hi there!
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
"Jenn, thank you for cultivating such a wonderful travel experience."
Jenn, thank you for cultivating such a wonderful travel experience. I had an amazing time and truly appreciated all the thought, care, and effort you put into making everything so enjoyable and seamless. Your dedication to creating a welcoming and memorable... read moreHazal L
"If you are looking to travel I highly recommend working with Jenn!"
Jenn went ABOVE & BEYOND to make this the best girls trip ever! From the moment I showed interest and committed she made sure I knew the plan, helped coordinate all of my travel (flights, trains, hotels, dinner reservations and... read moreLaura L
"Jenn Hilchey was an absolute dream to work with."
Absolutely an amazing experience! Jenn Hilchey was an absolute dream to work with. Have I ever experienced anything like the trip she put together? it was a first. Hopefully, more trips to book with her. I am impressed. Class act... read moreElle E
"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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