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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
"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
"Thank you, Jenn for giving our family memories that will last a lifetime"
Our trip was nothing short of amazing! Every detail was thoughtfully planned, and it truly exceeded our expectations. From the moment we started planning, Jenn listened carefully to everything I envisioned for this vacation and turned it into a dream... read moreMagda R
"We couldn’t have asked for a better travel experience."
This was truly one of the most memorable trips I’ve ever taken. A huge thank you to Jenn for planning such a seamless and well-organized experience from start to finish. Every detail was thoughtfully arranged, and it was such a... read moreFatema W
"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
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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