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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
"Jenn is absolutely my new go to for all things travel."
Just returned from a cruise curated by the one and only Jenn Hilchey. It was absolutely fantastic. Found her on instagram and I am so glad I did. She brought together an AMAZING group of like minded women of all... read moreTobie O
"We cannot thank Jenn Hilchey enough!"
We cannot thank Jenn Hilchey enough for planning such a wonderful trip to Napa Valley! She provided numerous beautiful locations to stay that gave us great options to choose from depending on the budget we wanted to stay in, as... read moreStephanie R
"Thank you, Jenn for giving our family memories that will last a lifetime"
Our trip was nothing short of amazing! Every detail was thoughtfully planned, and it truly exceeded our expectations. From the moment we started planning, Jenn listened carefully to everything I envisioned for this vacation and turned it into a dream... read moreMagda R
"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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