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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
"I can’t wait to book my next trip with Jenn!"
Jenn Hilchey hosted the BEST trip to Tuscany! I came across her Instagram page and decided to book a trip with her and I’m so glad I did!The trip far exceeded my expectations!Everything was thoughtfully planned from the food to... read moreElma P
"First international trip to Europe and we are so appreciative of Jenn"
The vacation of a lifetime! My wife and mine's first international trip to Europe and we are so appreciative of Jenn Hilchey from Travel Box International for helping us to plan and execute our trip. Our cruise excursions to Mykonos, Kusadasi, Santorini,... read moreRandy F
"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
Hosted Trips
From the travel blog
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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Embracing the Real Turkey, A Personal Reflection
I’ve just arrived home safely and have been reflecting on my time in Turkey. I’m honestly blown away by how...
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