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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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Wine Cruises
"I recommend Jenn to plan an amazing trip for your next travel plans."
Jenn planned a wonderful Italy trip for my husband and I. She made all the arrangements for us with transportation and booking a tour of Pompeii and then to a winery to Cantina del vesuvio. The driver she arranged was... read moreElizabeth G
"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
"Our girls trip with Jenn Hilchey was absolutely phenomenal!"
Our girls trip with Jenn Hilchey was absolutely phenomenla! Me and my sister wanted a getaway to Italy, so when we saw an all girls Tuscany wine trip we knew it would be perfect! And goodness did it deliver! Jenn... read moreKaitlyn D
"The trip plan exceeded all my expectations, unfolding seamlessly..."
There are truly no words to capture how essential it was for me to travel to Italy and experience an unforgettable girls' trip. From the moment the idea of visiting Italy crossed my mind, I felt a mix of excitement... read moreMarize 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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