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 highly recommend reaching out to Jenn Hilchey for the perfect getaway"

We highly recommend reaching out to Jenn Hilchey for the perfect getaway
An Unforgettable Honeymoon Experience!We cannot thank Jenn Hilchey enough for making our honeymoon in Dubrovnik, Croatia, absolutely magical! As huge Game of Thrones fans, we were thrilled when Jenn recommended and booked an incredible tour that took us to all... read more
Tony C

"She has an absolute passion for what she does"

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 more
Sean M

"We’re so grateful for all the care she put into this trip."

We’re so grateful for all the care she put into this trip.
Working with Jenn was one of the best parts of planning our trip. She understood exactly what we wanted and made everything feel easy from beginning to end.She booked our cruise rooms right next to each other and arranged private... read more
Jeff G

"She's the mastermind behind creating lifelong memories."

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 more
Marissa A

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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