Italy Travel Agent Specialist | Expert Planning

View My Main Profile
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 >
About
Reviews
Certificates & Awards
My Places
Travel Stories & Media
Client Testimonials

Areas of expertise

Destinations:

Italy, Rome, Venice, Amalfi, Sicily

Interests:

Culinary & Foodie, Arts & Culture, Couples & Romance, Family Vacations, Bespoke Travel

About Me

Venice, Italy
Venice, Italy

Italy rewards good planning more than almost anywhere else. Traveling to Italy without a clear plan tends to mean queues at sites bookable in advance, stays in the wrong neighborhoods, and a pace that leaves you drained rather than recharged. I make sure that does not happen.

WHO IS PLANNING A TRIP TO ITALY AND WHAT THEY ARE REALLY AFTER

Whatever brings you to Italy, the trip should reflect that, not a template that fits everyone and lands for no one.

  • First-Time Explorers: Rome, Florence, and Venice are on the list and you want all three to land right. When planning a trip to Italy for the first time, I lock in timed entry to the Borghese Gallery, match you with a Rome specialist, and build in a half-day in Siena or Pisa for the Italy the main cities cannot show you.

  • Families: Italy works well for families when the setup is right. I hand-select farmhouses in Tuscany with verified pools, build in gladiator school at the Colosseum and boat days off Sardinia, and pace a family trip to Italy so the adults enjoy it as much as the children do.

  • Culinary and Wine Enthusiasts: The food and wine are the whole point and I build the itinerary around the reservation calendar first. A Bolognese osteria in the Quadrilatero booked months out, a morning at the Alba truffle market in October, and a Barolo producer in the Langhe outside the standard tasting circuit.

  • Art and History Enthusiasts: A general museum visit is not what you are after. I match you with guides holding specialist credentials. A Florentine Renaissance painting expert at the Uffizi asks different questions than a guide who knows the trulli villages and cave dwellings of Puglia, and I pair you with the right one. For clients with Italian roots, I connect with researchers in Calabria and Sicily who know the archives that were never digitized.

  • Romantic and Milestone Travelers: This trip means something and the details matter more than usual. An evening at the Milan opera house during La Scala fall season, a suite on the Amalfi Coast in late May, or days on Lake Como before the summer crowds arrive. I focus on the choices that make the difference.

  • Alpine and Active Travelers: The Dolomites are world-class and most American travelers have barely discovered them. In winter I plan the Sellaronda circuit knowing the right direction and the right stops. In summer I coordinate hikes along the Alta Via 1 with rifugio bookings secured well ahead. The South Tyrol properties I work with pair direct trail access with serious spa facilities.

WHY ITALY TRAVEL EXPERTS MAKE A REAL DIFFERENCE

The quality of an Italy trip often comes down to details most people do not think about until they are already there. My contacts across Italy mean I can move quickly on hard-to-get reservations, match you with specialist guides, and find properties that never appear on standard platforms. As an independent advisor, every detail is handled directly and with full discretion. Among Italy travel experts, the difference comes down to relationships rather than research, and that is what I bring to the table.

FREQUENTLY ASKED QUESTIONS

Q: How far in advance should I start planning an Italy trip?
A:
Six to nine months is a comfortable window. The Borghese Gallery books out fastest, with capped two-hour entry slots. The Vatican Museums, Uffizi, and Colosseum underground all need advance reservations. Once your dates are confirmed, I handle every booking.

Q: Do I need a rental car, and how do the driving restrictions work?
A:
In Rome, Florence, and Venice, a car is more trouble than it is worth. Each historic center has restricted traffic zones called ZTLs, and entering one without a permit triggers an automatic fine. For Tuscany, Piedmont, or the Dolomites, a car is the right call.

Q: Is there a destination that works well as an add-on to Italy?
A:
Two come up most often. The French Riviera is an easy flight from Rome or Milan with a different feel but the same Mediterranean ease. Croatia's Istrian Peninsula pairs great seafood, local wine, and truffle country with coastline at a lower price point.

READY TO SEE ITALY WITHOUT THE GUESSWORK?

Send me a note with your travel window and what the trip means to you, and I will put together a plan worth your time.

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.
Search reviews:

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.
ITALIA's Travel to Italy Specialist certification

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

A colosseum selfie in Rome, Italy

Autumn in Umbria and Rome

I arrived in Rome just after noon and headed straight to Palazzo Manfredi, a Relais & Châteaux property across from the Colosseum. From the rooftop, you can see the entire amphitheater illuminated at night...an unforgettable backdrop to your first glass of wine. I had one night in the city before heading north to Umbria, and this hotel offered t...
Read more

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
BESbswy