There’s something magical about counting down to a dream vacation. Every crossed-off day on the calendar feels like unwrapping a tiny piece of anticipation. For months, I watched that Greece departure date inch closer, my excitement building with each passing week. But here’s what nobody tells you: the lead-up to an international adventure is its own wild ride, complete with to-do lists that multiply like Greek olive trees and enough pre-trip jitters to fuel the Aegean winds.

Let me take you through my preparation journey—the excitement, the stress, the chaos, and all the lessons I learned along the way.

When Reality Meets Wanderlust: The Planning Phase Begins
About three months out, I pulled out my planner and started organizing what would become my travel bible. I’m talking color-coded lists, timeline checkpoints, and sticky notes everywhere. Was it excessive? Maybe. Was it necessary when coordinating four adults (myself, my husband, my son, and my mom)? Absolutely.

My timeline looked something like this:
Three months before: This is when I tackled the big documentation items. I checked everyone’s passports to ensure they weren’t within six months of expiring—a requirement many countries have that can derail your trip if you overlook it. I also realized I needed to get my Real ID, which meant a trip to the DMV. Pro tip: schedule your DMV appointment as early as possible. Mine took three weeks just to get an appointment slot.

Two months before: Time to research Greek customs and travel requirements. I dove deep into what we could and couldn’t bring into the country, voltage converters for electronics, and cultural etiquette. I also started my wishlist of places and experiences: Santorini sunsets, ancient ruins in Athens, fresh seafood by the Mediterranean, wandering through whitewashed villages. Each addition to the list made my heart race a little faster.

Six weeks before: The shopping phase began. I needed a durable suitcase that could handle cobblestone streets and island hopping, TSA-approved carry-on bags, and all those little travel essentials you don’t think about until you need them—packing cubes, a universal adapter, portable chargers, comfortable walking shoes that didn’t scream “tourist.”

The Coordination Challenge: Herding Cats Across Time Zones
Here’s something they don’t prepare you for: being the designated trip organizer for multiple adults is like being a project manager without the authority. I found myself constantly following up with my family members about their passport information for the travel company, checking in about their packing progress, and sending reminder texts that probably drove them a little crazy. “Did you send your passport details yet?”“Have you checked the weather forecast?”“Remember, we need to be at the airport early!”
Between these coordination efforts and juggling my regular work and personal responsibilities, there were moments I wondered if the stress was worth it. Spoiler alert: it absolutely was, but those weeks felt like balancing on a tightrope while someone kept adding more items to carry.

Confronting My Fears: The Flight Anxiety
I need to be honest about something that weighed heavily on my mind: I’m terrified of heights, and flying sends my anxiety into overdrive. On a previous trip back from New York, I had a full-blown anxiety attack on the plane. The feeling of losing control at 35,000 feet, unable to escape, unable to calm down—it haunted me as this trip approached. I didn’t want my fear to steal even one moment of this adventure I’d been dreaming about. So I made an appointment with my doctor and had an open conversation about my anxiety. She prescribed anti-anxiety medication for the flight, and just knowing I had that safety net gave me some peace of mind.

If you struggle with flight anxiety, please don’t let pride or embarrassment stop you from getting help. Your mental health matters, and taking care of it is part of taking care of yourself. There’s no shame in using the tools available to ensure you can enjoy your journey.

The Night Before: Beautiful Chaos
The night before departure, my bedroom looked like a suitcase bomb had detonated. Clothes everywhere. Toiletries lined up on my dresser. Packing lists scattered across my bed. My husband picked up my mom from the airport since she’d be flying out with us from SFO the next morning, and I used every minute they were gone to triple-check everything. Did I pack enough outfits for the optional excursions we might book? Check.Sunscreen, hat, sunglasses? Check.Copies of important documents? Check.That one dress I absolutely wanted for photos in Santorini? Check, check, check. Sleep? That didn’t make the checklist. My mind was racing through scenarios, mentally walking through each day of the trip, replaying my packing list like a meditation mantra. Overthinking is my superpower, and that night, it was working overtime.

Departure Day: When Plans Meet Reality
My alarm went off far too early, but adrenaline had already kicked in. One final sweep: suitcase check, documentation check, chargers check, anxiety medication tucked safely in my carry-on. We headed out the door, my stomach doing excited flips.
We arrived at SFO a full 3.5 hours before our flight—better safe than sorry, right? Turns out, everyone else had the same idea. The airport was absolutely packed. The line for Turkish Airlines stretched so far I couldn’t see the end, and it crawled forward at a pace that would make a snail impatient.

When we finally reached the counter, we discovered they were using e-tickets sent via text message link directly to your phone. Modern convenience, right? Except my mom couldn’t access hers. Cue the mini-crisis. She had to get back in that endless line to get a physical ticket printed. My carefully planned timeline suddenly felt very fragile. But here’s the thing about travel: flexibility is your best friend. We rolled with it, and eventually, everything smoothed out.

The Waiting Game: Final Countdown
With our boarding passes secured (and my mom’s printed ticket safely in hand), we had quite a wait before departure. We grabbed food, browsed the airport shops where everything costs three times more than it should, and I even managed to respond to some work emails on my phone because apparently, I can’t fully disconnect until wheels are up.

As we sat at our gate, watching planes take off and land, the nerves and excitement swirled together into this electric anticipation. I was nervous about the flight, yes, but I was also ready. Ready for the adventure. Ready for the memories we were about to create. Ready to finally see the Greece I’d been dreaming about for so long.

Practical Tips for Your Own Pre-Trip Journey
Start early with documentation: Check passports, get your Real ID, and handle any visa requirements at least three months out. Government processes take time, and you don’t want surprises.

Create a master packing list: Write it down and check it multiple times. Include categories: clothing, toiletries, electronics, documents, medications, and “don’t forget” items (chargers, adapters, comfortable shoes).

Research your destination thoroughly: Understand customs regulations, cultural norms, and practical logistics. It’ll save you stress and help you pack appropriately.

Invest in quality travel gear: A good suitcase and carry-on are worth their weight in gold (or drachmas). They’ll serve you for years to come.

Address your anxieties head-on: Whether it’s flight anxiety, health concerns, or fear of the unknown, talk to professionals and prepare solutions in advance.

Build in buffer time: Arrive at the airport earlier than you think necessary. Lines are unpredictable, and peace of mind is priceless.

Be the organized one, but release some control: If you’re coordinating with others, do your best but remember you can only control your own preparation. Set deadlines, send reminders, then let it go.

Embrace the chaos: The preparation process is messy and stressful, but it’s also part of the journey. Those late nights packing and early mornings at the airport become part of your travel story.

The Journey Begins
As we counted down the final seconds until boarding, exhausted from the preparation marathon but buzzing with excitement, I realized something important: all the stress, all the planning, all the sleepless nights were just the price of admission for something extraordinary.
The dream vacation I’d been imagining was about to become reality, one flight, one island, one sunset at a time. And honestly? Even with the chaos, even with the anxiety, even with my bedroom looking like a warzone and my to-do lists never quite complete—it was all worth it.
Greece was waiting, and we were finally on our way.

Stay tuned for the next post where I’ll share what actually happened when we landed in this beautiful Mediterranean paradise. Spoiler: reality exceeded every expectation.