Samantha’s OWR Greece Odyssey: The Trip That Was Worth the Wait

Greece had been calling Samantha’s name for years — and this time, she finally picked up.

What followed was eight days of island-hopping, laughter, and new friendships that made the trip way more than just another holiday.

You could say my journey to Greece is not completely dissimilar to Odysseus’ journey home after the Trojan War (well actually not at all, but I had to squeeze a Homer reference in here, how could you not?). I’ve wanted to visit Greece for as long as I can remember, but it just never seemed to work out for various reasons: I wasn’t in the right place financially, I wasn’t confident enough to travel to such a different country on my own, I was waiting for the right group of friends to want to go with me, etc. Even when I did a study abroad in college in Aix-en-Provence, France, it didn’t feel like the right time for Greece.

In late spring 2025, I decided I wanted to take some time for myself and go on a trip to Central America (we’ll get to Greece, don’t worry). I searched online for different resorts, and found a few I liked. I figured a week at a coastal resort with mostly beach time would be a great way to recharge and disconnect in a low pressure way. Then I looked at the weather for my intended travel window: not the best time to be in Central America. Still dedicated to taking the time to travel, I started thinking about going to Europe instead. I thought about staying at a resort and just relaxing, but it just didn’t feel right for Europe. I began researching different, popular solo traveler groups (like Intrepid, G Adventures, Flash Pack, etc.).

They all had solid itineraries in incredible places, but they seemed a little, not corporate, but they didn’t have that personal touch that traveling on your own inherently has. When I studied abroad, it was a very small university in a smaller city, so I really got to immerse myself in the culture and got to know almost all of the other study abroad students, which really added to my experience. I wanted that level of immersion, and I wanted to go with people that appreciated it, too.

“I STUMBLED UPON OTHER WAY ROUND, AND SOMETHING CLICKED”

I stumbled upon Other Way Round, and something clicked. Looking through their itineraries, seeing the photos, how the descriptions were written with a focus on immersion and experiencing the real culture, and seeing Steve in many of the photos from different trips made it seem like THIS company really cared about putting together a fantastic trip and making sure the people that travel with them felt how genuinely they meant it. The age range was also perfect, and their “Travel Style” lined up with everything I was looking for. I saw their Greece itinerary, and compared to the others I was considering, OWR’s was by far the the best: Athens for history, Paros for chill island life while embracing the local culture, and then Santorini for the incredible views and the sea. This could be the right time for Greece, this itinerary, with this company. My only concern? How does ANY company in 2025 not have at least one bad review?? Every review I found raved about OWR and their trip, no negative comments, nothing. I decided to reach out directly to OWR, and Steve actually emailed me back! He responded at length with thoughtful, considered responses, and he made me feel like he saw me as a fellow traveler and not just a number. After a few exchanges back and forth (I am a planner, so I had many, many questions, and Steve was kind and patient enough to answer them all!), I decided to take the plunge: Greece in September 2025. Finally, I was going!!

Since I had a few months to prep, I started walking more to prep for all those Greek steps, downloaded Duolingo to attempt to learn some Greek, and watched “Mama Mia” probably 3-4 times (possibly more, don’t judge!). I would consider myself a plus-size person, so I wanted to make sure I didn’t hold anyone up by being too out of shape, and I wanted to build some confidence in myself and know that while I am a “lazy American,” at least I can get myself where I need to go without looking like one! I ordered too many new clothes, multiple pairs of shoes to find the magical pair that would keep my feet pain free (Tevas Hurricane sandals were PERFECT), and new luggage. I was excited all summer, counting the days until my dream trip. When the week finally arrived, so did the nerves. Who would be in my group? Would we get along? Is the vibe going to be as good as I’ve built up in my mind? Would my roommate and I get along? And of course, would all of my flights be on time??

