As a luxury travel advisor, Greece has long held a special place on the itineraries I design. I’ve planned everything from romantic honeymoons to milestone birthdays, multigenerational escapes to cultural deep-dives. It’s a destination I’ve gotten to know intimately through research, trusted partners, and the firsthand stories of my clients over the years.
But this summer, I had the opportunity to explore Greece like my clients do – first one on one with my newly graduated son, then as a family when my husband joined us, and finally with our extended family for a grand finale in Crete. The variety of experiences took my appreciation for the country to an entirely new level.
Every stop, every island, had its own unique personality. The contrast and variety of landscapes, energy, cuisine, and history, was what struck me most. And while I’ve always known Greece is special, it’s something else entirely to feel it firsthand, to watch the light shift across the Aegean, to taste the herbs growing just beyond your terrace, to experience the hospitality that makes “philoxenia” more than just a word.
Here are a few highlights from our journey:
Athens: Where Legends and Luxury Meet
Athens provided the perfect starting point—steeped in ancient history, but buzzing with modern life. Our private Acropolis tour was a standout. Our guide was brilliant, engaging, and connected so well with my son that it made the past feel immediate and alive.
And our base, the Four Seasons Astir Palace, was simply unforgettable. This iconic resort has long been a favorite among those in the know, and it’s easy to see why. With its glamorous history (Jackie O. was a regular) and effortless modern elegance, it’s a perfect blend of old and new. Every detail was flawless – the dining opportunities in particular were incredible, but of course the seamless Four Seasons service and sweeping sea views set the tone for a perfect stay.
Mykonos: Glamour with a Heartbeat
Mykonos was dazzling in the best possible way – but also surprisingly warm and welcoming. We stayed at Mykonos Grand, a property that delivers serious luxury without ever feeling formal or stuffy. The rooms were gorgeous, the food was excellent, and the service was both polished and deeply personal.
We loved the easy access into town for dinners and nightlife via the complimentary hotel shuttle, and our boat day to Delos (complete with a private guide and a captain who prepared us an incredible lunch on board) was a top-tier experience.
Paros: Soulful Simplicity
Paros brought a sense of calm that we didn’t even know we needed. The island’s slower pace and unpretentious charm made it a true standout.
At Andronis, we found a property that struck just the right note: luxurious, but low-key. The service was warm, the food genuinely memorable, and we left feeling completely recharged.
Santorini: A Destination Within a Destination
There’s a reason Santorini is on so many dream lists—and Canaves Oia Suites makes that dream feel entirely real.
What I loved most was how the hotel felt like part of the village itself; tucked into the cliffs just enough to feel hidden, yet central enough to feel immersed. Our suite had a private pool and overlooked the caldera, and every space throughout the property felt like a quiet, design-forward celebration of place.
Each suite is elegant yet playful, with unexpected touches that make you feel like you’re living in the destination, not just visiting it. Sunset cocktails at Canaves Sunday Suites followed by a moonrise at Ena on our final night? One of those moments you mentally file under unrepeatable.
Crete: Space, Flavor, and Family Joy
Crete was a beautiful surprise: expansive, grounded, and deeply generous.
We stayed at Domes of Elounda, a resort that does an exceptional job blending style with family-friendly ease. There’s a chic food truck village for casual dining (a huge hit with all of us), a thoughtful layout with privacy baked in, and tons of activities for kids and adults alike.
One of my favorite parts? A family photo shoot, which I always recommend for multigenerational or milestone trips. We also spent a day visiting a local winery and participating in a hands-on cooking class—an experience that brought both laughter and learning, led by a guide who felt like an old friend by the end.
The team at Domes went above and beyond for our family celebrations, and the property left a lasting impression.
Final Thoughts: One Country, Many Personalities
One of the most rewarding things about traveling through Greece is how distinctly different each island feels. You can hop just a short distance and feel like you’ve landed in an entirely new world, one with its own pace, palette, and point of view.
That’s part of what makes it such a rewarding destination to plan. Whether you’re craving cliffside sunsets and romance, a culinary deep dive, or a carefree family adventure, Greece can rise to meet you.
This trip was personally meaningful in so many ways, and professionally reaffirming too. If Greece is on your list (or if you’ve been before and want to see it from a new angle) I’d love to help you design an experience that fits exactly who you are, and how you want to feel.
Rebecca@Wanderology.com 