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I’m a travel advisor passionate about the transformative power of travel and the experiences it creates. I take the time to truly understand my clients’ interests and design personalized journeys that reflect what matters most to them. Whether you’re exploring new destinations, relaxing in nature, or enjoying the local food and wine, I’m here to craft an unforgettable experience that fits your unique vision. Let’s create a trip that not only meets but exceeds your travel dreams.
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Wine Cruises
"Our girls trip with Jenn Hilchey was absolutely phenomenal!"
Our girls trip with Jenn Hilchey was absolutely phenomenla! Me and my sister wanted a getaway to Italy, so when we saw an all girls Tuscany wine trip we knew it would be perfect! And goodness did it deliver! Jenn... read moreKaitlyn D
"Trust Jenn, we’re glad we did!"
We recently visited the Tuscan hills for a wedding then spent a few days on our own - kid free! Jenn curated a few experiences for us to which we are eternally grateful! From where to get a massage in... read moreBrittanie H
"Five stars isn’t enough! this is the travel wizard you want on your side"
Five stars isn’t enough! Our Tuscany wine trip was an absolute dream — and it’s all thanks to the incredible planning and care from Jenn. From start to finish, every detail was seamless: charming vineyard tours, perfect food and wine... read moreCindy B
"Everything was 5 star from transportation, food, and of course wine!"
I highly recommend Jenn Hilchey. She booked a trip of a lifetime for my friends and I to Italy. Everything was 5 star from transportation, food, and of course wine! Jenn was patient, kind, and attentive to everyone’s needs (which... read moreAlexis S
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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