Photo: Megan Brown
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Visiting Greece had been at the top of my bucket list for years. I dreamed of blue domed buildings in Santorini, wandering ancient ruins in Athens, and dipping my toes into the Aegean Sea. When I finally booked my trip — Athens, Santorini, Paros, and Naxos — I was beyond excited. My Pinterest board was full. My hopes were high. And while I did have an unforgettable trip, I also made a few rookie errors that definitely impacted the experience.
If you’re planning your first Greek getaway, hopefully these five beginner mistakes can help you avoid the same travel headaches I faced.
1. Going in the off-season
My trip was at the end of February. It sounded perfect in theory: cheaper flights, fewer crowds, milder heat, but I didn’t realize just how off the off-season would be. On the islands, many restaurants, shops, and even ferry routes were shut down or extremely limited. The beaches were empty (and chilly), and some areas felt eerily quiet.
If you’re traveling outside of peak months, research how the seasonal shifts affect Greek destinations. You can still have an amazing trip in the off-season, but you’ll need to adjust expectations and plan for limited services.
Image source:Megan Brown
2. Bringing a wheeled suitcase
The cobblestone streets of Athens and the countless stairs in Santorini were no match for my rolling suitcase. I spent way too much time dragging, lifting, and awkwardly navigating it through narrow alleys and steep steps. It was loud, inconvenient, and honestly made me wish I’d just packed less.
Next time, I’m going hands-free with a backpack or lightweight duffel. You’ll thank yourself when you’re trying to board a ferry or navigate steep alleys in Santorini.
3. Not packing cash
I was so used to tapping my card for everything that I assumed Greece would be the same, but many places in Greece, especially on the islands, are cash-preferred or cash-only. I ended up scrambling to find ATMs and racking up some annoying foreign transaction fees, which isn’t fun when you’re hungry and jet-lagged.
Now I know: always carry a stash of euros. It’s especially important for tipping, small purchases, and island travel.
Image source:Megan Brown
4. Packing only warm weather clothes
I thought, “It’s Greece! It’ll be warm.” Spoiler: it wasn’t. When I visited, temperatures were cool and often windy, especially on the islands, and I packed nothing but sundresses, sandals, and linen pants. I ended up wearing the same sweater almost every day and was freezing most nights.
Layers are key! Even in warmer months, bringing a light jacket and jeans can save you.
5. Only planning one day for Athens
I treated Athens like a layover on my way to the islands, giving myself just one rushed day. Big mistake. The city is bursting with history, culture, and cool neighborhoods worth exploring. I barely scratched the surface and I still regret not giving it more time.
From the Acropolis to the hidden cafes in Plaka to picturesque Anafiotika, Athens deserves at least two full days. Trust me, you’ll want that extra time.
Image source:Megan Brown
Why I’d travel with Contiki next time
Planning a trip to Greece on your own can be a lot. From ferry schedules to hotel bookings to figuring out which beach is actually worth the hype. It’s easy to get overwhelmed, especially if you’re a first-time or solo traveller.
That’s why I’d go with Contiki for my next adventure. They take care of the logistics, introduce you to fellow travellers, and give you a curated experience without stripping away the freedom to explore. Plus, each trip comes with a Trip Manager who’s with you every step of the way. They’re there to offer helpful tips, sort out any unexpected issues, and keep the energy high. Whether you’re flying for the first time or just want a trip that’s fun and stress-free, Contiki makes it easier to actually enjoy your vacation.
My next Greek adventure? I’ll be letting the experts handle the planning so I can just soak up the sunshine, olives, and ouzo.
