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

"Honestly, this was more than a 5-star experience."

Honestly, this was more than a 5-star experience.
A Dreamy Tuscan Escape Curated to Perfection by Jenn HilcheyI just returned from the most unforgettable experience in Tuscany, and it’s all thanks to the incredible Jenn Hilchey. She curated an absolute dream of a wine retreat—so thoughtfully planned, flawlessly... read more
MaryAnne S

"Everything was 5 star from transportation, food, and of course wine!"

Everything was 5 star from transportation, food, and of course wine!
I highly recommend Jenn Hilchey. She booked a trip of a lifetime for my friends and I to Italy. Everything was 5 star from transportation, food, and of course wine! Jenn was patient, kind, and attentive to everyone’s needs (which... read more
Alexis S

"Jenn somehow knew exactly what we needed before we did."

Jenn somehow knew exactly what we needed before we did.
Jenn Hilchey turned my “too busy to plan” & “last minute” birthday chaos into a Tenerife dream - the best birthday getaway with my girls. Jenn has the patience of a saint, provided speed of light replies and somehow knew... read more
Phebe P

"Wine Travel by Jenn Hilchey is the way to go!"

Wine Travel by Jenn Hilchey is the way to go!
If you want a seamless and memorable day trip, Wine Travel by Jenn Hilchey is the way to go! Jenn provided a variety of excursions for our honeymoon at varying price points during our time in Florence. She listed out... read more
Rebecca M

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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