Greece Travel Agent | Custom & Private Trips

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Steven Callas, Travel Agent in NorthBrook, IL

Steven Callas

NorthBrook, IL Travel Agent
Super Agent

Steven Callas

NorthBrook, IL · 3 Years of Experience

Gilded Travels LLC, an independent agent with Nexion, LLC, a Travel Leaders Network Affiliate Agency
5.0
(18)
100% Recommended
I never would have picked Mallorca as a vacation destination. My wife likes the beach, I like adventure. Gilded Travels created the perfect one-week itinerary that... Read More >
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Areas of expertise

Destinations:

Greece, Athens, Santorini, Mykonos, Crete

Interests:

Beach Vacations, Historical Sites, Honeymoons, Family Vacations, Bespoke Travel

About Me

Santorini, Greece
Santorini, Greece

Greece is not a destination I discovered. I grew up with the language, the culture, and the people. With native fluency in Greek and over 30 visits, the knowledge I bring to every Greece vacation is something no algorithm can replicate. Tell me what you want from this trip, and I will build it properly.

WHO PLANS A CUSTOM GREECE TRIP WITH ME

Greece means something different to every traveler. Here are a few of the people I work with most. If yours looks nothing like any of these, that is fine too.

  • First-Time & Aspirational Visitors: You have been picturing this trip for a while, and you want it to land exactly right. When planning a vacation to Greece for the first time, that means knowing which moments are worth building around: the Acropolis at dawn, a caldera-view room above Santorini, a quiet evening in a Mykonos backstreet before the night begins.

  • Families with Children: You want a real trip, not a resort stay. But with kids in tow, the itinerary has to work for everyone traveling with you. From two parents with young children to group trips to Greece spanning three generations, racing in the Olympic stadium at ancient Olympia, the Minoan ruins at Knossos, and sea turtle nesting beaches off Zakynthos are the experiences children talk about long after the trip ends.

  • The Discerning Explorer: You have done Mykonos and Santorini. Now you want the Greece most visitors never find. Amanzoe above the Argolic Gulf, the hot springs off Thirassia by sailboat, dinner at a Milos taverna sourcing from the island that morning, a few days on car-free Hydra. Luxury vacations in Greece at this level take an advisor who has been to these places and knows exactly who to call.

  • History & Culture Travelers: Greece is a pilgrimage for you, not a beach trip. You are tracing ancient philosophy, St. Paul’s route, or working through every UNESCO site on the map. Storytelling matters far more to you than sea views. A morning at the Parthenon before the crowds, a performance at the ancient theater of Epidaurus under open sky, followed by a night in a monastery guesthouse at Meteora. That is the kind of trip I love building.

  • Off-Season Travelers: You made a deliberate choice to skip the summer crowds, and that instinct is right. September and October mean warm water on the Athens Riviera and evenings that feel genuinely local. The harvest season, olive pressings in Crete and grape festivals on Paros, is the Greece that peak-season visitors rarely experience.

WHAT IT ACTUALLY MEANS TO WORK WITH A GREECE TRAVEL AGENT

With native fluency in Greek and over 30 visits, the relationships I have built across Greece benefit every client I work with. Each contact covers a specific region, so the advice is grounded rather than generic. As a specialist in Greece luxury travel, I know that the right Santorini room fills months before it appears online, and that a Plaka restaurant worth booking does not take walk-ins. The best travel agents for Greece have that kind of access. For clients with sensitive itineraries, that side of things is handled quietly.

FREQUENTLY ASKED QUESTIONS

Q: When is the best time to visit Greece?
A:
Mid-May through early June is the sweet spot for the islands: great weather, everything open, none of the August crowds. September and October suit slower trips and site visits. For Meteora, Delphi, and the mainland, spring and early autumn are ideal.

Q: How does island hopping work?
A:
The ferry network is reliable, with Blue Star Ferries and Seajets connecting most islands daily. For longer routes, a domestic flight saves more time than it costs. I confirm every connection and schedule in advance, so your travel days run smoothly.

Q: Can Greece connect into a broader Mediterranean trip?
A:
For the right timeline, yes. Athens to Istanbul is ninety minutes by air, and the Peloponnese pairs well with southern Italy for anyone tracing ancient history across two coastlines.

LET'S START PLANNING YOUR GREECE VACATION

If you are ready to close the tabs and let someone who actually knows Greece take it from here, reach out and we'll start with a conversation about what you want from your trip.

