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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 highly recommend reaching out to Jenn Hilchey for the perfect getaway"
An Unforgettable Honeymoon Experience!We cannot thank Jenn Hilchey enough for making our honeymoon in Dubrovnik, Croatia, absolutely magical! As huge Game of Thrones fans, we were thrilled when Jenn recommended and booked an incredible tour that took us to all... read moreTony C
"Jenn Hilchey was an absolute dream to work with."
Absolutely an amazing experience! Jenn Hilchey was an absolute dream to work with. Have I ever experienced anything like the trip she put together? it was a first. Hopefully, more trips to book with her. I am impressed. Class act... read moreElle E
"Jenn, thank you for cultivating such a wonderful travel experience."
Jenn, thank you for cultivating such a wonderful travel experience. I had an amazing time and truly appreciated all the thought, care, and effort you put into making everything so enjoyable and seamless. Your dedication to creating a welcoming and memorable... read moreHazal L
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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