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I'm so happy you’re here!
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 felt well taken care of and her professionalism was on point!"
If you like discovering what a Women’s retreat means in Europe choose Jenn. I chose her for my Italy retreat and it was epic. What a best choice! From welcoming lunch at Florence and doing a little site see, everything... read moreBethlehem A
"An unforgettable STRESS FREE experience thanks to Jenn!"
OMG!! We are so grateful and thankful to have Jenn helping us with our wine tour in Piedmont, Italy! SHE IS THE BEST! She not only recommended us with the most amazing wine tour in the area but she also... read moreTaro L
"Jenn is absolutely my new go to for all things travel."
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
"We had an incredible trip to Panama-thoughtfully planned by Jenn Hilchey"
We had an incredible trip to Panama, thoughtfully planned by Jenn Hilchey. From start to finish, she connected with us personally and handled every detail, booking each step with care. Her collaboration with Panama Trails and Rafael made the experience... read moreEric J
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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