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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
"Everything was exceptional, from the food, to the venues, delicious wine"
I just got back from an epic trip to S. France with host Jenn Hilchey of Travel Box International. Everything was exceptional, from the food, to the venues, delicious wines, and personal touches. I usually do all the planning for... read moreApril A
"If you book with Jenn you will be in very good hands, she is exceptional"
I just got back from the trip of a lifetime! Jenn curated the most amazing 5 day girls wine getaway in Tuscany. When I saw it posted on instagram, I reached out…only one spot open…and I went for it! I... read moreVickey D
"Highly recommend you book through Jenn for any travel US/International"
What an amazing adventure with Jenn Hilchey 🇮🇹 Jenn is an amazing person. Her energy is like no other. If you have a question, she's there with an answer and always so helpful. This 'Girls Trip' to Tuscany exceeded my... read moreJin W
"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
Hosted Trips
From the travel blog
Featured Fall Experience: Blackberry Farm, Walland, Tennessee
Phil & Friends: November 20–23, 2025 Join Phil Rosenthal, star of Netflix’s Somebody Feed Phil, and James Beard Award-winning Chef Nancy...
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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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