After two decades of waiting for the perfect travel companion, I finally decided to embark on my second solo trip. The desire for a real vacation, coupled with the need to break free from the confines of waiting for someone else’s schedule, led me to take the leap into solo travel once again. This time, I was determined to explore the enchanting Greek Isles.
With no idea where to start, I turned to the internet in search of “singles trips.” While cruises kept popping up, I yearned for a more immersive experience, where I could spend quality time in each destination. Seeking guidance, I reached out to a travel agent named Ellen, Avoya Travel, who helped me craft the perfect itinerary spanning Mykonos, Santorini, and Crete. Ellen’s expertise and meticulous planning made the process seamless. From arranging flights and ferries, to transportation between airports, hotels, and ports, to providing detailed vouchers and instructions, she alleviated much of the stress associated with solo travel logistics.
As the departure date approached, a whirlwind of emotions consumed me. Excitement mingled with worry, and doubts crept in about the wisdom of traveling alone. Despite my reservations, the support and enthusiasm from friends and family raised my spirits. One of my primary concerns was navigating social situations alone, particularly during evenings. Would I be confined to the solitude of my hotel room? How much money should I budget for meals and incidental expenses? These questions loomed large as I scoured websites for guidance.
Despite the initial nerves and uncertainties, my solo journey through the Greek Isles exceeded all expectations. From savoring local cuisine to marveling at breathtaking sunsets, to meeting other women solo travelers, each moment was permeated with a sense of freedom and discovery.
Mykonos: A Warm Welcome and Serendipitous Encounters
Arriving in Athens, I attempted to navigate through the airport, observing signs in Greek. I blindly followed the mass of people navigating from arrivals to connections for my plane to Mykonos. The security officer looked at me curiously when I started taking my shoes off to go through the security check. It was not needed.
Upon my arrival in Mykonos, my driver was waiting with a sign in hand with my last name. What a relief not having to hail a cab and negotiate the fare. He dropped me off, taking my luggage into the lobby of the Mykonos Princess Hotel. The staff was wonderful and each day the hotel staff and I would greet each other with “Kalimera.” Unfortunately, I had not learned the tip of getting outside in the sun and headed straight to bed, waking up around 1 pm. I meandered down to the restaurant for some lunch – a Greek salad, of course, and it was delicious. As I sat looking out at the ocean, I could not believe how blue the water appeared.
My days in Mykonos were a delightful blur of leisurely pursuits: basking on the beach, browsing through charming boutiques, and gliding serenely across the Aegean on boat rides, punctuated by refreshing dips in the sea. Despite my ability to swim, I confess to a lingering unease in deep waters; I like to be able to stand with head above water at any time. Also, I don’t like not being able to see what swimming around me might be. Silly, I know. Not to miss the opportunity of saying I’ve been in the Aegean Sea, I doggy paddled alongside the boat allowing me to grasp on to the boat intermittently.
My first evening in Mykonos, I ventured to catch the town bus to Chora to meander the quaint pedestrian-friendly streets. The area was full of life with shops, restaurants, and bars. Along my walk, I grabbed some Baklava and marveled at its affordability. I also stumbled across a jewelry store with a sign in the window “Boca Raton, FL.” I got a kick out of that and struck up a conversation with the owner. I ended my evening with a drink and watching the sun fall into the Aegean Sea.
Funny stories:
While waiting for the bus a local man on a vespa extended the offer of a ride, which I politely declined, finding the offer rather amusing.
Locating the right bus heading back to my hotel became a delightful scavenger hunt and my introduction to the relaxed pace of ‘Greek time’.
The next evening, I booked a sunset cruise. I met a group of Americans who welcomed me to join them as we sailed out to watch the sunset. After the sail, I stopped at a beach-front restaurant to have dinner. I started a conversation with the couple sitting next to me by asking where they were from and how long they were visiting. It was a nice casual and non-intrusive conversation. Upon leaving, I met another couple from England who asked if I was American. I said yes, wondering what their reaction would be. They asked if they could buy me a drink and talk. We sat at the bar and had a lovely conversation. They were very eager to hear all about America.
Santorini: Dreamy Sunsets and New Friendships
After indulging in three full days of Mykonos’s charms, it was time to bid Αντίο and embark on the ferry journey to Santorini.
The ferry ride to Santorini was magical. As we approached the island, I could start to see the famous sugar-cubed cave homes climbing up the cliffsides. Tears welled up in my eyes as the beauty of the island came closer and closer. After departing the ferry, I again found my driver in an even bigger sea of people and taxis. Grateful not to have to negotiate with a taxi service, my driver whisked me away on a journey up winding cliffside roads that made me both dizzy and exhilarated. We arrived at my hotel, Ira Santorini in Firostefani, which sits on the edge of the cliff. The porter carried my luggage and guided me down the steps to the hotel lobby where my gracious, fatherly hotel manager warmly welcomed me and gave me a great overview of the property, including restaurant recommendations and things to do in Fira, the main town. He also gave me some safety tips, including to avoid mixed cocktails and keeping an eye on my drink.
