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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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Wine Cruises
"She has an absolute passion for what she does"
Jenn Hilchey arranged what any reasonable person could call a once-in-a-lifetime adventure for my wife and me. The only thing that prevents me from calling it that is the certainty that we’ll do it again!My wife and I spent 16... read moreSean M
"Everything was exceptional, from the food, to the venues, delicious wine"
I just got back from an epic trip to S. France with host Jenn Hilchey of Travel Box International. Everything was exceptional, from the food, to the venues, delicious wines, and personal touches. I usually do all the planning for... read moreApril A
"Our girls trip with Jenn Hilchey was absolutely phenomenal!"
Our girls trip with Jenn Hilchey was absolutely phenomenla! Me and my sister wanted a getaway to Italy, so when we saw an all girls Tuscany wine trip we knew it would be perfect! And goodness did it deliver! Jenn... read moreKaitlyn D
"She's the mastermind behind creating lifelong memories."
The Honeymoon of Our Dreams — Thanks to Jenn Hilchey!My wife and I recently returned from our 22-day honeymoon in Italy, and we can confidently say it was the trip of a lifetime — all thanks to Jenn from Travel... read moreMarissa A
Hosted Trips
From the travel blog
Tuscany vs. Piedmont: Which Italian Wine Region Is Right for Your Trip?
If you're planning a wine-focused trip to Italy, chances are you've come across Tuscany and Piedmont. Both are incredible, both...
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Slow Travel, Done Properly: Why Boutique Stays Change Everything
There’s a difference between seeing a place and actually experiencing it.Most trips move quickly—city to city, hotel to hotel—fitting in...
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Why I Love Hosting Girls’ Trips—and What I’ve Learned Along the Way
Sometimes I pause and think about the women who have joined me on my trips. Women from all over the...
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Why I Fell in Love with Santa Margherita Ligure! (And You Might Too)
Santa Margherita Ligure had been on my radar for a while.You’ve probably seen the Santa Margherita wine—it’s everywhere. But here’s...
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