Thankfully, both of my flights were on time with zero issues, and I managed to catch some sleep on my red eye. When I arrived, it was a little chaotic being in a new, unfamiliar country after nearly 12 hours of travel, but I found my driver and got to my hotel (just under an hour ride). I was there before my roommate, but our room wasn’t ready quite yet. I messaged another person in the group (Hi, Jill!) who had a similar arrival time, and we ended up meeting up for a bit while we waited for our rooms. After a stop at the pharmacy across the street from The Gem Society to grab some sunscreen, it was time to check in, shower, and then get ready for our welcome dinner. My roommate arrived shortly after me (Hi, Brittany!!), and we clicked pretty easily. After some downtime where we did our own thing, we got ready and then headed down to meet our leader and the rest of our group. It was time for my trip to Greece to officially begin!

“AT NO POINT DURING OUR 8 DAYS DID I EVER FEEL UNCOMFORTABLE, HAVE ANY AWKWARD SILENCES, OR FEEL JUDGED”

Our Group & Our Leader

I would say everyone in our group meshed really well. There were definitely some different personalities, extroverts, introverts, ambiverts all. There were 11 of us, all from the U.S. except for 1 (Hi, Priyanka!) from Switzerland/India. Everyone had a very open energy, positive vibes, and at no point during our 8 days did I ever feel uncomfortable, have any awkward silences, or feel judged even though we came from all over the country and had very different backgrounds. Everyone wanted to just have an amazing time in an amazing place, so why not be amazing people?

Our leader, Aris – what an incredible, wonderful human being. He immediately made you feel welcome and part of the group, taught us SO much about the Greek people, the REAL Greek people and culture, and was fully present and dedicated to making sure our trip was as magical as possible. Even when the weather (winds) caused our itinerary to change, Aris handled everything so seamlessly, it felt like this was how the trip was always meant to have been. Efcharisto, Aris!! You made this trip truly a dream come true.

The Food & The Greek People

When I say that the food in Greece is next level, believe it – I’ve been home for almost a week, and nothing will ever be as good as what I ate while there. Greek salads with every meal, the chickpeas, the beans, the souvlaki, the saganaki, the olives, the feta, even the bread – everything was incredible. Every restaurant we ate at as a group was incredible, all of the included meals were more than generous (when you think they couldn’t possibly bring out more food, they can and they will!), and the service was amazing. Petra Farms on Paros was absolutely a food highlight – the meal we had there was exceptional, I’m still dreaming about the Greek salad and the chickpeas they served us!

Greek hospitality is NOT a myth – every local we interacted with was just the warmest and most welcoming, and the guides we met all went above and beyond to make sure we had the time of our lives. All of the hotel staff also made us feel more than welcome, and the hotel rooms were all comfortable, spacious enough for two strangers, and had great views. Never did it feel like we were “just another group of loud tourists,” it genuinely felt like Greece welcomed us with open arms to experience all the joy and peace the country has to offer.

“ONE OF THE NICEST THINGS ABOUT THIS TRIP WAS THAT ONCE WE GOT THERE, YOU DID NOT HAVE TO MAKE ANY BIG DECISIONS ASIDE FROM WHAT TO DRINK AND WHAT TO ORDER OUTSIDE OF OUR GROUP MEALS”

The Trip Itself

One of the nicest things about this trip was that once we got there, you did not have to make any big decisions aside from what to drink and what to order outside of our group meals, plus a few of the Free Day activities. All the transportation and coordination was taken care of (thanks to OWR & Aris)! My personal favorite days/activities were the  Acropolis and full day in Athens (definitely visit the Acropolis Museum – I wish I had spent more time here and less at the Archaeology Museum), and our catamaran day in Santorini.

Our guide for the Acropolis, Martina, was incredibly knowledgeable and very game for questions and just being a part of the group. You don’t realize how much being around people of the same age affects the dynamics, but it really helps make the experience special. We walked the Acropolis (it is not as difficult to get up there as the internet would have you believe – I was genuinely worried I’d struggle, but the route we went took 5-10 minutes and then all of a sudden, you’re at the gate!) and then down through a bit of Athens to Monastiraki Square with her, and she had fun tidbits of information to share the whole way.

