Santorini is the glittering gem of the Cyclades. You'll spend five days exploring this iconic Greek island from top to bottom with beach time, volcano tours, and sunsets that'll take your breath away. Then ferry to neighboring Folegandros to relax on a smaller and lesser-visited (but no less beautiful) island, discovering empty coastline and medieval architecture before returning to Santorini for your departure.
Personality Journeys Greece
Here at Personality Journeys, we love to travel, discover, and share. Personality Journeys is an adventure travel operator specializing in active, experiential travel in the best locations that Greece has to offer. We design transformative, original multi-destination and multi-experience adventures that suit the personality of our discerning travelers. We visualize and execute scheduled and tailor-made journeys for small groups of friends, families, solo travelers, couples and corporate groups.
HYBA (Hellenic Yacht Brokers Association)
ATTA (Adventure Travel Trade Association)
HATTA (Hellenic Association of Travel Agents)
HIKERS FRIENDLY (Association of Greek walking tours operators)
ACCREDITED /LICENCED BY:
GNTO (Greek National Tourism Organization)
Featured trips & expertise
Many travelers flock to Santorini and Mykonos, but during this trip, you'll visit two spectacular yet less-traveled islands in the Cyclades chain. Start off in Paros, where golden sand beaches and charming villages are yours to explore. Then hop a ferry to neighboring Naxos for a bustling Chora (main town), beautiful whitewashed villages clinging to mountainsides, and countryside filled with churches, archaeological sites, and local distilleries.
Visit the world-renowned sea sports paradise of Paros and Naxos islands for 8 days of oceanside hikes, windsurfing, and stand-up paddleboarding. And when you're not taking on all the active adventures the islands have to offer? Explore the unique local architecture, delectable cuisine, cosmopolitan nightlife, and impressive archaeological sites.
Discover Greece's hidden treasures on this action-packed adventure. Hike the tallest mountains in the Peloponnese, paddle the beautiful Mani Peninsula, and scale the heights of ancient Sparta's Mount Taygetus. Complete your trip with a swim at the southernmost point of mainland Europe.
See some of Greece's star attractions on this 12-day itinerary. Start off in the capital of Athens and experience its rich historic heritage and modern food scene. Then ship out to the Cyclades, home to Mykonos and Santorini, where you'll enjoy beaches, archaeological tours, and all the fresh seafood your stomach could desire.
Cruise like a celebrity through the glittering waters of the Cyclades on this nine-day itinerary. The Cyclades are some of the most quintessential Greek islands, and you'll see seven of them from the decks of your yacht, along with plenty of time to explore onshore. From lesser-known spots like beach-lined Milos and petite Antiparos to favorites like bustling Naxos and cosmopolitan Mykonos, you'll scope out this island chain in style.
Recent Trip Reviews for Personality Journeys Greece
Trip to greece, Greece - Jul 29 - Aug 6, 2019
Dimitris was such an excellent resource. I had many questions and emailed him A LOT. Every time I asked about my trip, Dimitris he always got back to me immediately with a reply. He was so helpful before and during our trip. We were 100% satisfied with his service.
When we arrived in Athens, our itinerary was a little tough at first. Since we arrived on a red-eye flight only sleeping a few hours, the morning/afternoon tour of the Acropolis grounds and museum was a little long for us,... read more
Bchlorette party , Greece - Aug 3 - Aug 10, 2019
It was a phenomenal trip—thank you, Dmitris for all of your planning, and Andreas absolutely made our trip! We got so insanely lucky with you guys. ❤️
Bchlorette party , Greece - Aug 3 - Aug 10, 2019
We had the most exceptional experience with kimkim. Upon entering the details of our desired travels, we were immediately connected with an agent, Dimtiris, who assisted us in planning the trip of a lifetime.
