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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 recommend Jenn to plan an amazing trip for your next travel plans."
Jenn planned a wonderful Italy trip for my husband and I. She made all the arrangements for us with transportation and booking a tour of Pompeii and then to a winery to Cantina del vesuvio. The driver she arranged was... read moreElizabeth G
"We couldn’t have asked for a better travel experience."
This was truly one of the most memorable trips I’ve ever taken. A huge thank you to Jenn for planning such a seamless and well-organized experience from start to finish. Every detail was thoughtfully arranged, and it was such a... read moreFatema W
"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
"I put everything in her hands, was definitely the best trip all around!"
Jenn Hilchey was absolutely AMAZING!!! She helped me plan a very special 46th birthday to the Bahamas. I put everything in her hands and it was definitely the best trip all around. Her advice was the best along with making... read moreChristy W
Hosted Trips
From the travel blog
Featured Fall Experience: Blackberry Farm, Walland, Tennessee
Phil & Friends: November 20–23, 2025 Join Phil Rosenthal, star of Netflix’s Somebody Feed Phil, and James Beard Award-winning Chef Nancy...
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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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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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