Jessica’s OWR Greece Story: A Dream Trip, Finally Realised

 Jessica had always dreamed of visiting Greece but she wanted to save it for something special. Then one day, she decided to stop waiting.

At 36, she booked her dream trip to Greece with OWR and turned what was once a “someday” plan one of the best decisions ever.

● Why did you book the trip?

As a lover of ancient history and beautiful islands/beaches, Greece has always been my dream travel destination; but I wanted to save it for something special, such as a romantic honeymoon or a milestone birthday with loved ones. However, I found myself still single at 36 and with friends who were busy with their own families and could not go on a casual “girls trip” across the world. 2025 has been my “YOLO” year and I decided that I finally needed to make my dream trip to Greece happen no matter what. 

I was no stranger to solo group travel, having taken several trips with various other tour organizers, but had aged out of those catering to 18-20 somethings and after accidentally finding myself on a hiking tour with all 60-70 year olds last year, I was hesitant to book one with an organizer that catered to all ages. I had no idea a tour organizer specifically for 30-40s existed but randomly stumbled upon Other Way Round via Google search and knew that I had found the right company for my dream vacation. 

“KNOWING EVERYTHING WAS TAKEN CARE OF BY OWR MADE ME MUCH MORE AT EASE LEADING UP TO THE TRIP AND IT WAS SUCH A RELIEF NOT TO HAVE TO DO ANY EXNETSIVE PLANNING”

● How did you feel as the trip approached?

I found myself crying tears of joy multiple times prior to the trip. I had to pinch myself as I could not believe I was finally going to Greece. While traveling is always stressful, knowing everything was taken care of by OWR made me feel much more at ease leading up to the trip and it was such a relief not to have to do any extensive planning. The excitement grew as OWR began sending more detailed information a couple weeks prior to the trip and when they connected our group via WhatsApp a couple days before.

“SEEING THE ACROPOLIS FOR THE FIRST TIME ALL LIT UP WAS INDESCRIBABLE”

● How did you feel upon arrival?

I was exhausted after traveling for over 24 hours and arriving late at night but once again, was at ease knowing OWR had arranged a transfer service, with a friendly driver who was waiting for me upon arrival. Driving into Athens and seeing the Acropolis for the first time all lit up was indescribable and had me itching to get out early and explore the next day prior to meeting up with the group for dinner. I ended up wandering around the city all day, walking over 10 miles to see the Panathenaic Stadium, Temple of Olympian Zeus, Athens National Garden, and Lycabettus Hill. 

“OUR TOUR LEADER, ARIS, COULD NOT HAVE BEEN MORE AMAZING. HE WAS WITHIN OUR AGE GROUP AND IT FELT LIKE A FRIEND SHOWING US HIS HOME COUNTRY RATHER THAN A GUIDE”

● How were the people you travelled with? And the tour leader?

Our group consisted of 11 people – 10 from the United States and 1 from Switzerland, 10 women and 1 man. The conversation flowed over an amazing meal and wine at our first group dinner in Athens and several of us ended up finding ourselves at a nearby bar afterward to get to know each other even better. While the entire group got along well and often spent our time together as a group of 11, it was wonderful to see deeper connections form in smaller pairs and groups. I personally found myself drawn to 3 others who I ended up spending much of my free time with throughout the trip. Just a couple days in, and I felt like I was traveling with close friends from home vs people who were total strangers. One week later and we are still messaging each other daily and planning our next trip together with OWR. 

Our tour leader, Aris, could not have been more amazing. He was within our age group and it felt like a friend showing us his home country rather than a guide. It was apparent Aris loves Greece and wanted to show it to us in the most authentic and responsible way possible. He remained professional throughout the trip, but also was playful and joined in our inside jokes. He worked tirelessly and calmly to ensure we were happy when some of our planned activities needed to change at the last minute due to inclement weather and overall, provided us with an even better trip than we imagined. He clearly loves what he does and I am hopeful a Crete trip will one day be added so I can travel with him again. 

“ALL 3 HOTELS WERE WONDERFUL — CLEAN, SAFE, QUIET, AND COMFORTABLE”

● The hotels

All 3 hotels were wonderful – clean, safe, quiet, and comfortable. The Gem Society in Athens was within close proximity to many of the sights and popular neighborhoods, and Mr and Mrs White in Paros and Mar N Mar in Santorini were walking distance to the beach and shops/restaurants. Each hotel offered a delicious complimentary breakfast and offered amenities such as a pool and spa. Some group members even received rooms with private hot tubs at one of the hotels! The front desk staff and porters were all very welcoming and accommodating when it came to getting our rooms ready early, carrying large suitcases up and down the stairs, and offering recommendations. 

