Travel Advisor

Advisor - Caryn Ruocco

Caryn Ruocco

She/Her

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Expertise

  • Luxury,
  • Boutique Travel,
  • Mexico,
  • France,
  • Italy,
  • Greece

Based in

Chicago, IL

Profile details

About

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.

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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.

Caryn's travel guides & trip reports

Tales from Two Regions: A Luxury Journey Through Tuscany & Umbria curated by Caryn Ruocco
Guide

Tales from Two Regions: A Luxury Journey Through Tuscany & Umbria

While the cypress-lined roads of Tuscany and the rolling hills of Umbria are iconic symbols of these parts of Italy, a new wave of luxury properties is popping up in these historic Italian regions....
The Eiffel tower towering over the city of Paris.
Guide

A Sojourn Through Paris

Paris has so much to offer each and every traveler. From its many museums, historical sights, amazing hotels and delicious food and drink, you are sure to find something to satisfy even the most...
A street with buildings on both sides.
Guide

A journey through Provence

Step into the heart of the Provencal villages, where narrow cobblestone streets wind their way through markets bursting with the flavors and aromas of fresh produce, artisanal cheeses and fragrant...
A small boat docked in a body of water with buildings on land in the distance
Guide

Ischia - A Hidden Gem of Italy

Ischia is the perfect destination to explore Italy without feeling like you are surrounded by tourists. Instead, it feels like you are truly surrounded by locals. It is beautiful, authentic and full...
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Favorite hotels

Caryn's travel photos

sunset view
fields view
green valley
view of umbrellas
coast side
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Caryn's reviews

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

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 💗.

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

Excellent experience. Caryn is extremely knowledgeable of the properties she recommends and more importantly she goes above and beyond to get extra lodging benefits for her customers

Get in touch with Caryn

Reach out to customize and book your own experience. Or, just to chat about travel in general.

You can normally expect a response from Caryn within a business day or so. You’ll also be subscribed to our travel newsletter (you can unsubscribe at any time).

Advisor - Caryn Ruocco

Travel Advisor

Caryn Ruocco