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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
"She's the mastermind behind creating lifelong memories."
The Honeymoon of Our Dreams — Thanks to Jenn Hilchey!My wife and I recently returned from our 22-day honeymoon in Italy, and we can confidently say it was the trip of a lifetime — all thanks to Jenn from Travel... read moreMarissa A
"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
"If there was a way to give more than 5 stars, Jenn would get them!"
If there was a way to give more than 5 stars, Jenn would get them! Her care to planning and attention to detail is unmatched, with every part of our recent girls trip to France being amazing and every detail... read moreAshley G
"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
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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