Jenn Hilchey

hi there!

I'm so happy you’re here!

I’m a travel advisor passionate about the transformative power of travel and the experiences it creates. I take the time to truly understand my clients’ interests and design personalized journeys that reflect what matters most to them. Whether you’re exploring new destinations, relaxing in nature, or enjoying the local food and wine, I’m here to craft an unforgettable experience that fits your unique vision. Let’s create a trip that not only meets but exceeds your travel dreams.

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Every Region has a Story

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Wine Cruises

"Trust Jenn, we’re glad we did!"

Trust Jenn, we’re glad we did!
We recently visited the Tuscan hills for a wedding then spent a few days on our own - kid free! Jenn curated a few experiences for us to which we are eternally grateful! From where to get a massage in... read more
Brittanie H

"We had an incredible trip to Panama-thoughtfully planned by Jenn Hilchey"

We had an incredible trip to Panama-thoughtfully planned by Jenn Hilchey
We had an incredible trip to Panama, thoughtfully planned by Jenn Hilchey. From start to finish, she connected with us personally and handled every detail, booking each step with care. Her collaboration with Panama Trails and Rafael made the experience... read more
Eric J

"First international trip to Europe and we are so appreciative of Jenn"

First international trip to Europe and we are so appreciative of Jenn
The vacation of a lifetime!  My wife and mine's first international trip to Europe and we are so appreciative of Jenn Hilchey from Travel Box International for helping us to plan and execute our trip. Our cruise excursions to Mykonos, Kusadasi, Santorini,... read more
Randy F

"I would recommend Jenn over and over again."

I would recommend Jenn over and over again.
 I recently came back from a Girls Trip to Marseille, France, with Jenn. She is the absolute best! From assisting in pairing me with a roommate (I'm a solo traveler) to her thoughtful communication leading up to the trip. She... read more
Katrina G

Hosted Trips

From the travel blog

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Featured Fall Experience: Blackberry Farm, Walland, Tennessee

Featured Fall Experience: Blackberry Farm, Walland, Tennessee

Phil & Friends: November 20–23, 2025 Join Phil Rosenthal, star of Netflix’s Somebody Feed Phil, and James Beard Award-winning Chef Nancy...

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Riviera Designates World First Solo Cruise Ship

Riviera Designates World First Solo Cruise Ship

Solo travel keeps growing, and now there’s a river ship just for singletons to enjoy cruising together for the whole...

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Holiday Vacay: Why to Travel for the Holidays and Top Tips to Make it a Triumph

Holiday Vacay: Why to Travel for the Holidays and Top Tips to Make it a Triumph

The festive season is no longer just about gathering ‘round the hearth and home; it’s increasingly becoming the perfect time...

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FAQ's About the EU's New Entry System, Launching October, 2025

FAQ's About the EU's New Entry System, Launching October, 2025

Are you ready for your next trip to Europe? The European Union’s new, automated, digital entry and exit system for...

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