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Great food, local wine, beautiful places to stay, and meaningful experiences are always at the heart of what I do. I design private trips and host small groups throughout Europe, pairing a well-planned itinerary with authentic experiences and enough free time to actually enjoy where you are.
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Wine Cruises
Kind Words From My Travelers
It’s one thing to find a good travel advisor, but it’s another thing to find a true partner who delivers a flawless experience. After a first seamless trip to Marseille, Jenn planned a trip to Istanbul and Cappadocia.From a private... read moreLisa G
Jenn at Travel Box International planned the most incredible trip of my life. From start to finish, every detail was handled seamlessly, allowing me to simply show up and enjoy. My sister and I spent five unforgettable days in Tuscany,... read moreLindsey F
Just returned from a cruise curated by the one and only Jenn Hilchey. It was absolutely fantastic. Found her on instagram and I am so glad I did. She brought together an AMAZING group of like minded women of all... read moreTobie O
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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