Penny Vasileiadi
I’m Penny, a Travel Specialist from Kalamata. I grew up among olive groves in the Peloponnese, and that close connection to local life still shapes the way I plan trips today. With a degree in History and Archaeology, I love weaving Greece’s stories, ancient and modern, into each itinerary, pairing must-see highlights with authentic experiences, warm hospitality, and the kind of places you’d never find without a local.
What places and activities do you specialize in?
"I specialize in travel throughout Greece, designing tailor-made itineraries that balance the iconic highlights with places that feel genuinely local. I’m especially drawn to experiences that connect travelers to the country’s culture and everyday life, whether that’s wandering historic neighborhoods, slowing down in traditional villages, or discovering landscapes that most visitors miss. The activities I love planning most include cultural experiences like museums and archaeological sites—brought to life through history, mythology, and storytelling—along with food-focused moments such as market visits, cooking classes, wine tastings, and olive oil tastings. I also enjoy creating routes that mix scenic drives, beach time, and nature outings, from gentle walks to more adventurous hikes, always shaped around each traveler’s interests and pace."
How did you get involved in travel?
"I got involved in travel naturally, through my family’s restaurant in Kalamata. From a young age I met visitors from all over the world, helped with recommendations, and saw how much a local tip or a good story could transform someone’s experience. I also love traveling myself, especially exploring new cities, so I understand the excitement of discovering a place for the first time. That’s why it gives me real pleasure to help others explore Greece, beyond the guidebook, with experiences that feel authentic and personal. Later, my studies in History and Archaeology deepened that passion and gave me even more ways to bring destinations to life through culture, heritage, and storytelling."
Please share a unique travel experience you will never forget.
"Although Greece will always have a special place in my heart, one travel experience I’ll never forget was visiting the Vatican Museums and the Sistine Chapel for the first time. Walking through the galleries and then stepping into the chapel felt almost unreal. Suddenly, I was surrounded by centuries of history, symbolism, and artistic mastery. I remember looking up and getting completely lost in the details of Michelangelo’s frescoes, realizing that no photo can prepare you for the scale and emotion of it in person. "
Penny's favorite itineraries and travel advice
Top itineraries and travel advice
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