Dreaming of Greece: My Big Fat Greek Family Vacay
It’s been two months since I got back from my Big Fat Greek Family Vacation, but it still feels like yesterday. Maybe that’s because there was so much to unpack (pun very much intended) — from ferry tickets to family drama — that I didn’t know where to start.
Planning a trip for this crew was no small feat: two slightly cynical Gen-X couples, four Gen Z’ers, one “Mayor Grandpa,” and Flat Michael (the stand-in for my son) who had to change his plans last minute. (Don’t worry, he didn’t suffer from any FOMO; we promised him a do-over trip in cooler weather.)
Meet the CEO/CFO
I somehow got nominated to run the family C-suite: CEO (Chief Excursion Officer) by day, CFO (Chief Freddo Officer) by… every hour that required caffeine. Normally, I’m more of a “plan the big stuff, leave the rest to chance” kind of traveler. But since no one else raised their hand — and I’ve been to Greece quite a few times — the nomination stuck.
The challenge? Squeeze ancestral roots (Sparta and Crete), family introductions, and “Instagrammable” experiences into two weeks. Did I back down? Of course not. Armed with itineraries, ferry tickets, and Freddos, I kept this traveling circus on the road.
Pre-Game Fuel: Athens & Tinos
Before the full family circus arrived, my husband and I gifted ourselves an extra week. Athens was for hugs, coffee, and family catch-ups. A special time with my rambunctious four-year-old godson and my godmother, who delayed her own trip just to see me.
Then came Tinos: milestone-anniversary, romance and a pilgrimage to the Church of Panagia Evangelistria. We left lighter, caffeinated, and (mostly) ready for the joyful chaos ahead.
The Itinerary in a Nutshell
The route: New York → Athens → Gítheio, Sparta (3 nights) → Crete: Agios Nikolaos (3), Rethymno (3), Heraklion (2) → Athens (2) → Back to New York.
Would I recommend this exact route? Not exactly. The travel days were a bit long, and our mini-bus gave us more togetherness than any of us ordered off the menu. Usually, I’d plan in a loop or group areas to cut down on back-and-forth. But since our family roots are split between Sparta (my in-laws) and Crete, the itinerary called for a little retracing. In the end, it was worth it — because great memories are made when you cram nine relatives and one cardboard cutout into the same vehicle.
My brother-in-law nicknamed our driver “Turbo” (because he wasn’t). Nia made sure Flat Mike was buckled in and “caffeinated.” We ribbed each other between naps, stopped to see the breathtaking Corinth Canal, and yes—I walked across the shaky bridge. Did I look down? Absolutely not. Did I stop mid-span for photos and video? Absolutely yes. Official family photographer never rests.
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When Double Dates Become Group Meals
We expected a few peaceful double dates while the “kids” YOLO’d around Greece. Plot twist: they did their thing by day, but reappeared like clockwork at our dinners.
They stuck to us like sand at sunset. Apparently my itinerary was too good—fully Gen Z–approved. And since we picked the spots with linen napkins and sea views, they ordered like it was their last supper. “For the table,” naturally.
At some point, I couldn’t decide between boundaries vs. saganaki, so I did the Greek thing: smiled, waved the card, and ordered another round of Raki… or a Freddo. Who’s counting?
Family Highlights Reel
Some moments just can’t be described — they have to be seen.
Catch our favorite snapshots from Athens, Sparta, and Crete (yes, Flat Mike included).
What’s Coming Next
🎬 Coming Soon on Dreaming of Greece:
Ever Travel With the Mayor? (aka Grandpa™ on tour)
The Adventures of Flat Mike (spoiler: he was a better tour guide sign than any umbrella)
Kids vs. Menus: The Last Supper Energy
Plus: Sign up for the newsletter to get subscriber-only guide with all the food, hotels, and pro tips from our route.
Stay tuned—because if there’s one thing I learned, it’s that the stories are even bigger than the itinerary.