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

"Trust Jenn, we’re glad we did!"

Trust Jenn, we’re glad we did!
We recently visited the Tuscan hills for a wedding then spent a few days on our own - kid free! Jenn curated a few experiences for us to which we are eternally grateful! From where to get a massage in... read more
Brittanie H

"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

"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

"We couldn’t have asked for a better travel experience."

We couldn’t have asked for a better travel experience.
This was truly one of the most memorable trips I’ve ever taken. A huge thank you to Jenn for planning such a seamless and well-organized experience from start to finish. Every detail was thoughtfully arranged, and it was such a... read more
Fatema W

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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