Greece Lefkada (Ionian) Travel Advisor Specialist

View My Main Profile
Emily Stewart, Travel Agent in Chicago, IL

Emily Stewart

Chicago, IL Travel Agent
Super Agent

Emily Stewart

Chicago, IL · 6 Years of Experience

Emily Stewart, an independent agent with Travel Leaders Davis, CA
5.0
(21)
100% Recommended
Thanks Emily for a well planned weekend in Chicago. We are all married with kids and wanted to plan a trip away. She recommended the best... Read More >
About
Reviews
My Places
Travel Stories & Media

Areas of expertise

Destinations:

Greece, Lefkada, Cephalonia, Corfu, Zakinthos

Interests:

Beach Vacations, Family Vacations, Nature, Sailing & Boating, Wellness

About Me

Porto Katsiki Legendarily Beautiful Beach
Porto Katsiki Legendarily Beautiful Beach

Why I’m the Perfect Person to Plan Your Trip to Greece

A Love Letter from Someone Who Lived It

When people dream of Greece, they picture whitewashed villages, golden sunsets, and turquoise seas — and while all of that is real, it barely scratches the surface. Greece is a one of a kind place that I was fortunate enough to live in for a few months! From sailing through the Ionian to sipping ouzo with locals, I immersed myself in every part of Greek life. I learned its tendencies, its language, its flavors — and I want to help you experience that side of Greece, too. Not just the picture-perfect one, but the living, breathing, magic-filled one that you carry home with you.

I Lived in a Cat Sanctuary (Yes, Really)

I began my Greek journey in the most unexpected way: surrounded by cats on a hillside overlooking the sea. I lived in a cat sanctuary with dozens of furry companions, each with its own quirks and charm. My days started with morning light spilling through olive trees, coffee in hand, and a few dozen curious eyes watching me stretch. That sanctuary taught me to slow down and live in the present — a lesson that shaped the rest of my time in Greece.

I Learned to Sail in the Ionian

Learning to sail was one of the most exhilarating things I’ve ever done. The Ionian Sea is a dream — calm waters, hidden coves, and islands that rise out of the sea like secrets. I spent days out on the water, learning the ropes from seasoned skippers and exploring bays most tourists never find. Whether you're craving adventure or serenity, a sailing trip in Greece is something I can confidently plan — because I’ve lived it, sunburns, rope burns, and all.

I Learned to Speak (and Feel) the Language

I didn’t become fluent, but I learned to speak with respect and heart. I practiced “efharistó” (thank you) until I could say it like a local — not just as a word, but as a way of connecting. Greeks are warm and generous, and making even a small effort with the language opened up conversations, laughter, and friendships I’ll never forget.

I Swam in Waterfalls and Fell in Love (Maybe More Than Once)

Just outside Nydri is a waterfall I visited often — a quiet little Eden tucked into the trees. I’d go for a dip, journal in the shade, or simply sit and listen to the sound of water on rock. Greece has a way of making even the smallest moment feel like a gift.And yes, I kissed a few Greek men. There’s something about the romance of Greece — the way the stars hang low, the sea breeze wraps around you, and the people flirt like poets. It’s not always about grand love stories, but about letting yourself be open to beauty, connection, and the unexpected.

I Fell in Love With the Beaches

Let’s talk about the beaches — because they deserve their own love letter. Desimi was my quiet escape, a peaceful bay where the water was as calm as glass. I swam and floated, often with no one else around. Porto Katsiki, framed by stunning cliffs and brilliant turquoise waters, was dramatic and cinematic — a place that made me gasp every time I saw it. Nydri Beach was my daily favorite, perfect for a post-painting dip or lazy afternoon sunbathing. Vliho and Perigali offered a more local, laid-back feel, where the Ionian Sea lapped gently at the shore and time seemed to stretch. These beaches aren’t just beautiful — they’re soulful, and I know exactly when and how to enjoy them without the crowds.

I Painted, Practiced Yoga, and Ate Like a Goddess

Greece gave me the space to reconnect with myself. I deepened my kundalini yoga practice in open-air spaces, painted daily, and found inspiration in every shade of blue. I also spent time in local kitchens learning to cook pastitsio (a savory pie I dream about to this day) and classic, comforting moussaka.The meals? Unreal. Whether it was grilled octopus on the water, buttery spanakopita in a stone courtyard, or a spoonful of honey-drenched loukoumades, I ate with joy and gratitude. I sipped ouzo, clinked glasses with expats and locals, and learned how much of Greek life happens around the table.