After our included group lunch, my roommate and I decided to check out the Archaeology Museum, each got a massage back at the hotel (much needed and completely worth it!), and then went to the Acropolis Museum before eating dinner below the Acropolis. It was a perfect day filled with ancient history and just soaking in the wonder that is Athens.

On Paros, we visited Petra Farms for one of the best meals of the trip, met Theo and his cat Chico who showed us around the farm, watched Aris make friends with their chickens, and took in the breathtaking views from their balcony. It was a perfect way to start our time on Paros.

The rest of the time here was spent exploring Naousa and swimming in the Aegean near Parikia, and I highly recommend using sunscreen even while swimming (learned the hard way the the sea does not protect you from the Greek sun!). If you’re a cat lover like me, you’ll love Paros – I saw the most cats here, and our hotel, Mr. & Mrs. White, even had an unofficial hotel cat who we named Bagheera Selena/Midnight! Paros was the most laid back part of the trip, which was perfect after the hustle and bustle of Athens.

“THE COOKING CLASS WAS ABSOLUTELY ANOTHER HIGHLIGHT”

Our final stop, Santorini, was beautiful. I never appreciated it being a volcanic island until we were riding in our transfer up the steep, winding cliffs to get to our hotel in Kamari. The views here are stunning – no matter where you are, there are cliffs or sea or beautiful white buildings all surrounded by the clearest skies. Right from the ferry, we dropped off our stuff at the hotel and headed to our catamaran. This was one of my absolutely favorite parts of the trip. Our crew, Minos, Eva, and Kostas, were all incredible people and amazing cooks! We stopped to swim in a couple spots, including right near the volcano itself, and then had the most amazing meal prepared by the crew before we sailed back towards the port to watch the sunset.

A perfect Greek day I’ll remember forever. A part of me is still floating in the Aegean next to the volcano! There were some optional activities on Santorini, of which I opted to do both: kayaking in the Aegean and a cooking class at a local winery. The kayaking was beautiful, getting up close to the beaches and cliffs we sailed past the day before, and our guides were incredible once again! The cooking class was absolutely another highlight, but make sure you go hungry: we tasted as we cooked, but then they served us a whole meal afterwards! Every bite was divine, and I am absolutely looking forward to replicating it here at home!

We did of course visit Oia and Fira, which are both beautiful towns, and we lucked out: due to the winds, the cruise ship guests weren’t able to get onto the island, so both towns were much less busy than they typically would be. Our farewell dinner in Fira was next level, from the salad to the appetizers to the main meal (I am still dreaming of the beetroot risotto!), and we all got photos with the caldera as our backdrop thanks to our official photographer/leader, Aris!

“IT WAS  EVIDENT AT EVERY POINT THAT THE TRIP WAS DESIGNED BY PEOPLE WHO GENUINELY CARED, AND I NEVER HAD A WORRY, FELT ANY STRESS, ANXIETY, OR ANY FRUSTRATIONS FOR A PERFECT, MAGICAL, AND FULL 8 DAYS”

My Advice

If you made it this far, BOOK THE TRIP! This trip will stay with me forever: the places, the people, the magic of Greece definitely touched my soul, and I am already dreaming of when I can return and drink it all in again. You will not be disappointed in how OWR operates or the people they hire. Our leader, Aris, again was absolutely incredible, and every guide and driver we had throughout the trip was genuine and amazing.

It was evident at every point that the trip was designed by people who genuinely cared, and I never had a worry, felt any stress, anxiety, or any frustrations for a perfect, magical, and full 8 days. This company has only 5-star reviews for a reason: they more than deserve it! Treat yourself, and book your trip to Greece with OWR. It will be one of those experiences you dream about for the rest of your life, and it’s a trip you’ll wish you could experience for the first time all over again.

Efcharisto OWR for this magical journey. I cannot wait to book my next trip!!