The Best Greek Island for Your Vacation, Based on Your Enneagram Type

Planning a vacation to the Greek islands this summer, but don’t know where to start? First up, you made a great choice. Greece is consistently recognized as one of the world's top holiday destinations–in 2024 it claimed the title for “Europe’s Leading Destination 2024” at the World Travel Awards (WTA). The country features over 200 inhabited islands, each with its own personality and charm. But with so many options to choose from, it can be difficult to know where to go. 

The good news is that the Enneagram can be used for a wide range of things, including travel planning. Whether you’re seeking adventure, tranquility, cultural immersion or Instagrammable images,  your Enneagram type can guide you to an island that aligns perfectly with your inner motivations. 

Below we offer you a guide to the best Greek island for your holiday, based on your Enneagram type.

Type 1 Perfectionist → Lefkada, the Most Accessible Greek Island

As a practical, organized and detail-oriented traveler, you—our problem-solving Type 1—will find Lefkada in the Ionian island cluster an ideal destination. It’s one of the few Greek islands you can drive to, connected to mainland Greece by a floating bridge that takes just a minute to cross. This means no worries about ferry strikes or weather-related travel delays, allowing you to enjoy your well-planned journey stress-free. 

We know you have high standards so you will be happy to learn the island is home to five “blue flag beaches,” the international symbol for excellence in terms of water quality, amenities, and environmental standards. Add in delicious local cuisine and welcoming hospitality, and you have a destination that checks all your boxes for a perfect, hassle-free holiday.

Type 2 Giver →  Sifnos, the Foodie Island of Greece

Your focus is on your relationships and even when you travel, it is as much to cultivate your emotional bonds as it is to sightsee. That’s why you–our empathetic Type 2– will love Sifnos, the foodie island of Greece because what better way to connect than over exceptional food? Named “Greece’s most delicious island” by Conde Naste, this lesser known destination in the Cyclades island grouping is growing in popularity because of its innovative culinary scene. Stroll along the stunning beach at Platis Gialos and choose from any of the amazing restaurants along the sea–you might even find Tom Hanks at his favorite fish bar, Omega3.  

We know you like to take gifts back to the folks at home so you’ll be happy to learn Sifnos is also the pottery capital of the Aegean. Buy a few locally crafted plates and bowls as presents for your friends and family, and you’ll keep your culinary bonding up long after you get home.

Type 3 Achiever → Santorini, the Most Photographed Place in Greece

It goes without saying that capturing stunning photographs will be an important part of your trip, so you –our image-conscious Type 3– should head to Santorini, one of the most photographed places on Earth. The island’s dramatic caldera, whitewashed buildings, and distinctive blue-domed churches have become synonymous with Greece’s beauty. You can take in the famous sunset overlooking the cauldron or hike from Fira to Oia where you’ll pass plenty of natural beauty to frame the iconic images. 

Santorini combines both traditional Greek island architecture and modern luxury accommodations making it both a historical and chic destination. This island gets really busy so head here in the shoulder season months of May and October for your best experience.

Type 4 Individualist→ Gavdos, the Most Southern Point in Europe 

You have a taste for the eclectic and prefer to avoid the crowds so head to Gavdos, the remote island off the coast of Crete and home to the southernmost spot in Europe. With a full-time population of under 200 people, Gavdos is one of Greece's best-kept secrets, offering you–our emotionally-intense Type 4–tranquil a retreat, perfect for reflecting on life and offering you time to process your feelings from the last year. 

With pristine, secluded beaches like Sarakiniko and Agios Ioannis, as well as unique landmarks like the iconic Gavdos Lighthouse and the giant chair marking the edge of Europe, the island provides an unmatched experience of natural beauty and history. You’ll appreciate the island's simple, laid-back, authentic atmosphere. Head to Gavdros for a peaceful, off-the-grid holiday.

