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About Personality Journeys
Personality Journeys is a luxury adventure travel operator based in Greece, specializing in tailor-made yachting and land-based tours in the best locations that Greece has to offer. We design from A to Z original multi-destination and multi-experience holidays for private groups, families, solo travellers, couples and corporate groups.
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Tours and Tickets by Personality Journeys

Sail the Greek Cyclades Islands

Other than Santorini, Mykonos, and Paros - which all boast international flights - many of the Greek Cyclades Islands go overlooked by travelers to Greece. On this five-day sailing adventure, discover three of the Cyclades Islands that most tours miss: Kea, Kythnos and Serifos. Escape the busy pace of life in Athens and enjoy an idyllic small group cruise through the Greek Mediterranean.
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5 days
from US$905.99

Mythical Peloponnese

Discover the hidden treasures of Greece in this action packed small group adventure. Hike above the tree line of the highest mountains in the Peloponnese and paddle around the turquoise waters of Mani peninsula. This is the perfect option for anyone looking for a holiday which combines the very best of the land and sea of Greece. Scale the heights of Mount Taygetus and explore Vyros Gorge amongst ancient Spartan trails. Take a boat-trip to one the most captivating caves in the world, then walk and swim around Cape Tenaro the stunningly scenic, southernmost point of mainland Europe.
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6 days
from US$1,590.11

Vouliagmeni walking and the Lake tour

Explore the Vouliagmeni Hills and swim in the Vouliagmeni Lake with this guided walking tour. You'll take a long walk through the hills, taking in views of the Saronic Gulf as your guide tells you about local history and culture. Onc eyou reach the lake, you'll have plenty of time to swim in warm thermal waters followed by lunch of fresh seafood at a local taverna.
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4 hours
from US$69.55

Sailing and Walking the Greek islands

Sail to the most unknown corners of stunning Cyclades Islands such as Kea, Kythnos, Syros and Serifos and walk in the footsteps of the ancients along beautiful trails, in this small group week-long sailing holiday. Choose one of the available departures and sail on top of the range boats which are navigated by qualified skippers eager to share their regional knowledge with you. Whether you’re an experienced sea and land adventurer or it’s your first time, you’ll enjoy a unique, multi-level experience in the Aegean Sea. Connect with like-minded travelers and learn the basics of sailing or simply kick back to bask in the sun whilst enjoying the caresses of the Aegean winds.
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8 days
from US$1,504.47
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Jacky wrote a review Sep 2019
Dallas, Texas1 contribution1 helpful vote
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. 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 felt right for our group. Dimitris informed us on everything that was going on throughout our booking and travel process, so there were no surprises along the way. He answered every question we had and made sure we were prepared when we arrived in Athens. Andreas went above and beyond in his role as our skipper for the week. He was patient and thoughtful with our group, and put so much effort into making sure we had the best trip possible. We felt very safe and protected throughout all of our travels, and were taken to some of the most incredible place – places that weren’t even on our initial itinerary. Andreas’ expertise in his craft and his companionate demeanor are the reasons our trip was as fantastic as it was. He exceeded all of our expectations and genuinely made this trip one of the best of our lives. Thank you, Dimitris and Andreas, for giving us a week we will never forget! We can honestly say we would not have had the same experience if it wasn't for all of your help and consideration.
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Date of experience: August 2019
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Response from DimZog, Owner at Personality Journeys
Responded 4 Sep 2019
Hello J! Thank you so much for your review we loved reading it and would be excited to have you again in Greece soon! Greetings to the team! Best wishes, Dimitris
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ahaway wrote a review Aug 2019
1 contribution
I was part of the mwdance 10 day tour group of 12. The trip was arranged for us according to our specific wishes and requirements. It was a fabulous trip with no hiccups! Thank you Dimitri.
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Date of experience: June 2019
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Maucca K wrote a review Aug 2019
Laren, The Netherlands2 contributions2 helpful votes
We enjoyed a private boat day with our family with Personality Journeys outside of Vouliagmeni. Lovely little secret places and beaches visited for swimming and a lunch close to the palace of Poseidon. RIB boat was a fun ride for all of us - young and old!
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Review collected in partnership with this attraction
Date of experience: August 2019
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mwdance wrote a review Jun 2019
Boston28 contributions10 helpful votes
Dimitri planned an excellent trip to Athens, ancient sites & islands Guides extremely knowledgeable Hotel locations perfect Transfers were always on time Thank You from our group of 12
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Date of experience: June 2019
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Venture24221391668 wrote a review Jun 2019
1 contribution
My wife, my daughter age 27, and my son age 22, and I had a truly memorable two week trip to Greece. The first five days were in Athens including a day trip to Delphi and the Byzantine church/monastery, Osios Lukas The second week was sailing on a 40 foot catamaran through the Cyclades islands (Mykonos, Paros, Antiparos, Naxos). We ferried to Santorini for the last two days Prior to our trip, our primary contact, Dimitris, was exceptionally responsive to our questions and provided useful information in a timely manner. He arranged our guide for Athens and Delphi and handled all the paperwork for chartering the catamaran. He made a point of meeting us in Athens where he answered additional questions and provided useful tips. During the cruise, he checked in by text several times to make sure all was well. Stephanie, our guide for a day in Athens and a day in Delphi, was on time, knowledgeable, and a pleasure to be with. She was attentive to our questions and was on top of all logistics. Our catamaran captain (a different Dimitris) could not have been better. Although relatively young, he was an extremely competent sailor who was constantly making sure that all aspects of the boat were functioning properly. He was a delightful, polite companion with a quiet sense of humor and a broad knowledge of the islands. Knowing that we preferred to sail (versus powering), he suggested itineraries that made sure that we got to the places we wanted to see while giving us the best opportunities to sail. He was particularly attentive to finding harbors/coves where we would be sheltered from wind and swells. He was always available yet never imposing on our time or space. The catamaran, a Lagoon 400, was surprisingly capacious and well thought out. We were grateful that Personality Journeys recommended a boat that included four separate cabins each with its own head. I am 6'5" and had no problem with headroom. There were several places in the stern for all four of us to comfortably relax as well as plenty of space on the bow to sunbathe, including stretching out on the netting between the two hulls. It is one of the few boats that I have sailed where all the equipment - from sailing and navigational equipment to stoves to electric toilets - all worked perfectly.
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Review collected in partnership with this attraction
Date of experience: June 2019
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