Tailor Made Holidays in Greece
designed by local experts

Plan Your Trip

What are you looking for?

Local Experts

We are local travel specialists with pure knowledge of Greece’s best destinations

Real Partnerships

We have been exploring Greece and the world since childhood and we have turned our passion into a profession

Tailor Made Experience

We are at your disposal to suggest, organize and create unforgettable moments in Greece for you

How it works

See the quick process on how to plan your travel with Personality Journeys

Step 1

Tell us what you have
in mind

Fill a quick travel form with some basic information and details about your desired trip.

Step 2

Connect with our
travel expert

Our travel experts, are locals with extended knowledge in every
destination we offer.

Step 3

Book your trip

We offer multiple and completely
secure payment methods, for your
own convenience.

Plan your trip

Choose your desirable trip style and explore the beauties of Greece!

Sailing Adventures

Experience a sailing adventure crafted by our experts!

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Family Holidays

Live your perfect family holidays in Greece!

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Take your better half in a lifetime experience!

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Religious & Spiritual Trips

Connect with the higher force in iconic sites.

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Hiking Greece

Beautiful nature pathways waiting to be explored!

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History & Culture

Discover Greece's rich history and culture...

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Find your inner peace and wellness in Greece.

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Reviews by previous travelers


Exceeded all Expectations!

We had the most exceptional travel experience with Personality Journeys. Both our travel agent and out travel guide (“skipper”) were fantastic! Dimitris was everything we could have looked for in a travel agent....


10th Anniversary and Honey Moon!

This was our first overseas trip ever and it turned out amazing! Dimitris planned our trip out within our budget and the lodging was fantastic. Our favorite hotel was the Corfos Bay Hotel in Mykonos for its genuine beauty and true Island architecture. All of our ferry…

Jacky Merianos

Sail the Cyclades islands 5 days

Dimitris was everything we could have looked for in a travel agent. Following the parameters we laid out for him, he provided us with the absolute best options for our travels. He was both honest and patient with us, and made sure we took as much time as we needed to finalize a trip that...


perfect week!

Dimitris organized a private sail and hike trip for us. Everything was perfectly planned. Dimitris made us feel safe at all time as he was always in contact. He met us for one of the hikes , which was wonderful. Socrates, our captain and Savy his assistant, were so kind to us...

Inspiration Get inspired by our articles for your next trip in Greece

Top reasons to choose a sailing holiday over hotel accommodation

Top reasons to choose a sailing holiday over hotel accommodation

When you choose to charter a yacht for your Greek holiday, you are not only choosing a mode of transportation or a place to sleep, but you are booking an unparalleled experience. Imagine waking up every morning in a different location...

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Honeymoon & vows renewal holidays in Greece

Honeymoon & vows renewal holidays in Greece

With its scores of gorgeous islands, intriguing cultural attractions, amazing beaches, and delicious food, it’s easy to see why Greece remains a much sought-after honeymoon...

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Hiking the caldera of Santorini experience

Hiking the caldera of Santorini experience

Walking from Fira to Oia with an expert local guide is undoubtedly the most authentic way to experience Santorini’s stunning caldera away from mainstream choices and...

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Plan your trip

with Personality Journeys

In 3 easy steps you can plan your dream vacations in Greece
tailored by local experts!