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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
"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
"I will never not use her now!"
I had the idea of visiting Portugal, mostly because my wife mentioned it as a country she really wanted to visit.So I wanted to surprise her with a fully booked family trip but I had no idea where and what... read moreChris U
"Wine Travel by Jenn Hilchey is the way to go!"
If you want a seamless and memorable day trip, Wine Travel by Jenn Hilchey is the way to go! Jenn provided a variety of excursions for our honeymoon at varying price points during our time in Florence. She listed out... read moreRebecca M
"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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