There are some trips that go exactly according to plan—and then there are the ones that remind you why having a travel advisor is a good idea!
My recent educational trip with Waterstone took me through Athens, Santorini, Mykonos and Cyprus over 10 days, giving me the opportunity to experience some incredible hotels, explore the islands and learn firsthand which destinations and properties I would recommend for different types of clients.
A Slightly Delayed Start in Athens
Unfortunately, my flight into Athens was significantly delayed, which meant I missed our planned afternoon exploring Plaka and some of the other activities on our itinerary. But I did make it to NEW Hotel in time for sunset cocktails with my fellow travelers so all was not lost!
NEW Hotel was a fun introduction to Athens with its contemporary, art-forward feel—a great option for clients who prefer something more modern and design-focused rather than a traditional European hotel. This hotel also boasts rooftop Acropolis views so it is the perfect location to return to in order to watch the sunset after a day of site seeing. I have to say that after a long day of flight delays, finally arriving, meeting up with the group and enjoying a cocktail as the sun went down was a pretty great way to officially start the trip.
I didn't get nearly enough time to explore Athens on this visit, but that's the beauty of travel—there's always a reason to go back. So I have an excuse to go back to see the Plaka, the Acropolis and the rest of Athens.
Santorini: More Than the Famous Sunset
After a restful night of sleep, we left Athens and flew to Santorini, where we checked into NOUS Santorini for two nights.
Santorini is one of those places everyone has seen a thousand times in photographs, but there is still something pretty spectacular about seeing the caldera and those whitewashed villages in person.
Our first evening took us to Oia for a walking tour, sunset and dinner. Yes, Oia is busy and everyone wants that famous sunset view—but it's famous for a reason.
What I particularly enjoyed about this trip, though, was experiencing some of Santorini beyond Oia.
We visited a local winery and tasted the Assyrtiko and Vinsanto wines Santorini is known for. The island's volcanic soil and unique growing conditions make its wine culture especially interesting, and a winery visit is something I would absolutely incorporate into a client's stay here. One of the most fascinating things I learned in Santorini was how they grow their grapes. Because of the island's strong winds, intense sun and volcanic landscape, the vines aren't grown upright in traditional rows. Instead, they are trained low to the ground and woven into a circular, basket-like shape called a kouloura. The grapes grow protected inside the basket, shielding them from the wind and sun while allowing the vines to capture precious moisture from the sea mist and morning humidity. It's a centuries-old technique that's unique to Santorini and one of the reasons the island's Assyrtiko wines have such a distinctive character.
We also had time to explore Fira before returning to NOUS for a property tour and dinner.
NOUS itself offers a very different Santorini experience from the cliffside cave hotels most people picture. It's contemporary, spacious and resort-like, with a beautiful pool and spa.
That's exactly why seeing hotels firsthand is so important for me. There isn't one "best" hotel in Santorini. There is a best hotel for a particular client.
On to Mykonos
From Santorini, we took the high-speed ferry to Mykonos, where we spent three nights at the Myconian Villa Collection.
This part of the trip was especially valuable from a travel advisor perspective because I was able to see so many of the different Myconian properties.
And trust me, when you're looking at Mykonos hotels online, it can be difficult to understand how all of these properties differ.
We toured fourteen (!!!) Myconian Collection hotels in different areas of the island, including properties around Elia Beach, Agrari Beach, Platis Gialos, Ornos and Mykonos Town. We also managed to fit in lunch and some beach time at Almiriki Beach Club.
Seeing these properties in person gave me a much better understanding of which one I would choose for a couple, a family, someone who wants to be close to town or someone whose priority is spending their days at the beach.
That's the kind of information you simply don't get from looking at hotel photos online.
Mykonos Beyond the Beach Clubs
Of course, Mykonos is known for its beaches, restaurants and nightlife, but there is much more to the island. I loved experiencing both sides of Mykonos—the beautiful hotels, restaurants and beaches along with the history and culture.
Mykonos Town itself is exactly what you hope it will be: whitewashed buildings, blue accents, narrow winding streets and little shops and restaurants tucked around every corner.
It's definitely a destination where I recommend leaving some unstructured time. You don't need every minute planned. Part of the fun is wandering around and seeing where you end up.
And Then There Was Cyprus
After Mykonos, we flew to Cyprus for the final portion of the trip and checked into AMARA in Limassol for three nights.
Cyprus was the destination I knew the least about going into this trip—and probably the one I was most curious to experience.
AMARA is a beautiful luxury resort overlooking the Mediterranean and made a fantastic base for exploring the island. We also had the opportunity to experience several of the hotel's restaurants, including Beefbar, Ristorante Locatelli and Matsuhisa.
You definitely won't go hungry here!
But what I really loved was getting outside the resort and seeing how much more Cyprus has to offer.
Wine, Villages and a Different Side of Cyprus
One day took us into the countryside to Vlassides Winery, followed by the village of Omodos.
Omodos was exactly the kind of place I love discovering when I travel—cobblestone streets, local character and a much slower pace than the resort areas along the coast. We visited the village and Holy Cross Monastery before stopping for lunch and eventually returning to AMARA for some much-appreciated spa time.
Wine tasting, a beautiful village, local food and a spa treatment? That pretty much sums up my ideal travel day.
Exploring Paphos
Our final full day was devoted to exploring the western side of Cyprus.
We traveled toward Paphos, stopping along the way at Petra tou Romiou, traditionally known as the birthplace of Aphrodite, and visiting the Greco-Roman amphitheater at Kourion.
We continued into Paphos, toured the Elysium Hotel, had lunch and visited the Paphos mosaics before returning to Limassol.
It was a great reminder that Cyprus isn't simply a place to fly to, check into a resort and stay by the pool for a week. There is history, wine country, archaeological sites, traditional villages and a beautiful coastline to explore.
Greece or Cyprus? Why Not Both?
One of my biggest takeaways from this trip was how well Greece and Cyprus can complement one another.
Santorini gives you those dramatic caldera views and iconic Greek scenery. Mykonos brings beautiful beaches, fantastic hotels, restaurants and nightlife. And Cyprus adds another layer entirely—luxury resorts, wineries, villages, archaeological sites and a culture that feels both Mediterranean and distinctly its own.
The entire trip also reinforced something I say all the time: there is no substitute for experiencing a destination firsthand.
I toured the hotels. I rode the ferries. I took the flights between islands. I experienced the restaurants and beaches and traveled the distances between the resorts and the places clients actually want to see.
That allows me to do more than simply tell a client that a hotel is beautiful. I can help determine whether it's the right beautiful hotel for them.
And as for Athens?
Considering my delayed flight stole most of my time there, I think it's only fair that Greece and I schedule a rematch.
I guess I'll just have to go back!
Thinking about Greece or Cyprus? Let's create an itinerary that goes beyond simply checking the islands off your list.
