First Trip to Greece Let Me Down; What I’d Do Differently Next Time

When one of my most anticipated trips turned out to be one of my most frustrating, it was entirely my own fault.

I travel professionally for a living, but I still get caught up in excitement and unrealistic expectations when planning. Like many travelers, I’d been dreaming of Greece for years. I watched “Mamma Mia,” scrolled through Instagram, and let the images build an idea of what the trip would be like.

In the end, I left the country feeling disappointed and wishing I’d done a few things differently.

Booking a cruise instead of staying on-site didn’t give me much time to explore

This was my first mistake, and it shaped the rest of the trip. I still think cruising is a great way to see the world, just not Greece.

In my opinion, the problem comes down to numbers. The ships carry too many people, and they are all landing on a small island at once.

Santorini isn’t necessarily equipped to handle the thousands of passengers a cruise ship drops on its shores. Once you arrive, you still have to get up to the villages by tram, donkey, or a long walk.

We were the only ship in port that day, but I still had to wait several hours to reach where I wanted to explore. On a trip with limited time, that’s a hard way to start the day.

Next time, I’d actually stay in Greece.

I missed out by only planning my trip around popular islands

This was my biggest mistake. I’d seen images of Santorini’s white villages and Mykonos sunsets for years, so when I saw both islands on the cruise itinerary, I jumped at the chance to check off two places in one trip.

Greece isn’t a destination you check off a list. It’s a country meant to be savored. By choosing two of the busiest islands and spending only a day on each, I never got past the surface.

Both islands were stunning, but I felt rushed and had no time to take them all in. This showed me that my travel style leans toward quiet, undiscovered places over popular, crowded ones.

When I get to visit Greece again, I’ll skip Santorini and Mykonos and visit smaller islands that offer quieter, more authentic experiences, such as Hydra, Kimolos, or Ithaca.

Familiarizing myself with Athens before arrival would’ve improved my trip

Athens is a wonderful, historic city with plenty to see. It’s walkable, but seeing the most iconic sites still takes a plan. I didn’t have one. I thought I’d just walk around and figure it out.

That led to hours of wandering, getting lost, and losing time in the wrong parts of the city. There was plenty to experience along the way, but I could have seen far more with a plan.

Now that I know more, I’d recommend staying in Plaka — it’s within walking distance of the Acropolis, Syntagma Square, and good food and shopping.

Also, I suggest booking dinner reservations in advance so you don’t miss out on the places you actually want to try.

Pursuing specific photo opportunities wasn’t worth my time

The minute I landed in Santorini, all I wanted was a photo in front of the famous blue-domed churches.

I didn’t realize that meant walking shoulder to shoulder with thousands of other people down narrow streets where locals were just trying to run their businesses, then standing in line for over an hour for 10 seconds in front of the church.

It’s gorgeous, but not worth losing an entire day for one photo. I caught the mistake quickly and hired a local guide to take me to the other side of the island, away from the crowds.

There I found quiet beaches, black- and red-sand shorelines, and small churches with no one in line. Away from Oia, I finally found the Greece I’d pictured.

I underestimated the physical demands of exploring Greece

I’m in decent shape and travel often, but Greece wore me out.

The heat in September was more intense than I expected, and the cobblestone streets, as pretty as they look, are hard to walk on, especially when everywhere I wanted to go was uphill.

I wanted to put on cute dresses and look photo-ready wherever I went, but I ended up wearing sneakers and a ponytail just to get through the day.

If I return, I’ll pack more practical clothing, bring real sun protection, and plan around the heat instead of ignoring it.

Ultimately, I’d absolutely go back to Greece — just with a better plan next time

I had dreamt of visiting Greece for years, and as I left, I felt that the country I experienced was nothing like what I had expected.

It was maddening to realize that my disappointment would have been completely avoidable if I had planned differently.

Even though I left exhausted and frustrated, I’d still go back to Greece. I’d just travel differently — slower and more thoughtfully — so I could actually enjoy it.