Additional Languages
Greek

REVIEWS

Rating: 5.0
18 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.
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Showing 18 reviews

A perfect Mallorca experience
Reviewed By Makis S. - Deerfield, IL | Traveled to Balearic Islands ~ Spain ~ Europe
I never would have picked Mallorca as a vacation destination. My wife likes the beach, I like adventure. Gilded Travels created the perfect one-week itinerary that had us exploring the beautiful beaches, hiking through rustic mountain villages, and dining at incredible restaurants on the island. No day felt too full or too empty. It was the perfect balance. Neither of us felt like we needed a "vacation from our vacation." I definitely recommend Steven and Gilded Travels and will be using them again!
I would recommend this agent to my family and friends.
6 of 7 people found this review helpful. Was this review helpful to you?YES|NO
10/10 recommend- WORTH IT!
Reviewed By Tina K - Chicago, IL | Traveled to Patagonia ~ Argentina ~ South America
Steven was amazing to work with. I’m an anxious traveler and he made the process so easy! I’ve always wanted to go to Patagonia but didn’t even know where to start. Steven took control and created an itinerary for me that I could’ve never done myself. We worked together to tweak it a bit and next thing you know I’m climbing a glacier in Argentina! 10/10 recommend his services- WORTH IT!
I would recommend this agent to my family and friends.
5 of 5 people found this review helpful. Was this review helpful to you?YES|NO
Dream Trip
Reviewed By LBACE - Mishawaka. IN | Traveled to Greece ~ Europe
My wife and I worked with Steven for a trip of a lifetime in Greece. Steven went out of his way to provide service in recommending destinations, things to do and activities at each island we visited. We enjoyed incredible accommodations while exploring Greek culture, food and beverage. This was a memorable journey, which wouldn't have been so easy without his assistance. we highly recommend Steven for help in planning your getaways!
I would recommend this agent to my family and friends.
2 of 2 people found this review helpful. Was this review helpful to you?YES|NO
Trip of a lifetime!
Reviewed By Nancy P. - Arlington Heights, IL | Traveled to Europe
My husband and I planned an ambitious European trip and Steven made it happen. He was able to take our wishes and plan an itinerary which we thoroughly enjoyed. He worked with us as we fine tuned our plans, gave us options to choose from, and answered all of our questions. We were grateful that prior to our trip he checked in to be sure we had taken care of the items we needed to handle. During our trip we experienced a train delay which caused us to miss a connecting train and Steven was able to give us guidance so we could reach our destination. It was a pleasure to work with Steven, he showed real interest in our plans, and checked in once we returned. Thanks Steven!
Steven Callas responded
"It was such a pleasure to help craft this trip for you! Thank you for your kind words. I look forward to planning another trip for you in the future!"
I would recommend this agent to my family and friends.
2 of 2 people found this review helpful. Was this review helpful to you?YES|NO
Gratitude for an excellent experience
Reviewed By Russ H. - Orlando, FL | Traveled to Jordan | Middle East
The balance was perfect; a fantastic mix of planned activities and personal time to explore. The meetings to pre-plan the trip were concise, helpful and relevant. Lots of great moments. Petra and Bethany by the Jordan were both highlights. It exceeded my expectations.
I would recommend this agent to my family and friends.
1 of 1 people found this review helpful. Was this review helpful to you?YES|NO

Certifications & Awards

Certified Leisure Travel Specialist: During this certification program Travel Agents study several key components including: Sales and Service, Cruise Sales, Destination and Lifestyle Knowledge,  Programs and Preferred Supplier Knowledge. This is a two year study program.
TBO Academy's Greece Certified Specialist

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

Enjoying the caldera in Santorini, Greece

Sunset Hikes and Wine in Santorini

I arrived in Athens in the late afternoon, greeted by a driver holding a sign with my name just outside customs. The pickup was arranged by my hotel, The Foundry Suites in Psyrri. The building used to be a print shop and has since been converted into a boutique property with twelve suites, original stone walls, and a rooftop garden that looks ou...
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Client Testimonials

Steven is your man for Japan!!
Steven was very professional with a great attention to detail. He carefully listened to what we wanted from our first trip to Japan, and he delivered! There were 3 of us traveling and he was able to plan an itinerary that met all our expectations.
Mario H. - Chicago, IL
Dream trip to Greece
My wife and I worked with Steven for a trip of a lifetime in Greece. Steven went out of his way to provide service in recommending destinations, things to do and activities at each island we visited. We enjoyed incredible accommodations while exploring Greek culture, food and beverage. This was a memorable journey, which wouldn't have been so easy without his assistance. We highly recommend Steven for help in planning your getaways!
Larry B. - Mishawaka, IN
Patagonia anniversary success
Steve was great to work with. We planned our trip in late January for November, and he guided us through it all and stayed on top of it following up with us in the fall and even checked in on the trip and after. It was great to have an expert who has traveled there really give us his recommendations. He nailed the whole trip out of the park and was one of the best life changing vacations we have taken. It was extra special because we celebrated our 20th anniversary.
Melissa H. - Riverside, IL
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