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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
"Jenn was born to do this."
Signing up for this trip was an easy and seamless process. Jenn remained in constant and consistent contact with me. This trip/experience exceeded my expectations. Everything went as planned, the itinerary was a combination of fun activities, sightseeing and experiencing... read moreKendra I
"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
"Jenn somehow knew exactly what we needed before we did."
Jenn Hilchey turned my “too busy to plan” & “last minute” birthday chaos into a Tenerife dream - the best birthday getaway with my girls. Jenn has the patience of a saint, provided speed of light replies and somehow knew... read morePhebe P
"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
Hosted Trips
From the travel blog
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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Embracing the Real Turkey, A Personal Reflection
I’ve just arrived home safely and have been reflecting on my time in Turkey. I’m honestly blown away by how...
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ArtCava: A Sparkling Adventure You Won't Want to Miss!
What happens when you mix ancient history, artisan cava, and a warm, welcoming team? You get an unforgettable experience at...
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Sipping Through the Seasons: The Best Times to Visit Iconic Wine Regions
Hello, fellow wine lovers and adventure seekers! If you’re anything like me, you know that timing is everything, especially when...
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