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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
"She's the mastermind behind creating lifelong memories."
The Honeymoon of Our Dreams — Thanks to Jenn Hilchey!My wife and I recently returned from our 22-day honeymoon in Italy, and we can confidently say it was the trip of a lifetime — all thanks to Jenn from Travel... read moreMarissa A
"We’re so grateful for all the care she put into this trip."
Working with Jenn was one of the best parts of planning our trip. She understood exactly what we wanted and made everything feel easy from beginning to end.She booked our cruise rooms right next to each other and arranged private... read moreJeff G
"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
"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
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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