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

"I recommend Jenn to plan an amazing trip for your next travel plans."

I recommend Jenn to plan an amazing trip for your next travel plans.
Jenn planned a wonderful Italy trip for my husband and I. She made all the arrangements for us with transportation and booking a tour of Pompeii and then to a winery to Cantina del vesuvio. The driver she arranged was... read more
Elizabeth G

"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

"If you are looking to travel I highly recommend working with Jenn!"

If you are looking to travel I highly recommend working with Jenn!
Jenn went ABOVE & BEYOND to make this the best girls trip ever! From the moment I showed interest and committed she made sure I knew the plan, helped coordinate all of my travel (flights, trains, hotels, dinner reservations and... read more
Laura L

"Five stars isn’t enough! this is the travel wizard you want on your side"

Five stars isn’t enough! this is the travel wizard you want on your side
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

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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