Salt Boutique; and partaking in the nightlife scene at Nammos

Best Greek Island for Culture Lovers: Paros and Antiparos

Paros, the second-largest Cycladic island, reached the apogee of its glory during the Classical period, thanks to its world-famous marble. It is spotted with ruins, evidence of occupation by a series of cultures and civilizations going back to 3,200 BC. A longtime cultural hub, it attracts international artists and art aficionados to its contemporary exhibitions and events. Just off the coast of Paros, tiny Antiparos has largely escaped the effects of mass tourism and boasts lovely turquoise water, pristine beaches and stunning stalagmite caves.

Overview: Paros offers the best of the Cyclades: whitewashed villages, charming harbors and secluded coves, along with a rich cultural scene. Naousa and Parikia are both popular areas with a lively nightlife and some of the best restaurants on the island.

Getting There: Take a direct flight from Athens or a ferry from Santorini or Mykonos.

Where to Stay: One of Indagare’s favorite private villas

Antiparos Highlights: Visiting the beaches of Psaraliki and Soros; watching the breathtaking sunset from Vathys Volos; and canoeing or kayaking between Antiparos and Despotikon

Paros Highlights: Windsurfing at Golden Beach or relaxing at Santa Maria Beach; exploring the historic village of Lefkes, filled with local boutique stores and cute cafés, like Cafe Marigo; and booking a boat charter around the island

Best Greek Island for Beachgoers: Milos

Milos—the southernmost island in the Cyclades group—is positioned between mainland Greece and Crete, and is still slightly under-the-radar (for the time being). An island that has it all, Milos is an island you could easily spend four-to-five nights and not run out of things to do or see.

Overview: Milos is known for its striking volcanic landscape and wide variety of beautiful beaches, making it one of the more romantic Greek islands (according to locals). The best way to see all of Milos is by renting a car and visiting the hidden gem fishing villages and unique beaches that dot the island, or by chartering a boat to get to Milos's caves and bright turquoise water (inaccessible by foot). It seems to be an island that has it all—local stores to peruse; gorgeous landscapes to admire; friendly locals to meet; and delicious restaurants with fresh Greek cuisine and sunset views.

Getting There: Take a direct flight from Athens or a ferry from Santorini or Athens.

Where to Stay: One of Indagare’s favorite private villas

Where to Eat: Kivotos ton Gefseon and Palaios Coffee & Pastry for breakfast, brunch or snacks; O! Hamos! Tavern for lunch or dinner; and Ergina for dinner at sunset

Highlights: Walking around Plaka Village and climbing the hill to Plaka Castle for sunset; visiting the old fishing villages of Firopotamos and Klima; experiencing the island's diverse array of beaches such as Paleochori, Sarakiniko (the otherworldly, lunar-like beach) and Papikinou; and embarking on a boat day to visit the Sykia and Kleftiko Caves, only accessible from the water

Best Greek Island for Being Under-The-Radar: Syros

Situated in the center of the Cyclades, Syros is an island with rich history and great importance. Due to its geographical position, the capital of Ermoupoli became known as a significant port town and maritime way-point, and was even used as a secure shelter during the Greek Revolution in 1821, attracting many Greek refugees from surrounding islands who ended up building the capital. This, plus the island's Venetian background, plays into the abundant culture that exists on the island today.

Overview: For those who are looking for something lesser-known in the Cyclades island group, Syros is a hub for culture, laid-back locals and some of the best food in Greece. They have a year-round arts scene with numerous festivals ranging from international film to classical music, and while pastel-colored Ermoupoli may be small, the nightlife measures up to some of the much larger islands. The travelers here are self-sufficient and searching for authentic experiences—and three-to-four nights in Syros can be filled with a bit of everything: relaxation, sunsets, gorgeous views, history, adventure and mouthwatering local cuisine, all without the crowds.

Getting There: Take a direct ferry from Athens (two hours), Mykonos (30 minutes) or Paros (one hour and 30 minutes).

Where to Stay: Aristide Hotel

Where to Eat: Try To Tsipouradiko tis Mirsinis in Ermoupoli and make your way up to Ano Syros for Maison De Μεζέ and Chýma Kai Tsouvaláta

Where to Shop: Syros has really great boutiques on the main drag and in the alleyways of the port town, Ermoupoli. Just a couple streets in from the port, you can find Daphne Velli, Desperate Design and Sandalia Cyclades. In Ano Syros, you can find a smaller Desperate Design location and Rosa Negra.

Highlights: Strolling through the whitewashed, bougainvillea-filled Ano Syros alleyways and encountering friendly locals and breathtaking views; shopping at the local boutiques in Ermoupoli; visiting the Catholic Cathedral of Saint George and the Church of Agios Nikolaos to see their amazing interiors; relaxing at the local beaches, like Agathopes, Galissas or Kini; and renting an ATV or scooter to drive around the island, stopping at local tavernas or hiking paths along the way.

Related: Secret Greece: Our Favorite Under-the-Radar Greek Islands

Best Greek Island for Adventurers: Crete

The largest island in the Aegean Sea, Crete has a diverse terrain, from snow-capped mountains to pristine beaches to dramatic gorges, as well as resorts offering a comprehensive list of amenities. As the birthplace of the Minoan civilization, it will enchant ancient history buffs, and active types will enjoy trekking through its jagged ravines, snorkeling in its aquamarine water and sailing to remote coves during their visit.

Overview: Greece’s largest island offers a dynamic mix of historic ruins, varied landscapes, glamorous hotels and beautiful beaches.

Getting There: Take a direct flight from Athens, a private helicopter from Mykonos or a hydrofoil from Santorini.

Where to Stay: Elounda Beach, a grand waterfront resort with villas and bungalows

Highlights: Visiting the ruins of Knossos, the Minoan capital, boating to Spinalonga island, trekking the Samarine gorge, snorkeling, rock climbing, hiking

Best Greek Island for Families: Corfu

Located in the Ionian Sea west of mainland Greece and a one-hour flight from Athens, the island of Corfu is markedly different from the small, windswept Cyclades in size—it is about ten times as large as Santorini—and topography, with lush landscapes that are green year-round, thanks to heavy rains in the winter.

It also differs in its culture, which, due to its proximity to Italy, displays a strong Italian influence in its cuisine and architecture. Corfu Town is a UNESCO World Heritage Site, with neoclassical mansions, wide piazzas and three forts designed by Venetian engineers. The island has spectacular swimming coves fringed with tropical plants and fruit trees, as well as Greece’s largest selection of private villas, making it an ideal spot for a family vacation.

Overview: Corfu is a lush gem of an isle evincing strong Italian influence in its cuisine and architecture.

Getting There: Take a one-hour flight from Athens.

Where to Stay: One of the island’s many private villas or Corfu Imperial, a seafront luxury resort

Highlights: Wandering around Corfu Town, a UNESCO World Heritage Site, visiting the many small bays and beaches, yachting to the pristine isles of Paxos and Antipaxos

Where to Stay? Try a Greek Villa Rental

Greece boasts some of the most spectacular private villas in the world, with incredible sea views, open-air layouts and true privacy, plus luxe amenities like private pools, gyms, beach fronts, movie theaters and helipads. Indagare has excellent relationships with the islands’ top villa agencies and can help choose the best villa for your group based on your destination and interests. We can also arrange for private chefs, instructors and babysitters, as well as organize excursions and on-property activities.

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We only feature hotels that we can vouch for first-hand. At many of them, Indagare members receive special amenities.

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