Jenn Hilchey

hi there!

I'm so happy you’re here!

I’m a travel advisor who believes the best trips come from experiencing a destination in a way that feels personal to you. I take the time to understand how my clients like to travel and what they’re most excited to experience, then bring it all together with the help of trusted partners around the world. From incredible food and wine to local culture, beautiful stays, and experiences you may not have discovered on your own, every trip is thoughtfully planned around you—without losing the freedom to simply enjoy where you are.

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Every Region has a Story

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Wine Cruises

"The excursions were spectacular and unique..."

The excursions were spectacular and unique...
I loved the women’s trip Jenn hosted on Virgin Voyages. It was my first cruise and she answered all my questions. I met amazing people and made new friends. The excursions were spectacular and unique. I will be booking another... read more
Sarah S

"Jenn was born to do this."

Jenn was born to do this.
Signing up for this trip was an easy and seamless process. Jenn remained in constant and consistent contact with me. This trip/experience exceeded my expectations. Everything went as planned, the itinerary was a combination of fun activities, sightseeing and experiencing... read more
Kendra I

"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

"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

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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