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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
"Honestly, this was more than a 5-star experience."
A Dreamy Tuscan Escape Curated to Perfection by Jenn HilcheyI just returned from the most unforgettable experience in Tuscany, and it’s all thanks to the incredible Jenn Hilchey. She curated an absolute dream of a wine retreat—so thoughtfully planned, flawlessly... read moreMaryAnne S
"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 moreFatema W
"Our whole trip came together better than I could have imagined"
I seriously don’t even know where to start. Planning a destination wedding is a lot, and I truly could not have done it without our coordinator Jenn. From the very beginning she was patient, organized, and always on top of... read moreJaid S
"Jenn went above and beyond!"
We just returned from our cruise and Jenn helped us book our excursions in Nassau and Amber Cove. She did lots of research and vetting that saved us time and landed us 2 AMAZING VIP experiences! She was in constant... read moreJennifer J
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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