Sea Legs and Side Streets: Wandering the Greek Isles

Cruising is one of the only forms of travel where you can wake up in a new country each day without ever having to repack your suitcase. This particular voyage began and ended in Athens (Piraeus), looping through the Aegean with a detour to Istanbul—our first port of call after setting sail. What followed was a string of Greek islands, ancient ruins, and enough olive oil to moisturize a small army.

Embarkation in Piraeus, Greece

The port for Athens is in Piraeus, about 10km or 6 miles from Athens city center. Traffic can be terrible depending on your arrival time so taxis and Uber rates vary widely. You could take the metro if you're adventurous or the express X96 bus like I did. I wouldn't recommend that option if you have a lot of luggage as you'll need to walk from the bus stop to where you're staying. I thankfully chose a hotel just a half block from one of the bus stops so it was super easy and convenient - only costing 5 euro. Seeing as I arrived in the late afternoon, I opted to go directly to the port so my embarkation the next morning would be quick and easy. I found a lovely and reasonable 4 star hotel that had a rooftop cocktail bar for sunset views over the harbor.

Cruise tip: Depending whether you're flying in to your departure city early or not, opting to stay near the port where you'll be embarking is a good way to have a relaxing, stress-free morning. I would not recommend this option for all ports (for sure NOT Callao, Peru), but for Piraeus it was wonderful.

Istanbul, Turkey

We began in a city that still answers to Constantinople—especially if you’re speaking to a Greek or a history professor with tenure. Istanbul is a layered cake of empires, mosques, and weather patterns. I wandered until my feet staged a mutiny, dodging carpet salesmen and befriending cats who clearly run the place. The city is beautiful, chaotic, and deeply photogenic.

The photo above is of the Galata Bridge connecting the new part with the old part of the European side of Istanbul. Fishermen, cars, and pedestrians are on the top deck while restaurants are on the bottom deck - serving up the freshly caught fish and octopus.

Thessaloniki, Greece

Thessaloniki felt like Athens’ younger sibling who’s trying to prove something. The ruins are wedged between apartment blocks like forgotten leftovers from a toga party. The traffic is relentless, the waterfront is walkable, and Alexander the Great would probably opt for a scooter if he were around today.

Volos, Greece

Volos was a breath of misty, mountain air. I skipped the harbor and ascended Mount Pelion on a ship excursion, where the rain politely took turns with the sunshine. The view was the kind that makes you whisper “wow” even though no one’s around to hear it. No crowds, no chaos—just hillside homes clinging to the hillsides like they've been there for generations....which they have.

Mykonos, Greece

Mykonos is what happens when a postcard comes to life and decides to open a boutique. Whitewashed buildings, pink bougainvillea, and blue everything—it’s like someone spilled a Greek flag on a wedding cake. I took a mosaic-making class, which was delightfully offbeat and involved zero cruise line branding. I now own a piece of Mykonos, and it’s not a fridge magnet.

The photos above are from Mykonos. I am posing with the gorgeous bougainvillea set against the white-washed buildings and impossibly blue sky above. The other photo is of the mosaic I made during my cruise ship excursion. I got to express my creativity and come home with a unique souvenir.

Heraklion, Crete

Heraklion was… fine. It didn’t flirt with me the way Mykonos did, but it bought me lunch and introduced me to olive oil, so I can’t complain. I joined a small group excursion with a local guide who knew every goat path and family-run restaurant on the island. The olive oil factory was fascinating, and I now know more about pressing olives than I do about pressing pants.

Cruise tip: you don't have to book excursions through the cruise line. There are many tour aggregators that work with suppliers to offer cruise-friendly tours. Most have "back to ship" guarantees as well as a generous refund policy should the ship's itinerary change last minute due to weather challenges (very common in the Med due to high winds).

Rhodes, Greece

Returning to Rhodes after 35 years felt like bumping into an old friend who hasn’t aged a day—except now they have more cats. I skipped the tours and wandered solo, feeding strays and chasing nostalgia through medieval alleyways. The Colossus is long gone, and the windmills are no longer spinning, but my heart was on this fabulous island.

The photo above is within the medieval walls of old town Rhodes. The turrets, bougainvillea, and sunshine made for a perfect day to stroll around getting lost in the small alleyways.

Patmos, Greece

Patmos is where you go to contemplate life, scripture, and whether that yacht belongs to Tom Hanks. I visited the Cave of the Apocalypse, which is surprisingly cozy for a place associated with end times. No photos were allowed inside but it's still very much in use today as a church with regular services. The island is serene, exclusive, and only reachable by sea or helicopter—unless you’re a celebrity, in which case you probably arrive via divine light.

The photo above is from the town of Chora and its old windmills. The white-washed houses have flat roofs which allowed its residents to escape the pirates by jumping from one to another.

Athens, Greece

Disembarking in Athens felt like stepping into a memory. I joined a food tour that was equal parts delicious and cardiovascular. The Acropolis was as humbling as ever, and the museum reminded me that ancient Greeks were very good at carving things and very bad at modesty. This visit was a tribute to my late sister Roxane, with whom I once explored these ruins decades ago. Would I return? Absolutely. Preferably with better shoes and more time to wander.

The photos above are from Athens. The one on the top is my walking food tour guide Maria holding a platter of lamb, pork, and chicken gyros - one of six, yes six, stops for food that afternoon. The photo below that is of the Parthenon on the Acropolis. I used my camera's AI to erase the tops of the heads of all the tourists but didn't have to remove any scaffolding - my guide said our visit coincided with the least amount of scaffolding she's seen in the past 14 years!

Cruising may be the only form of travel where you can eat five meals a day and still lose weight from all the walking. It’s a strange, floating paradox—and I can’t wait to do it again.

Solo traveler tip: Cruising is an easy and relaxing way to travel; it takes the stress out of the logistics of travel overall, whether solo or not. As a solo however, you can benefit from built-in social interaction opportunities to engage with other solos and other like-minded travelers. Traveling solo via land (not on an organized tour) you are generally staying in an Airbnb or hotel, in your own room, going off and touring on your own or perhaps with a day tour that once it's over, everyone scatters back to their respective accommodations, etc. It can be very isolating.

On a cruise, especially on a small ship, there are numerous opportunities to meet others. You can still go off and do your own thing, but if you are wanting more engagement with others, you have those chances each day/evening on a cruise ship. You can dine with others. You can go to the evening shows with others. You can dance the night away with others at deck parties where no one needs a partner to have a blast. You can connect with other travelers on your shore excursions. Don't let the idea of cruising solo intimidate you. I would be more than happy to help you weigh the various options out there to find a good fit for you and your travel style, budget, and goals.