Type 5 Investigator→ Samothrace, the Most Mysterious Island in Greece

You are deeply private and a bit of a mystery to others so you–our reserved Type 5–will probably feel a kindred spirit with Samothrace, the home of ancient mystery schools and the secretive Samothracian Rites. In times past, this island in the North Aegean island cluster was the home to a mystery cult, drawing thousands of followers from ancient Greece and beyond to participate in sacred rituals. Today, you can reimagine these rites when you visit the ancient ruins of the Sanctuary of the Theoi Megaloi (Great Gods). 

The island itself will appeal to your love of nature and your sense of self-sufficiency. Camping is a popular activity here due to all the raw natural beauty including cascading waterfalls, natural rock pools, and lush forests filled with oak and cedar trees. This unpretentious island gives you plenty of opportunities to connect with your primitive self as Samothrace has remained largely off the radar for mass tourism so you don’t need to fear the maddening crowds.

Type 6 Skeptic → Tinos, Greece’s Most Dutiful Island

You–our loyal Type 6– value tradition and seek an honest, authentic scene which is why the island of Tinos is perfect for you. More low profile and less flashy than its neighbor Mykonos, the island of Tinos draws a more reflective and devoted crowd. It is home to the Church of Panagia Evangelistria, one of the most significant pilgrimage sites in Greece. The church is dedicated to the Virgin Mary and houses a miraculous icon believed to have healing powers. 

Each year on August 15th, thousands of pilgrims come from all over the world, often crawling on their hands and knees from the port to the church as an act of devotion​ and to pray for miracles. You’ll love the tradition, along with the charming villages, good value food,  and warm hospitality from the locals. Head to Tinos and pray for those miracles you hope for.

Type 7 Enthusiast → Mykonos, the Party Island of Greece

You like a good time–our adventure-seeking Type 7– which is why the party island of Mykkonos is our pick for you.  This marquee island in the Cyclades has rightfully earned its world famous reputation for its vibrant nightlife, superstar DJs, and fun-loving crowd. With clubs like Paradise, Super Paradise, and JackieO’, you’ll have lots of options for an entertaining night on the town. 

But Mykonos isn’t just a party–it is the home to stunning beaches and just a stone’s throw from the sacred island of Delos. Go with your urge to cram it all in and take a quick afternoon trip to Delos to explore the mythical birthplace of Apollo before heading back to Mykonos Town for dinner and dancing.  You are sure to have a good time in Mykonos.

Type 8 Challenger → Crete, the Island of Rugged Independence and Vendettas

You are interested in power and power dynamics so you–our resourceful Type 8–will love Crete, Greece's island of rugged individualism. The largest island in Greece and the 88th largest island in the world, Crete features remote mountains and beautiful beaches alongside a rich history/ Cretan resistance to the Germans during WWII is credited for being part of why the Allies won the war. 

Resistance isn’t the only thing the island is famous for–Crete is also known for its family vendettas, historically seen as a way of seeking revenge and maintaining honor. The good news is that vendettas are mainly a thing from the past so you can focus on visiting Knossos Palace, the home of the Minotaur or the island’s famous beaches like Elafonissi, a stunning seaside with pink sand. You’ll love how much this island has to offer but be sure to rent a car so you have full control to go and see what you want.

Type 9 Peacemaker→ Milos, Home to the Most Beautiful Beaches in Greece

While you–our harmony-seeking Type 9– are often called the most powerful type in the Enneagram, you are so low-key that your talents are often overlooked so you might feel a special affinity to Milos, the low-profile island that is home to the best beaches in Greece. This under -the-radar destination in the Cyclades cluster offers over 40 impressive beaches including Firiplaka, Triades, and more. 

Spend your day beach hopping and then head up to the charming capital town on a hill for an amazing fish dinner. This island has something for everyone and from the other-worldy rock formation at  Sarakinikos to the Milos Mining Museum, Milos can accommodate almost any traveler’s taste. Head to Milos and be ready to be pleasantly surprised.

In Summary

As you can see, the Enneagram offers a powerful compass to decide which Greek island is right for you. But just to be sure, maybe you should visit all the islands on this list so you can compare and contrast. An island hopping adventure is never a bad idea!