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

"We couldn’t have asked for a better travel experience."

We couldn’t have asked for a better travel experience.
This was truly one of the most memorable trips I’ve ever taken. A huge thank you to Jenn for planning such a seamless and well-organized experience from start to finish. Every detail was thoughtfully arranged, and it was such a... read more
Fatema W

"An unforgettable STRESS FREE experience thanks to Jenn!"

An unforgettable STRESS FREE experience thanks to Jenn!
OMG!! We are so grateful and thankful to have Jenn helping us with our wine tour in Piedmont, Italy! SHE IS THE BEST! She not only recommended us with the most amazing wine tour in the area but she also... read more
Taro L

"If you book with Jenn you will be in very good hands, she is exceptional"

If you book with Jenn you will be in very good hands, she is exceptional
I just got back from the trip of a lifetime! Jenn curated the most amazing 5 day girls wine getaway in Tuscany. When I saw it posted on instagram, I reached out…only one spot open…and I went for it! I... read more
Vickey D

"Jenn planned the most incredible trip of my life."

Jenn planned the most incredible trip of my life.
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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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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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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Embracing the Real Turkey, A Personal Reflection

Embracing the Real Turkey, A Personal Reflection

I’ve just arrived home safely and have been reflecting on my time in Turkey. I’m honestly blown away by how...

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