Kylie Tobasco
Based in Chicago, Illinois
Kylie Tobasco
Ask me about
My Story
Travel has always been more than a hobby for me; it is a way to truly connect with the world and discover new perspectives. I began exploring because I never wanted to look back and wonder "what if"? I wanted to see the sights, hear the music, and feel the energy of the globe firsthand.
Today, that same philosophy drives my work as a travel advisor. My journey into this industry began with a desire to help others experience that same transformative joy. I believe that every journey should be as unique as the traveler, and I am dedicated to turning your travel dreams into seamless, stress-free realities so you can focus on making memories that last a lifetime.
Travel Style
My personal travel philosophy is built on the “Grand Tour” mindset: why settle for one experience when you can have them all? I specialize in luxury, high-energy, immersive itineraries that balance activity with refined comfort. I prioritize trips that offer deep value and authentic connection. I believe in “experience-first” travel, logistically sophisticated, and high-end, yet filled with the kind of authentic local flair that makes a trip truly remarkable.
Stay connected
Reviews (7)
Venessa M.
a month ago
Kylie was instrumental in planning this trip for our entire family. We're especially appreciative of all her help in making the trip all the more special for my father-in-laws 80th Birthday celebration.
Everything was organized, efficient, and simple for us to get from Point A to B. And as promised, all the amenities and welcome gifts and offerings were provided as outline in the proposal and request.
You can trust Kylie for all your travel needs, and we look forward to the many trips we plan on booking with her in the future. Thanks again, Kylie!
Arpita P.
8 months ago
She is amazing to work with - very clear and responsive.
Ping W.
8 months ago
Booking with Kylie was stress free and easy. Kylie provided options within budget and insights that cannot be gleaned through reading reviews online. She handled private transportation booking and ensured that the communication was clear with the third party vendors. Handoffs were smooth and at no time was there confusion on the day off. Kylie also went above and beyond knowing that birthdays were being celebrated and asked the cruise ship to leave bottles of champagne in the rooms.
Luisa T.
a year ago
The communication with Kylie was great. She answered all of our questions and concerns very timely. Kylie provided us with a lot of recommendation that were useful and helpful which were very much appreciated and taken. Kylie was very friendly, professional, knowledgeable, easy to work with, she listened to our wishes in making our vacation a reality. The hotel that Kylie suggested couldn't have not been closer or more convenient to our cruise port. Looking forward in working with Kylie again in the near future!
Gregory L.
a year ago
Very responsive and attentive to my needs. Have never had this experience before.
Venessa M.
a month ago
Kylie was instrumental in planning this trip for our entire family. We're especially appreciative of all her help in making the trip all the more special for my father-in-laws 80th Birthday celebration.
Everything was organized, efficient, and simple for us to get from Point A to B. And as promised, all the amenities and welcome gifts and offerings were provided as outline in the proposal and request.
You can trust Kylie for all your travel needs, and we look forward to the many trips we plan on booking with her in the future. Thanks again, Kylie!
Arpita P.
8 months ago
She is amazing to work with - very clear and responsive.
Ping W.
8 months ago
Booking with Kylie was stress free and easy. Kylie provided options within budget and insights that cannot be gleaned through reading reviews online. She handled private transportation booking and ensured that the communication was clear with the third party vendors. Handoffs were smooth and at no time was there confusion on the day off. Kylie also went above and beyond knowing that birthdays were being celebrated and asked the cruise ship to leave bottles of champagne in the rooms.
Luisa T.
a year ago
The communication with Kylie was great. She answered all of our questions and concerns very timely. Kylie provided us with a lot of recommendation that were useful and helpful which were very much appreciated and taken. Kylie was very friendly, professional, knowledgeable, easy to work with, she listened to our wishes in making our vacation a reality. The hotel that Kylie suggested couldn't have not been closer or more convenient to our cruise port. Looking forward in working with Kylie again in the near future!
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