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 would recommend Jenn over and over again."

I would recommend Jenn over and over again.
 I recently came back from a Girls Trip to Marseille, France, with Jenn. She is the absolute best! From assisting in pairing me with a roommate (I'm a solo traveler) to her thoughtful communication leading up to the trip. She... read more
Katrina G

"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

"Look to Jenn. She is in a league of her own."

Look to Jenn. She is in a league of her own.
It’s one thing to find a good travel advisor, but it’s another thing to find a true partner who delivers a flawless experience. After a first seamless trip to Marseille, Jenn planned a trip to Istanbul and Cappadocia.From a private... read more
Lisa G

"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

Hosted Trips

From the travel blog

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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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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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