Meet Jenn

hi there!

I'm so happy you’re here!

Great food, local wine, beautiful places to stay, and meaningful experiences are always at the heart of what I do. I design private trips and host small groups throughout Europe, pairing a well-planned itinerary with authentic experiences and enough free time to actually enjoy where you are.

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Every Region has a Story

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Wine Cruises

Kind Words From My Travelers

Five stars isn’t enough! Our Tuscany wine trip was an absolute dream — and it’s all thanks to the incredible planning and care from Jenn. From start to finish, every detail was seamless: charming vineyard tours, perfect food and wine... read more
Cindy B
There are truly no words to capture how essential it was for me to travel to Italy and experience an unforgettable girls' trip. From the moment the idea of visiting Italy crossed my mind, I felt a mix of excitement... read more
Marize L
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 more
April A
Jenn at Travel Box International planned the most incredible trip of my life. From start to finish, every detail was handled seamlessly, allowing me to simply show up and enjoy. My sister and I spent five unforgettable days in Tuscany,... read more
Lindsey F

Hosted Trips

From the travel blog

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Tuscany vs. Piedmont: Which Italian Wine Region Is Right for Your Trip?

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

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

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)

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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Let's Plan Something Beautiful

Get destination inspiration, travel tips and early access to hosted trips.