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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
"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
"I cannot say enough wonderful things about Jenn Hilchey"
I cannot say enough wonderful things about Jenn Hilchey and the incredible women’s solo travel experience she planned at Tenuta Torciano in Italy. From start to finish, every detail was thoughtfully arranged, creating a truly stress-free and unforgettable journey. Our itinerary... read moreSally M
"We had an incredible trip to Panama-thoughtfully planned by Jenn Hilchey"
We had an incredible trip to Panama, thoughtfully planned by Jenn Hilchey. From start to finish, she connected with us personally and handled every detail, booking each step with care. Her collaboration with Panama Trails and Rafael made the experience... read moreEric J
"I would recommend Jenn over and over again."
I recently came back from a Girls Trip to Marseille, France, with Jenn. She is the absolute best! From assisting in pairing me with a roommate (I'm a solo traveler) to her thoughtful communication leading up to the trip. She... read moreKatrina G
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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