Travel Advisor

Cara Ruocco

She/Her

Expertise

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

Based in

Chicago, IL

Travel Advisor

Cara Ruocco

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.

Cara's travel guides & trip reports

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...

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

The Maybourne Riviera

Modern hotel overlooking the rocky peninsula of Roquebrune-Cap-Martin with luxe rooms and suites.

Fora Perks

★
$100 hotel / resort credit.
★
Breakfast daily.
★
Upgrade & extended check-in/out whenever possible.

Monastero Santa Rosa Hotel & Spa

Retreat to a heavenly sanctuary perched on the cliffs of the Amalfi Coast, where history, serenity and indulgence converge.

Fora Perks

★
$100 hotel credit.
★
Breakfast daily.
★
Upgrade & extended check-in/out whenever possible.

Rosewood Mayakoba

The most luxurious property in the Mayakoba complex, the Rosewood is emerged in deep green mangroves and serene emerald lagoons.

Fora Perks

★
$100 hotel / resort credit.
★
Breakfast daily.
★
Upgrade & extended check-in/out whenever possible.

Las Ventanas Al Paraiso, A Rosewood Resort

One of Cabo’s finest, with its distinctive Baja design and complex of pools and alfresco common spaces overlooking the sparkling Sea of Cortez.

Fora Perks

★
$100 food / beverage credit.
★
Breakfast daily.
★
Upgrade & extended check-in/out whenever possible.

Les Roches Rouges

Pack your Breton stripes for a chic stay at this seaside boutique between Nice and St. Tropez.

Hôtel de Crillon, a Rosewood Hotel

Hôtel de Crillon, a Rosewood Hotel, epitomizes luxury and history in the heart of Paris, offering an exquisite blend of elegance, modern comfort and timeless charm.

Fora Perks

★
$100 food / beverage credit.
★
Breakfast daily.
★
Upgrade & extended check-in/out whenever possible.

Cara's travel photos

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Cara's reviews

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

Ed E.
Booked travel to Playa del Carmen
March 2025

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 💗.

Ellen R.
Booked travel to Playa del Carmen
March 2025

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

Heather A.
Booked travel to Florida
February 2025

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

Daniel C.
Booked travel to Mexico
February 2025

Get in touch with Cara

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

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