Jenn Hilchey

hi there!

I'm so happy you’re here!

I’m a travel advisor who believes the best trips come from experiencing a destination in a way that feels personal to you. I take the time to understand how my clients like to travel and what they’re most excited to experience, then bring it all together with the help of trusted partners around the world. From incredible food and wine to local culture, beautiful stays, and experiences you may not have discovered on your own, every trip is thoughtfully planned around you—without losing the freedom to simply enjoy where you are.

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Every Region has a Story

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Wine Cruises

"Saying it was "exceptional" hardly does it justice!"

Saying it was
I recently returned from a Tuscan wine trip with Jenn and a group of incredible women this past May, and saying it was "exceptional" hardly does it justice. It was genuinely a dream trip I could have never imagined coming... read more
Natalie D

"Jenn was born to do this."

Jenn was born to do this.
Signing up for this trip was an easy and seamless process. Jenn remained in constant and consistent contact with me. This trip/experience exceeded my expectations. Everything went as planned, the itinerary was a combination of fun activities, sightseeing and experiencing... read more
Kendra I

"Everything was exceptional, from the food, to the venues, delicious wine"

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 more
April A

"I put everything in her hands, was definitely the best trip all around!"

I put everything in her hands, was definitely the best trip all around!
Jenn Hilchey was absolutely AMAZING!!! She helped me plan a very special 46th birthday to the Bahamas. I put everything in her hands and it was definitely the best trip all around. Her advice was the best along with making... read more
Christy W

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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