● The food

As a vegetarian (especially one who dislikes vegetables – I know, I know), it’s always a bit stressful going somewhere new and not knowing if your dietary requirements will be met while also not having to miss out on authentic foods. However, Aris was on top of it and ensured everything from the to-go breakfast boxes to our shared group dinners were not only vegetarian friendly but authentic and delicious. Between all the cheeses, spanakopita, beet risotto, souvlaki/gyro wraps, tomato and zucchini fritters, dolmas, veggie moussaka, and more, the food was better than I imagined and I find myself still having cravings for it a week later. 

● The places/activities

Prior to the tour, I was most excited to visit Athens to see the Acropolis and I could not wait for our guided tour on the 2nd day of the trip. While it was still quite crowded with tourists despite it being September, Aris and our guide expertly led us through the ruins while teaching us about the amazing sights we were seeing and helping us capture the best photo ops. Afterward, several of us made our way to a rooftop bar where we shared drinks while gazing out at the most incredible view of the Acropolis, which was almost more surreal than seeing it up close. 

In Paros, we had the opportunity to visit an organic farm where we received a wonderful tour of the grounds, including the crops and animals. We were then welcomed into the family home where we enjoyed a delicious homemade lunch and wine on the deck with the most breathtaking views of the sea. 

Our first catamaran ride was cancelled due to strong winds, but Aris prepared quickly a special alternate activity for us that included renting out loungers at a “beach club” in Paros where we had the opportunity to lay out, drink, and swim all day before having yet another amazing meal at a restaurant on the beach together. Aris mentioned this was a place he frequents with his friends, which made it feel even more special and authentic. 

“WHILE OPTIONAL, OUR ENTIRE GROUP OPTED TO DO THE COOKING CLASS/WINE TASTING EXCURSION IN SANTORINI AND IT WAS AN INCREDIBLE EXPERIENCE TO COLLABORATIVELY MAKE A MEAL AND THEN GET TO SIT DOWN AND ENJOY IT TOGETHER”

While optional, our entire group opted to do the cooking class/wine tasting excursion in Santorini and it was an incredible experience to collaboratively make a meal and then get to sit down and enjoy it together. I personally do not enjoy cooking and initially only came along for the wine tasting portion, but the cooking class actually ended up being the best part of the night thanks to the hilarious local chef who made our time in the kitchen a blast while also teaching us multiple recipes.

After the Acropolis, the sunset catamaran in Santorini was next on my list for activities I was most excited about, and it did not disappoint. The crew took great care of us from the moment we got onboard, ensuring we always had a glass of wine and/or beer in hand while we got to lay out and relax. There were a few stops throughout the ride where we had the opportunity to get out and swim in the beautiful blue waters of the Aegean Sea, which even an unconfident swimmer such as myself could not resist. All the while, the staff was cooking up a delicious meal for us including special vegetarian options just for me, which we then sat and enjoyed together as we watched the sun go down.

● Any little memorable moments along the way

-Hiking the Thira to Oia trail early in the morning when the streets were empty. It was extremely peaceful and I am grateful to have gotten to see it that way as it was bustling when we returned for dinner in the evening.

-Having deep chats over cocktails with a few of the group members in a random Athens alleyway on the 2nd night, and realizing I had found my people

-All of the inside jokes and laughter along the way. I found myself constantly laughing so hard I cried and can’t remember the last time I had felt so lighthearted and carefree. 

-Loving on the dozens of cats roaming the streets of Athens, Paros, and Santorini. They were everywhere and seemed to be well fed and taken care of which made it easier to enjoy the kitty time I much needed since my own passed away last year. 

“THIS TRIP WAS TRULY MADE FOR EVERYONE AND WAS THE PERFECT COMBINATION OF PLANNED ACTIVITIES AND FREE TIME”

● What advice would you give to someone thinking of booking?

Just go for it! Whether you are an introvert or extrovert, have gone on a solo group trip before or not, or are there to see the sights or relax on the beach, you will enjoy yourself! This trip was truly made for everyone and was the perfect combination of planned activities and free time.

I do recommend booking at least a couple extra days at the start/end of the trip, as the 6 full days with the group did not feel like enough coming all the way from California. I was grateful to have an extra day in Athens at the beginning to do more exploring, and an extra day in Santorini at the end to relax in solitude prior to heading back to the chaos of real life. OPA!