Advisor - Caryn Ruocco

Caryn Ruocco

She/Her
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  • Based in icon

    Based in Chicago, IL

Ask me about

Luxury
Boutique Travel
Mexico
France
Italy
Greece

My Story

Chicago-based travel advisor specializing in curated experiences and meticulous planning. I bring your travel dreams to life with thoughtful planning and exclusive experiences. Travel deeper, explore further — be a traveler, not just a tourist.

My Travel Style

My travel style blends luxury with authenticity — seamlessly combining five-star stays, exclusive experiences and thoughtful personal touches with immersive cultural moments. I love uncovering hidden gems, curating bespoke itineraries and ensuring every trip feels effortless yet extraordinary. Whether it’s a remote island escape, a chic urban retreat or an adventure-packed journey, I believe in traveling deeper, not just checking off destinations.

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My reviews (34)

8 months ago

Caryn our travel advisor was amazing!! gracious and extremely knowledgable, coordinating wonderful private parties and excursions for our VERY large group, and always responding promptly prior to us getting there with any questions or concerns. She is someone I will gladly recommend to others and my family will definitely hope to work with her again on another travel experience! Thank you Caryn for all that you did to make this trip so memorable for our seniors (and their moms)!

8 months ago

Caryn handled all of the details of the stay in a flawless manner. She went above and beyond to make sure that everything went smoothly.

9 months ago

Caryn was a huge help getting the room booked and setting up activities! The snorkeling trip was the highlight of the week!

9 months ago

What a true gem Caryn is! She made our travel plans with professionalism, efficiency but most importantly ease. She is true delight to work with from the delicious treats she had delivered upon arrival to the check-ins to ensure our stay. Caryn surpassed any and all expectations. It's important to add that Caryn smoothly organized this trip not only for our family, but over 30 more for a spring break class trip. We collectively were so grateful for her charge, direction and care for every last detail. What a lovely holiday and beautiful memories to last a lifetime 💗.

10 months ago

Booking with Caryn Ruocco was great and super easy. We loved all of her perks especially the breakfast.

My travel ideas (5)

My travel photos

sunset view
green valley
coast side
fields view
view of umbrellas

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