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The Olive Suitcase

ABOUT ME

Sirokos Taverna heart with family at Episkopi Beach
Santorini Jet Ski White Beach
Get to know me!

The Face Behind The Blog

Welcome to The Olive Suitcase! I’m Rachel, and I’ve been going back to Greece every single year for five years now.

Not because I ran out of other places to visit (17+ countries and counting), but because Greece is the one that keeps pulling me back.

I’m the one behind all the itineraries, photos, and slightly obsessive ferry research on this site. I help busy travelers plan Greece trips that actually flow, no wasted days, no backtracking across three islands that looked close on a map but absolutely are not.

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My Story

Blogging & Traveling Abroad

How It All Started…

I’ve traveled to over 17 countries. But Greece?

Greece is the one that stayed with me.

It wasn’t just the caldera views or the water that actually is that blue.

It was a taxi driver in Athens swapping life stories with me like we’d known each other for years.

It was a Yia Yia in our Crete neighborhood waving us down every morning until we became part of her daily routine.

It was sitting at a tiny taverna where the owner brought us dishes we didn’t order and said, “Trust me.”

The Greeks have a way of welcoming you not as a tourist, but as someone who belongs.

After five years of returning, Greece stopped being a vacation destination and started feeling like a second home.

And at some point I realized: this is what I want other people to experience.

Not a checklist trip.

The kind of trip where you sit down at dinner and think, “Now this is living.”

Rachel red dress coastal Greece
Rachel

Where the Planning Bug Started

The planning thing started long before Greece. Almost 20 years ago, I organized a trip to Germany for my mom.

She’d always dreamed of going but never would have pulled the trigger on her own. I mapped out every detail. She came home glowing and said it was one of the best experiences of her life.

That feeling of handing someone a trip they didn’t have to stress about? I’ve been chasing it ever since.

Why The Olive Suitcase

The name is literal.

My senior year of high school, my parents gave me an olive green suitcase as part of my graduation gift.

That suitcase went everywhere with me, 17+ countries over 20 years.

It was scuffed, overstuffed, and held together by stubbornness and a lot of good memories.

I eventually retired it for a newer carry-on, but I couldn’t let go of the color.

Olive green is still my thing.

The new suitcase? Also olive.

So when I needed a name for this site, it was never really a question.

The Olive Suitcase is where the travel started.

Greece is where it found its home.

Friends and family kept coming to me before their Greece trips.

“Where should we stay?” “Is Santorini worth the hype?” “How do ferries even work?”

They wanted to go, but the planning felt like a part-time job on top of an already full life.

I get it.

You’ve got maybe two weeks of vacation and a budget you’ve been saving toward for months.

You don’t want to waste a single day on a bad call.

But you also don’t have 40 hours to spend cross-referencing blog posts written by people who visited once three years ago.

So I built this. Real guides from someone who keeps going back.

Itineraries built from experience, not recycled TripAdvisor lists.

The kind of planning help I’d want if I were doing this for the first time.

What I Believe

Travel isn’t about cramming in every must-see so you can say you did it.

It’s about slowing down long enough to actually feel where you are.

Greece taught me that. It softened my pace. It made me fall in love with long dinners, with wandering without a plan, with conversations that go nowhere and everywhere at the same time.

I want you to feel that too.

If You’re Here, You’re Ready

You don’t need to have your flights booked or your islands picked. You just need someone who’s been there, keeps going back, and actually remembers what it’s like to plan a trip like this for the first time.

I’m that person.

And I promise, when you step off that plane in Greece, the only thing on your mind is going to be:

“I did it. I’m here. Now I can start living.”

Already working on your Greece itinerary?

I offer personal itinerary reviews so you can land feeling confident, not anxious.

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  • Greece Destinations
    • Home
    • Athens
    • Crete
    • Mykonos
    • Santorini
  • Explore Greece
    • Greece Travel Tips
    • Travel Resources
  • Itineraries
    • Itinerary Review
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  • About Me
  • Contact