Beyond the Usual Greece
Our Advisors’ Favorite Places to Explore
Dreaming of your own Greek Odyssey? From celebrated islands to lesser-known coastal escapes, Greece offers something for every kind of traveler.
To inspire your next journey, five Avenue Two advisors are sharing the destinations and experiences they can’t stop thinking about. And while Greece may be synonymous with summer, it is every bit as dreamy in spring and autumn, often with fewer crowds, comfortable temperatures, and a more relaxed pace.
Recommended by Carissa Cummings –
Travel with Virtus
Athens: Give This City More Time
Athens is a sprawling city where ancient history and modern life meet and while many travelers rush through to their island escape or cruise, I always encourage at least two nights here (if not three).
Climb or take the funicular to the top of Lycabettus Hill for sweeping views across the city, then wander through the stylish streets of Kolonaki, known for its beautiful boutiques and excellent restaurants. The not-so-new Acropolis Museum is incredible in conjunction with a visit to the Parthenon.
For an unforgettable evening, I suggest venturing out to Cape Sounion to watch the sun sink into the Aegean from among the ancient ruins of the Temple of Poseidon.
Athens offers an impressive collection of hotels, but the new Conrad Athens The Ilisian is poised to become a standout.
Recommended by Hannah Aiken –
Hannah Aiken Travel
Costa Navarino: Mainland Greece’s Best-Kept Secret
Costa Navarino is one of mainland Greece’s best-kept secrets. It also served as the backdrop for scenes in Christopher Nolan’s The Odyssey, including the legendary Cyclops cave. I had the opportunity to bike and hike to the cave, and the scenery was every bit as memorable as its cinematic connection.
Home to four luxury resorts, The Romanos, a Luxury Collection Resort; The Westin Resort Costa Navarino; W Costa Navarino; and Mandarin Oriental, Costa Navarino, the destination offers championship golf courses, lively agoras, beautiful beaches, and an incredible variety of experiences across the properties.
For travelers seeking a true full-service luxury resort experience in Europe, Costa Navarino is one of the few destinations that genuinely delivers it all.
Recommended by Madeline Radway –
Madeline Radway Travel
Milos and Santorini: Authenticity Meets Iconic Beauty
I first visited Milos for a close friend’s wedding in 2023. Because the bride’s family is from the island, I was fortunate to experience its true heart and soul: traditional food (don’t miss the pitarakia!) spectacular beaches extending far beyond Instagram-famous Sarakiniko, and warmhearted locals whose families have lived there for generations.
It is an island I can’t stop dreaming about, and everyone I’ve sent there returns saying the same. You could easily spend weeks exploring Milos, but it also pairs beautifully with iconic Santorini.
Although Santorini is heavily visited, I still wouldn’t skip the breathtaking caldera views from a private-pool suite in Oia. Combining the two islands creates a perfect Cycladic itinerary that balances Santorini’s undeniable wow factor with Milos’ authentic island culture.
Recommended by Deb Swacker –
227 Travel
Hydra and Spetses: Effortlessly Chic Island Escapes
On my two most recent trips to Greece, I was lucky enough to explore Hydra and Spetses, two Saronic Islands located within easy reach of Athens. Both are largely car-free, wonderfully atmospheric, and effortlessly chic.
Spend your days wandering picturesque streets, relaxing at the beach, browsing local boutiques, and lingering over leisurely meals, but don’t skip a day on the water.
If you can time your visit to coincide with the Spetses Classic Yacht Regatta and stay at the iconic Poseidonion Grand Hotel, even better. You won’t be sorry.
Recommended by Ann Harrison –
Ann Harrison Travel
Santorini: So Much More Than a Sunset
For me, it’s Santorini all the time. I discovered that there is so much more to the island than its picture-perfect sunsets. Ancient ruins, vineyards, excellent wines, peaceful villages, and extraordinary sea views around nearly every corner make Santorini a destination worth exploring slowly.
Take a catamaran cruise to reach secluded swimming and snorkeling spots while experiencing the island’s dramatic cliffs from the water.
And don’t miss the Canaves properties. I loved the chic, relaxed atmosphere at Canaves Epitome, but I would pair it with a stay at Canaves Oia on the caldera. Together, they offer two distinct perspectives—and the complete Santorini experience.
Ready to Plan Your Own Odyssey?
Whether you’re drawn to the iconic views of Santorini, the authentic charm of Milos, the understated elegance of the Saronic Islands, or the full-service luxury of Costa Navarino, Greece rewards travelers who look beyond a one-size-fits-all itinerary.
Our advisors can help you choose the right destinations, hotels, and experiences, and design a journey that feels entirely your own.
Ready to begin?
Reach out to your Avenue Two Travel advisor to start planning your Greek adventure.
