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 will never not use her now!"

I will never not use her now!
I had the idea of visiting Portugal, mostly because my wife mentioned it as a country she really wanted to visit.So I wanted to surprise her with a fully booked family trip but I had no idea where and what... read more
Chris U

"If there was a way to give more than 5 stars, Jenn would get them!"

If there was a way to give more than 5 stars, Jenn would get them!
If there was a way to give more than 5 stars, Jenn would get them! Her care to planning and attention to detail is unmatched, with every part of our recent girls trip to France being amazing and every detail... read more
Ashley G

"The trip plan exceeded all my expectations, unfolding seamlessly..."

The trip plan exceeded all my expectations, unfolding seamlessly...
There are truly no words to capture how essential it was for me to travel to Italy and experience an unforgettable girls' trip. From the moment the idea of visiting Italy crossed my mind, I felt a mix of excitement... read more
Marize L

"Thank you, Jenn for giving our family memories that will last a lifetime"

Thank you, Jenn for giving our family memories that will last a lifetime
Our trip was nothing short of amazing! Every detail was thoughtfully planned, and it truly exceeded our expectations. From the moment we started planning, Jenn listened carefully to everything I envisioned for this vacation and turned it into a dream... read more
Magda R

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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