Debra Winke
She/Her
Based in Chicago
Debra Winke
Ask me about
My Story
Food, wine, and travel are my love language. Based in Chicago, I craft bespoke trips packed with personality, perks, and zero stress. Whether it’s a luxury getaway or a once-in-a-lifetime escape, I handle every detail so you can focus on making memories.
Travel Style
I’ve always loved travel because it lets you see the world through a different lens. I’m drawn to luxury experiences, but I also love uncovering hidden gems that make a trip truly unique. I believe every journey should include a few splurges on what matters most to you—it’s those touches that make it unforgettable.
I’m equally inspired by iconic destinations and underrated escapes, always on the hunt for the best hotels, the right perks, and incredible value. My goal is to create seamless, stress-free luxury travel that feels effortless yet extraordinary. From securing VIP perks to perfecting every detail, I do the work—you live the dream.
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Reviews (16)
Klaire K.
2 months ago
Debra was absolutely wonderful to work with. Communication was always timely, clear, and incredibly helpful throughout the entire planning process. She truly listened to our preferences and made thoughtful recommendations that elevated our trip and took the stress out of planning.
Corey J.
4 months ago
Debra is a pro, period. Her personal experiences at so many of the places she works with are a massive plus. Delightful and we will use Debra's expertise every time we travel in the future! Highly recommend!!
Dawn H.
5 months ago
This was our first experience with booking travel thru Debra & I can say this will be our only option moving forward. Debra made the planning process fun rather than clumsy & daunting…her expert opinions were priceless. Champagne region was beyond memorable & I thank Debra for making the experience perfect.
Jonathan L.
5 months ago
Debra goes above and beyond for her clients. She worked with us to find the right property that fit our budget and wishes. We love having her as our travel advisor - she always brings great ideas and makes sure we don't have to worry about details and can enjoy our travels.
Ashley B.
5 months ago
Debra was so helpful! She helped plan all our days according the location of everything. She recommended a wonderful hotel as well. She also helped booked our airport transportation to and from the hotel. This was all so helpful since we had not been to London before. Really appreciate the extra effort she put in and her tips and tricks and restaurant recommendations. Debra really helped make this a memorable trip!
Klaire K.
2 months ago
Debra was absolutely wonderful to work with. Communication was always timely, clear, and incredibly helpful throughout the entire planning process. She truly listened to our preferences and made thoughtful recommendations that elevated our trip and took the stress out of planning.
Corey J.
4 months ago
Debra is a pro, period. Her personal experiences at so many of the places she works with are a massive plus. Delightful and we will use Debra's expertise every time we travel in the future! Highly recommend!!
Dawn H.
5 months ago
This was our first experience with booking travel thru Debra & I can say this will be our only option moving forward. Debra made the planning process fun rather than clumsy & daunting…her expert opinions were priceless. Champagne region was beyond memorable & I thank Debra for making the experience perfect.
Jonathan L.
5 months ago
Debra goes above and beyond for her clients. She worked with us to find the right property that fit our budget and wishes. We love having her as our travel advisor - she always brings great ideas and makes sure we don't have to worry about details and can enjoy our travels.
Travel photos
