
Caryn Ruocco
She/HerBased in Chicago, IL
Caryn Ruocco
Ask me about
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.
My reviews (34)
Gina D.
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)!
Adela Z.
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!
Ellen R.
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 💗.
Heather A.
10 months ago
Booking with Caryn Ruocco was great and super easy. We loved all of her perks especially the breakfast.
Gina D.
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)!
Adela Z.
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!
Ellen R.
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 💗.
My travel ideas (5)

Campus Tours, Elevated: Where to Stay, Eat & Explore on Your College Visit
College visits are a rite of passage, but they can also be an opportunity to explore new cities, bond with your teen, and enjoy a little travel fun along the way. Whether you're kicking off the college search or visiting campuses after acceptance letters roll in, thoughtful planning can make these trips both productive and memorable. Here are some of my favorite travel tips—and hotel picks—to help you make the most of your college visit travel.

Campus Tours, Elevated: Where to Stay, Eat & Explore on Your College Visit
College visits are a rite of passage, but they can also be an opportunity to explore new cities, bond with your teen, and enjoy a little travel fun along the way. Whether you're kicking off the college search or visiting campuses after acceptance letters roll in, thoughtful planning can make these trips both productive and memorable. Here are some of my favorite travel tips—and hotel picks—to help you make the most of your college visit travel.

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. Beyond the bustling streets of Florence and the familiar charm of the Tuscan wine estates lies a more intimate way to experience this magical landscape. These properties, each with its own distinct personality, do a beautiful job of blending original architecture with contemporary luxury, offering experiences that feel truly authentic.

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. Beyond the bustling streets of Florence and the familiar charm of the Tuscan wine estates lies a more intimate way to experience this magical landscape. These properties, each with its own distinct personality, do a beautiful job of blending original architecture with contemporary luxury, offering experiences that feel truly authentic.

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 discerning traveler.

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 discerning traveler.

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 herbs. The vibrant colors of local markets and the timeless architecture comes alive through the towns of Provence. Provence is more than a geographical location; it's a canvas painted with hues of lavender fields, olive groves and azure skies.

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 herbs. The vibrant colors of local markets and the timeless architecture comes alive through the towns of Provence. Provence is more than a geographical location; it's a canvas painted with hues of lavender fields, olive groves and azure skies.

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 of things to do. It's also larger than its well-known neighbor, Capri.

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 of things to do. It's also larger than its well-known neighbor, Capri.

Campus Tours, Elevated: Where to Stay, Eat & Explore on Your College Visit
College visits are a rite of passage, but they can also be an opportunity to explore new cities, bond with your teen, and enjoy a little travel fun along the way. Whether you're kicking off the college search or visiting campuses after acceptance letters roll in, thoughtful planning can make these trips both productive and memorable. Here are some of my favorite travel tips—and hotel picks—to help you make the most of your college visit travel.

Campus Tours, Elevated: Where to Stay, Eat & Explore on Your College Visit
College visits are a rite of passage, but they can also be an opportunity to explore new cities, bond with your teen, and enjoy a little travel fun along the way. Whether you're kicking off the college search or visiting campuses after acceptance letters roll in, thoughtful planning can make these trips both productive and memorable. Here are some of my favorite travel tips—and hotel picks—to help you make the most of your college visit travel.

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. Beyond the bustling streets of Florence and the familiar charm of the Tuscan wine estates lies a more intimate way to experience this magical landscape. These properties, each with its own distinct personality, do a beautiful job of blending original architecture with contemporary luxury, offering experiences that feel truly authentic.

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. Beyond the bustling streets of Florence and the familiar charm of the Tuscan wine estates lies a more intimate way to experience this magical landscape. These properties, each with its own distinct personality, do a beautiful job of blending original architecture with contemporary luxury, offering experiences that feel truly authentic.

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 discerning traveler.

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 discerning traveler.
My travel photos




