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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
"I will never not use her now!"
I had the idea of visiting Portugal, mostly because my wife mentioned it as a country she really wanted to visit.So I wanted to surprise her with a fully booked family trip but I had no idea where and what... read moreChris U
"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
"Jenn went above and beyond!"
We just returned from our cruise and Jenn helped us book our excursions in Nassau and Amber Cove. She did lots of research and vetting that saved us time and landed us 2 AMAZING VIP experiences! She was in constant... read moreJennifer J
"Saying it was "exceptional" hardly does it justice!"
I recently returned from a Tuscan wine trip with Jenn and a group of incredible women this past May, and saying it was "exceptional" hardly does it justice. It was genuinely a dream trip I could have never imagined coming... read moreNatalie D
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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