Greece offers a stunning mix of landscapes, history, and culture, making it a favourite for luxury travellers. Whether you’re drawn to the famous caldera views of Santorini or the quieter, volcanic shores of Milos, there’s something special in every corner of this Mediterranean paradise. This guide highlights five fantastic destinations for a luxury Greek holiday, with suggestions on what to see and do, and tips to make your trip even smoother! 

Crete: The Island of Diversity and Adventure

Crete’s vast size means it offers something for everyone, from mountains and gorges to sandy beaches and historic sites. For a luxury trip with plenty to do, this island is hard to beat!

Hiking the Samaria Gorge early in the morning is one of the best ways to experience Crete’s rugged interior. The 16-kilometre trek takes you through dramatic landscapes and ends at the Libyan Sea, where you can cool off after the hike. If hiking isn’t your thing, no problem! The island’s many beaches offer equally stunning beauty. Elafonissi, with its pink sand and shallow turquoise waters, feels like a private paradise. 

History buffs should explore the Palace of Knossos, the legendary Minoan palace linked to the myth of the Minotaur. The site’s ruins tell stories of an ancient civilisation that thrived on the island thousands of years ago.

For a slower pace, head to traditional villages like Archanes or Chania’s old town, where you can wander cobbled streets, explore local markets, and discover artisan crafts. 

Milos: Untamed Beauty and Relaxed Luxury

Milos stands apart from its Cycladic neighbours with its dramatic landscapes and less commercial vibe. Known for its colourful fishing villages and quiet beaches, Milos is perfect for travellers seeking a more laid-back luxury escape. There are some incredible Milos villas for rent, which offer privacy and beautiful scenery during your stay on the island. 

Sarakiniko Beach, with its striking white rock formations, is an unmissable spot for swimming and photography. Nearby, the fishing village of Klima is a photographer’s dream, with its vibrant boathouses right at the water’s edge.

One of the best ways to explore Milos is by boat. Private boat tours take you to hidden caves and secluded beaches such as Kleftiko, accessible only by sea. These tours often include opportunities to snorkel in crystal-clear waters, giving you a chance to spot marine life up close.

Don’t miss the ancient Catacombs of Milos, early Christian underground burial sites that offer a fascinating glimpse into the island’s past!

Athens: History and Modern Luxury Combined

While Athens might not seem like a traditional luxury destination, it’s an essential stop on any Greek itinerary. The city effortlessly combines its rich history with a vibrant, contemporary scene, ideal for travellers who want culture and comfort.

The Acropolis remains the crown jewel, and visiting early in the morning or late afternoon helps you avoid the busiest crowds. Nearby, the Acropolis Museum offers detailed insights into the artefacts and architecture you’ve just seen. 

Beyond these classics, book private guided tours that dive deeper into less-visited ancient sites like the Temple of Poseidon at Cape Sounion, where you can enjoy a sunset over the Aegean in peaceful surroundings.

Explore Athens’ neighbourhoods, from the narrow streets of Plaka filled with artisan shops to the more modern Kolonaki district, known for its galleries and boutiques. The National Garden offers a tranquil green space in the city, perfect for a leisurely walk or a quiet picnic.

Santorini: The Iconic Island with a Personal Touch

Santorini’s striking cliffs and deep blue waters create the perfect backdrop for any luxury trip.

Start your mornings by wandering the quieter villages such as Pyrgos or Megalochori, where you’ll experience narrow lanes and traditional Cycladic architecture. History lovers should not miss the archaeological site of Akrotiri, an ancient Minoan city preserved in volcanic ash, often called the “Pompeii of the Aegean.”

For outdoor enthusiasts, hiking the caldera edge from Fira to Oia is a must-do. This roughly three-hour walk offers stunning views of the sea and volcanic cliffs, giving you a fresh perspective away from the crowds. 

Santorini is also ideal for wine lovers. Many vineyards produce excellent Assyrtiko wine, a crisp, mineral-rich white native to the island. Booking a private wine tasting or vineyard tour lets you sample these wines without the rush, often combined with stunning views of the vineyards and the sea.

If you want to explore Santorini in style, opt for private Santorini tours where you can enjoy private drivers, curated routes, and local insights for a truly bespoke experience. 

Rhodes: Medieval Charm Meets Coastal Relaxation

Rhodes blends history and natural beauty in a way few other places can. The medieval Old Town, a UNESCO World Heritage site, is a labyrinth of cobbled alleys, grand fortifications, and lively squares.

Renting a car to explore beyond the Old Town reveals quieter parts of the island. The Valley of the Butterflies is a peaceful nature reserve where, during the summer months, thousands of butterflies gather in the shade of the plane trees, offering a magical experience for families and nature lovers alike.

For a taste of ancient history, visit Kamiros, the ruins of a classical city that dates back over 2,500 years. Nearby beaches such as Anthony Quinn Bay offer stunning turquoise waters ideal for swimming and snorkelling.

The village of Lindos, with its clifftop acropolis overlooking the sea, is another highlight. Exploring the narrow streets and climbing up to the ancient fortress provides breathtaking views and a connection to the island’s layered history.

Which Greek Region Will You Explore Next?

Greece’s luxury travel appeal is rooted in its ability to balance natural beauty, historic richness, and relaxed island life. Whether you prefer to wander through ancient ruins or vibrant towns, these five destinations offer something for every type of traveller. 

The key to a luxury trip here is mainly about refining the details, taking time to explore less crowded spots, enjoying local experiences at your own pace, and soaking in the atmosphere that makes Greece so special!