Where do I begin? From the very start of the ...

Greece | May 5 - May 15, 2026

Where do I begin? From the very start of the planning process to the ten wonderful days we spent in Greece, Sydney was incredible. She took the information we shared about what we wanted to see and do and turned it into a spectacular vacation. Every detail was thoughtfully arranged, making it easy for us to enjoy each day—whether we were meeting a guide or wandering through the towns on our own.

What stood out most was how personalized everything felt. Sydney truly listened to what we wanted and created an itinerary that perfectly matched our interests. From the activities to the pacing of the trip, it was clear that every choice had been made with care.

Each day unfolded seamlessly, with the perfect balance of guided experiences and free time to explore independently. We never felt rushed, yet we were able to see and do so much. Sydney’s organization and attention to detail made the trip completely stress-free, allowing us to simply enjoy every moment.

We began with a fabulous Evening Neighborhood Food Walk with Katerina of Greek Travel Tellers. This was our introduction to Athens and to Greece, and Katerina warmly welcomed us to her city. We sampled food and drinks from five different establishments while learning about the history, culture, and everyday life of Athens. It was the perfect way to begin our trip and immediately made us feel connected to the city.

Another standout experience was our day on Hydra with our guide, Elizabeth of Alternative Athens. Her knowledge of the island, combined with her warm personality and easygoing demeanor, made it feel as though we were wandering the town with an old friend. By the end of our time together, we wished we could meet her again the next morning for coffee.

We also thoroughly enjoyed our hike with Dimitrius of Yummy Pedals on the island of Mykonos. We walked along donkey trails and countryside footpaths, stopping at a small church in the middle of a field. Dimitrius explained that these churches, scattered outside of town, are family churches used for special celebrations and occasions. We continued to a peaceful beach, where we cooled our feet in the water while enjoying homemade lemonade and a local pastry specialty.

On Naxos, we took a bike ride with Manos of Aurelia e-Assist Bikes through the island’s rural countryside. Along the way, we visited an archaeological site, learned about agricultural traditions, toured a farm producing cheese using traditional methods, and stopped at an olive mill museum to taste local olive oils and olives. Afterwards, we enjoyed a light farm-to-table lunch featuring cheeses made on the farm, fresh produce, and local wine before returning to Naxos Town.

After a short rest, we joined a group for the Mythology Sunset Walk and Wines of Naxos, led by Elizabeth of Naxos Cultural Tours. Elizabeth described herself as a “mythology junkie,” and by the end of the tour, she had nearly made us mythology enthusiasts as well. She brought stories of gods such as Odysseus and Poseidon to life as we wandered through the streets of Naxos Town, ending in the medieval castle district, once home to the acropolis. We then enjoyed a wine tasting in honor of Dionysus, the god of wine, before concluding at the Portara—the gate of the Temple of Apollo—where we watched a picture-perfect sunset.

Our time on Santorini included a hike down the famous Karavolades Stairs—all 588 of them—which connect the Old Port of Fira to the clifftop town above. We made it down much faster than we made it back up and rewarded ourselves with gelato to celebrate the climb. We also hiked to Skaros Rock, a dramatic promontory on the Aegean side of the island that was once the site of a castle and later served as a gathering place for the Christian community until an earthquake in the 19th century destroyed the structure.

One of my favorite things to do while traveling is take a cooking class, and our class on Santorini did not disappoint. We visited a local winery, where we learned about the indigenous grape varieties that thrive in the volcanic soil and sampled several island wines. Our cooking class was led by Chef Chris of Artemis Karamolegos Winery, who guided us through the hands-on preparation of traditional dishes. I can’t wait to recreate them for friends at home.

Our final outing of the trip was a sunset catamaran cruise. We stopped at Mesa Pigadia and Red Beach for swimming and snorkeling and enjoyed a delicious Greek barbecue while watching a breathtaking sunset. It was the perfect ending to an unforgettable journey.

While we did much more than what I have shared here, these were the activities we enjoyed the most.

Greece was truly unforgettable, and Sydney played a huge role in making it such a special experience. I would highly recommend her to anyone looking for a beautifully planned and memorable vacation.