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... read more
Custom island / boat/ touring . we want to experience greece particularly some beaches old towns island etc. we are open to suggestions., Greece - Jul 29 - Aug 5, 2019
Stelios was excellent. He engaged my wife, sister and children in a very positive thoughtful way. Our food was excellent and our chef was fantastic. All above expectations. Highly recommend this trip
Trip to greece, Greece - Jul 26 - Aug 3, 2019
Our Greece vacation was everything we had hoped it would be. Beautiful locations and great food. Our guide dimitris for acropolis was extremely knowledgeable and a pleasure. Naxos sailing was wonderful. And our guide for kayaking was both safety conscious and very comical in his approach. Maria was an excellent hiking tour guide on santorini where she took us to a fabulous sunset view and also surprised us with food and drink for the magic moment. Dimitris and Kimkim was very responsive... read more
Beautiful greece, Greece - May 11 - Jun 1, 2019
Dimitris did an excellent job of combining my ideas with his knowledge of Greece. This was my
third time to Greece so there were areas I wanted to revisit and of course have new experiences. Dimitris incorporated some exciting adventures into our vacation. Meteora, Olympia & Monemvasia are a must see. To relax after two weeks of our cross country drive we relaxed at his suggestion in a wonderful Villa on Naxos. Dimitris was patient and always available for questions and quickly resolved... read more
Trip to greece, Greece - Jun 16 - Jun 28, 2019
Overall Dimitris did a great job in helping us plan our family Greece trip. With so many amazing sites to see and islands to visit, it can be overwhelming knowing what would be good for our family and Dimitris took care of everything. We communicated through the trip and he quickly answered any/all questions that I had. We even met him in Athens and he handed us our ferry tickets and helped us buy an extra ticket that we needed when one of my kids joined us at the last minute.
We were... read more
Adventure food relax, Greece - May 23 - Jun 10, 2019
Overall our trip to Greece was wonderful! Dimitris was very responsive during our planning phase and while we were there. He put together a good itinerary that included accommodations, travel to/from islands, tours based on what we like, car rental and a driver to pick us up during our travels. (The driver, Stavos made our trip particularly enjoyable as he drove us to various sites as part of our journey. He was very knowledgeable and so kind.) Dimitris recommended a smaller less inhabited... read more
Trip to greece, Greece - May 29 - Jun 6, 2019
Our trip to Greece exceeded my expectations. From the first interactions with kimkim I was very pleased as I was having difficulty finding a good balance between relaxation, luxury and adventure from one source. The initial survey made me feel I finally found a source that understood that there was more than a single goal in vacation planning. With limited time available, Dimitris with Personality Journeys was able to fit all three goals into a 9-day tip with a one-month lead time. With... read more
Trip to greece, Greece - May 11 - May 24, 2019
We had an Amazing Trip. Dimitris did a great job with our itinerary and when we made some last minute changes he had great advice and helped us switch around our reservations. The Boat Charter was Amazing. The only negative would be the Hotel room for the first few nights in Athens. the room had 3 very small single beds. but at the end of the trip we stayed at the same hotel and got a better room with a real bed. The Rest of the Hotels were amazing and Greece is beautiful.
10th anniversary honeymoon, Greece - May 22 - May 30, 2019
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 transportation was booked for us and spot on. The private transfer on our second day via Mr. Stavros was perfect, he even took the time to show us around Athens as we had extra time before the ferry departed. Dimitris... read more
Trip to greece, Greece - Apr 8 - Apr 14, 2019
We only had a few days available in Greece at the end of a four and a half month trip around the world and we wanted them to be special but fairly restful and Dimitris made the perfect plan for us. We were picked up at the airport by Stavros, who had bottled water, candies and a tour map ready for us. He was part taxi driver and part tour guide, telling us about the city as he drove us to our airbnb. We then had a few days to explore the city on our own. Dimitris would have arranged tours for... read more
Graduation teip, Greece - Aug 12 - Aug 20, 2018
We had a wonderful experience. Dimitris was very helpful and created a great itinerary for our vacation.
Land tour of greece, Greece - Jul 5 - Jul 9, 2018
Dimitris was very responsive and planned a trip for me that was a true reflection of my desired experience. I had to make some last minute changes due to a weather-related missed flight and Dimitris dealt with things quickly and capably.