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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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Wine Cruises
"Highly recommend you book through Jenn for any travel US/International"
What an amazing adventure with Jenn Hilchey 🇮🇹 Jenn is an amazing person. Her energy is like no other. If you have a question, she's there with an answer and always so helpful. This 'Girls Trip' to Tuscany exceeded my... read moreJin W
"We’re so grateful for all the care she put into this trip."
Working with Jenn was one of the best parts of planning our trip. She understood exactly what we wanted and made everything feel easy from beginning to end.She booked our cruise rooms right next to each other and arranged private... read moreJeff G
"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 moreBrittanie H
"She has an absolute passion for what she does"
Jenn Hilchey arranged what any reasonable person could call a once-in-a-lifetime adventure for my wife and me. The only thing that prevents me from calling it that is the certainty that we’ll do it again!My wife and I spent 16... read moreSean M
Hosted Trips
From the travel blog
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
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
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)
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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