Man, did I ever get tired of hearing the same garbage advice every time I mentioned traveling. And trust me, I’ve traveled. A lot. But every time you mention stepping out of peak season, especially when you are chasing the sun in Europe, everyone suddenly becomes a weather expert predicting frostbite.
I needed a getaway badly. September had crushed me with work, the kind of professional grind where you start seeing the spreadsheet numbers when you close your eyes. So, come late September, I grabbed my phone and started scrolling for cheap flights. Greece. October. Everyone, and I mean everyone, online and off, yelled the same thing: “It’s too cold, you idiot! Pack proper jackets! It’s basically winter on the islands!”
Did I listen? Mostly, yeah. Why? Because I remembered that trip three years back when I tried to look cool in Venice in late October with just a thin denim jacket and nearly developed pneumonia. So, I started my Greek packing mission based on fear, not facts. Fear is a terrible packing consultant.
The Great Packing Disaster of ’23
I pulled out every piece of autumnal gear I owned. I dragged that huge, old roller bag out of the attic—the one that always gets flagged by the airline scale for being overweight. I spent an entire afternoon trying to cram three heavy jumpers, two pairs of thermal leggings (seriously, why?), and that waterproof, hooded jacket that makes me look like a yellow traffic cone into that case. I was actively ignoring the weather forecast that said 24°C (75°F) for the day we arrived in Crete. I figured, “Better safe than sorry.” That’s the classic over-planner’s downfall, right?
I even struggled to zip the suitcase shut, jumping on it like I was trying to win a wrestling match. My wife just stood there, shaking her head, asking if I was planning on scaling Mount Olympus or sitting by the beach. I told her the wind chill off the Aegean Sea was legendary. Total nonsense, I know now. That entire process of deciding what to pack was fueled by the memory of previous travel mistakes, not the current climate reality.
We landed in Heraklion, Crete, and stepped off the plane. The second that dry, warm air hit my face, I knew I had screwed up royally. I was wearing thick jeans and a heavy long-sleeved shirt for the flight because airports are always freezing, right? I was sweating before I even got to baggage claim. I practically ripped those clothes off the minute we got to the hotel room and immediately chucked them into the far corner of the closet. The feeling of pure dread when you realize you have to lug 20 pounds of unnecessary wool around for 10 days hits hard.
October Greece: The Daily Practice
The whole point of this trip, accidentally, turned into a practical experiment: just how wrong was the internet about autumn in the Mediterranean?
For the next ten days, I methodically tracked what I actually used versus what I had lugged across Europe. I kept a little notebook, scribbling down what time the temperature felt like it changed and what garment I actually put on. Here’s the day-to-day breakdown of the reality versus the fear:
- 8:00 AM to 11:00 AM (Morning Exploration): Crisp, yes, but immediate sun. I always started the day in shorts and a T-shirt. Maybe, maybe a light shawl thrown around my shoulders for the first hour of coffee on the terrace, but that came off fast, usually before 9:30 AM.
- 11:00 AM to 4:00 PM (Peak Sun): This was pure, undeniable summer. Straight-up swimming weather. We spent most afternoons baking on Preveli beach. I used my heavy sweater exactly zero times. I used my heavy-duty polarized sunglasses constantly. I used three bottles of sunscreen for ten days.
- 4:00 PM to Sunset: Still perfectly comfortable. The shadows started getting longer, and sometimes a slight breeze picked up near the coast, but nothing demanding more than a light cover-up thrown over the shoulders.
- 8:00 PM Onwards (Dinner/Drinks): Okay, this is where the gear I did bring finally came into play. The temperature definitely drops when the sun vanishes, especially if you are sitting at an outdoor taverna. But we are talking 15°C (59°F) or maybe 17°C (63°F), not freezing. The MVP here was one single, medium-weight denim jacket. Nothing more.
I carried that ridiculously heavy backpack filled with emergency cold weather gear everywhere for two full days until I gave up out of sheer exhaustion. It felt like carrying bricks. That fear-based packing added zero value and maximum back strain. I realized the only reason I brought those heavy clothes was psychological. I had been burned before by European shoulder season, and I refused to let it happen again, even though the geography and climate were completely different. Greece in October is simply not like Northern Italy in October.
Why do I bother detailing this mess? Because if you are reading this now, planning your own October escape, you are probably going through the same anxiety I did. You don’t need the extra weight, trust me. You need space in your suitcase for souvenirs—maybe some olive oil or Raki—not unnecessary wool.
The Real Essentials I Should Have Packed
After forcing myself to live through this packing mistake, I boiled the successful list down to these absolute, non-negotiable items for a sunny October trip to the Greek islands. Forget the thermals, seriously!
Dump the sweaters and grab these instead:
- Sun Protection is God: Sunscreen, the strongest stuff you can find. October sun is sneaky powerful and you burn faster when the air is cooler.
- Shorts and Tees: Mostly breezy linen or cotton shorts and plenty of simple T-shirts. Focus on light colors to reflect heat.
- One Decent Cover-Up: A light, oversized linen shirt or a breezy dress that works over a swimsuit and also for a casual dinner. Versatility saves space.
- The Nighttime MVP: One single, medium-weight jacket. Not a parka, not a thick wool coat. Just one denim or bomber jacket. This handles the evening chill near the water.
- Swimsuit, Duh: Seriously, you will swim. The water temperature holds the heat far longer than the land does. Don’t let anyone tell you otherwise.
- Footwear: Flip-flops for the beach, comfortable walking sandals or trainers for exploring the ancient sites. Forget the heavy hiking boots.
My final takeaway? October in Greece is late summer, not early fall. If you are debating between packing a massive coat or another bathing suit, throw in the suit. I’m telling you this as a guy who wasted three feet of suitcase space on a trip where I spent half my time complaining I was too hot. Learn from my heavy-luggage trauma and travel light, you’ll thank me later when you aren’t fighting the baggage carousel.