I Worked Remotely and Built a Life

Even in the midst of paradise, life kept going — and I kept teaching English from my laptop. I juggled Wi-Fi connections, time zones, and lesson plans, and in the process, learned how to blend work with wanderlust. I can help you do the same — whether you're looking to work remotely, take a creative sabbatical, or simply find a place to pause and dream again.

 

So... I’ve done it. I didn’t just skim the surface — I dove in, heart first. I’ve lived the quiet mornings, the thrilling adventures, the odd missteps, and the unforgettable moments that make Greece more than a vacation spot — they make it a story worth telling.Whether you want to hop islands, find the best hidden beach, eat like a local, or unplug completely, I know how to design an experience that’s deeply personal and completely unforgettable.Let me help you fall in love with Greece — with an open heart.

REVIEWS

Rating: 5.0
21 reviews
100% Recommended
Your trust is our priority. Every review is submitted by verified travelers after they have booked and completed their trips. Learn more about our review guidelines.
Search reviews:

Showing 21 reviews

Chi-Town
Reviewed By Griffin T - Dallas, Texas | Traveled to Chicago | Illinois | USA
Thanks Emily for a well planned weekend in Chicago. We are all married with kids and wanted to plan a trip away. She recommended the best restaurants (Chicago's food scene is unreal) —we all left a few pounds heavier. Luckily we didn't have any flying delays. 5 stars!
Emily Stewart responded
"My pleasure! So glad you enjoyed yourself."
I would recommend this agent to my family and friends.
0 of 0 people found this review helpful. Was this review helpful to you?YES|NO
Perfect Trip to Lefkada
Reviewed By Priscilla Trent - New York | Traveled to Lefkada | Greece | Europe
Emily coordinated a trip for my family to go to Lefkada-- and it was incredible. We loved the greenery that the Ionian side of Greece offered. From the amazing food to the breathtaking landscapes, this was exactly what we needed to escape the hustle and bustle of the City. Thanks Emily!
I would recommend this agent to my family and friends.
0 of 0 people found this review helpful. Was this review helpful to you?YES|NO
Fun Times in Brooklyn
Reviewed By Tiffany R. - Alabama | Traveled to Brooklyn | New York | USA
I went to Brooklyn to visit some friends from college and reached out to Emily to help me find a hotel, flight, and recommend a few things to do. Overall the trip was great and all went smoothly! Thank you!!
I would recommend this agent to my family and friends.
0 of 0 people found this review helpful. Was this review helpful to you?YES|NO
Arts in Berlin!
Reviewed By Becky Vlaho - New York | Traveled to Berlin | Germany | Europe
I travelled solo to Berlin to get some inspiration for my art. With Emily's recommednations and bookings I wanted to stay weeks longer!! Overall, it was great and appreciate it so much.
I would recommend this agent to my family and friends.
0 of 0 people found this review helpful. Was this review helpful to you?YES|NO
Trip down to SB
Reviewed By Xavier - Bay Area | Traveled to Santa Barbara | California | USA
We live in the bay area so aren't very far away from Santa Barbara. We wanted to get away from the kids for a romantic anniversary weekend. Emily is quite the romantic herself!! She planned couples massages, an intimate dinner and a wine tour! The best part? On the wine tour I was connected with an old friend from the reserves. Small world! The only thing I would have changed was the checkout said Noon and they wanted us out by 11, but it ended up being ok.
I would recommend this agent to my family and friends.
0 of 0 people found this review helpful. Was this review helpful to you?YES|NO

My Places

When it comes to travel planning, real-world experience makes a huge difference. Check out the map below to see all the places I have personally visited or booked for my clients. I know these destinations well and can give you reliable guidance.

My Travel Stories

Water in Greece is Unparralleled

Learning to Sail in the Ionian

Learning to Sail in the Ionian Sea — With Bob, Beer, and Beautiful Chaos I never thought I’d learn to sail — not properly, at least. But then came the Ionian Sea, the salty mentorship of my friend Bob, and the wild, wonderful sailing community of Lefkas. Somewhere between wrestling lines, drinking beers at dockside tavernas, and watching ...
Read more

BESbswy