My room, with its regal ambiance, boasted a private terrace for two, offering a front-row seat to the mesmerizing spectacle of the sun sinking into the Caldera. I was so excited I called my sister to tell her I was safe and share my excitement. After sunset, adorned for the evening, I meandered down the ancient cobblestone path toward Fira, stumbling upon a hole-in-the-wall souvlaki joint, where I placed my order at the kitchen window. Another day, I discovered a quaint coffee shop and developed a fondness for Greek frappes, Nescafe instant coffee, and water shaken to create a foam, then add milk and sugar. I’ve tried recreating at home, but it’s just not the same.
On day two, I boarded yet another city bus bound for the picturesque town of Oia and struck up a conversation with a couple sitting behind me. Can you believe they were from my hometown in Pennsylvania! Oia unfolded before me like everything I had seen in the movie “Sisterhood of the Traveling Pants,” with its white cave dwellings, azure-domed churches, and labyrinthine stairways. Oia was bustling with people walking, shopping, dining, and photographing the awe-inspiring views. That evening, I embarked on a Santorini Volcanic Islands Cruise, making a stop at the volcano and hot springs before sailing toward Oia to witness the sunset. As I walked along the dock waiting to board the cruise, I heard a voice call out, “I know you.” I turned and looked quizzically. She said, ‘we took each other’s picture in Oia.’ As we chatted, I learned she was from Singapore and solo traveling the Greek Isles as well. We continued to share stories along the cruise and forged a bond with another solo traveler; a Greek woman seeking respite from the bustle of Athens. She would become a cherished friend, my soul sister. Twelve years later, we still talk and have traveled together.
Our next stop on that cruise was Agios Nicholaos Beach, home to the hot springs. Remember, swimming is not really my thing, and you had to swim 30 meters from the boat to the springs. My two newfound friends did not hesitate and jumped into the sea. As I watched them swim off to the hot spring, my mind was echoing, ‘don’t miss out on this opportunity.’ Despite my apprehension about swimming, I seized the opportunity and plunged into the waters, joining my newfound friends basking in the warm water. I don’t remember a lot about sitting in the water, just that it wasn’t “hot”; just warm. After a brief respite, we hurried back to the boat, and I felt a swell of pride at stepping beyond my comfort zone. As we sailed toward our post to watch the sunset, I remember thinking how blue the water was; indescribable. Later that night, my Greek soul sister and I dined at a quaint pizzeria. Yes, pizza instead of Greek food. I recall marveling at her ability to navigate cobblestone streets in heels.
On my final day in Santorini, before boarding the ferry to Crete, I rented a 4-wheeler and set off to explore the island, determined to find the beach with black sand. Despite my lack of a map, I followed the main road, watching for the road signs and resisting the urge to veer off course. I made it to the beach, located about 24 minutes southeast of Fira, capturing photos along the way before returning the 4-wheeler, sun-kissed and faintly smelling of gasoline. I collected my luggage and bid farewell to Santorini with a heavy heart, reluctant to leave its enchanting shores behind.
Crete: Unexpected Solitude and Venetian Charm
My remaining days were spent at the Blue Marine Hotel and Spa on the eastern coast of Crete. Though my ferry from Santorini had arrived two hours late, I found solace in the delectable charcuterie board awaiting me in my room. I took the porter’s advice to draw the drapes before going to bed for a restful night’s sleep. Good thing I did because the morning sun flooded my room when I opened them up the next day to take in the breathtaking vista of the resort grounds and sea, which hastened me to the poolside to soak in the morning sunshine.
I didn’t research Crete thoroughly enough before booking my trip. Initially, I was torn between Rhodes and Crete, but for some reason, I settled on Crete. The resort I stayed at was beautiful and catered mostly to European families looking for an all-inclusive getaway. I seemed to be the only single person around. Most of my days were spent relaxing on the beach or lounging by the pool.
Though I enjoyed the solitude, I regretted not exploring Crete’s offerings more fully. I would have preferred staying in Rethymno Old Town. Its charming narrow cobblestone streets are perfect for leisurely strolls, something I adore.
Despite my resort-centric stay, I did manage to explore a bit. I took a city bus to Chania’s Venetian Harbour, which instantly brought back memories of Venice, Italy, with its colorful buildings lining the waterfront. As my beautiful Greek friend is originally from Crete, my plan is to return one day and experience the island through her lens.
My last evening in Crete, since I had to be up at 3am to get to the airport, was spent at their Wellness Center experiencing an unforgettable spa treatment. I felt like a Greek Goddess.
Reflections: Embracing the Journey
Solo travel has taught me valuable lessons about independence, spontaneity, and the beauty of human connection. It’s not always easy to venture out alone, but the rewards are immeasurable. By stepping out of my comfort zone and embracing the unknown, I’ve discovered new landscapes and forged lasting friendships that transcend borders.
If you find yourself yearning for adventure, don’t wait for the perfect companion. Take the plunge and embark on a solo journey. The world is full of welcoming faces, enchanting places, and unforgettable experiences waiting to be discovered. Trust in yourself and the kindness of strangers, and you’ll find that solo travel can be one of the most liberating and rewarding experiences of your life.
So, here’s to the dreamers, the adventurers, and the wanderers. May your solo journeys be filled with wonder, joy, and endless possibilities. As for me, the Greek Isles will always hold a special place in my heart, a testament to the power of solo travel and the magic of discovering the world on your own terms.