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
Over 10 days you will discover Greece's best islands, learn about ancient Greek mythologies, watch the sunset over Santorini during a cruise, and much more. The trip will start...
Two weeks is a great length for a Greek vacation. You'll have plenty of time to see multiple islands and historic mainland sites, taking part in cultural or outdoor activities...
Spending a week in Greece is already great—but with an added bonus day, you have another chance to dig into the food, culture, and outdoor activities that make this destination...
Family itineraries
With a week to spend, you and your family can find plenty of ways to explore Greece. Whether you want to hit the highlights with interactive tours in Athens and Santorini, get...
Two weeks gives you and your family plenty of time to traverse the nearly 1,000 miles of coastline that Greece has to offer. Whether you're going for a deep dive into the...
Bring the whole family for 13 days of exploring the ABCs of Crete with this itinerary. After discovering the myths of the Acropolis in Athens, you'll fly to Greece's largest...
Luxury itineraries
Ten days in Greece is an excellent amount of time to delve into a highlights tour that features Athens, Crete, and three picturesque Cyclades islands. You can also cater the...
Greece and luxury go hand in hand, and with one week to explore, you can hop between the mainland and one or two islands. Athens is a natural starting point for most tours,...
Road trip itineraries
Take a drive through the scenery and history of mainland Greece with this 17-day itinerary. Begin in Athens, then make your way through the seaside towns, vineyards, scenic...
Take a week to drive through the mythological territory of mainland Greece with this itinerary. Your seven days will start and end in Athens, covering the historical sites and...
Honeymoon itineraries
Recent trip reviews for Penny
Fabulous 50 in Greece
Greece
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Apr 1 - Apr 15, 2026
We decided to travel in the shoulder season over Easter and Greek Orthodox Easter and Penny made sure the places we visited were open and ready for... Read more
