Hi, I'm Jenn Hilchey

I’m a travel advisor who specializes in wine travel, but I’m also someone who loves crafting experiences that bring people together—whether that’s through a great glass of wine, amazing food, or a trip that creates memories to last a lifetime.

I started my journey in the food, wine, and hospitality industry, but my passion for travel grew after experiencing firsthand how it can be one of the most powerful forms of education. Traveling opens your mind, shifts your perspective, and teaches you more about the world—and yourself—than you could ever imagine. Over the years, I’ve combined that passion with my expertise to create trips that go beyond just booking a destination. It’s about curating adventures that reflect who you are and what you love. Whether it’s a wine tour in Europe or a relaxing getaway to recharge, I make sure your trip feels personal, fun, and completely tailored to you.

When I’m not helping clients plan their next getaway, you’ll probably find me cooking, exploring new wines and destinations, or spending time with my family and friends. One of my favorite travel memories is getting engaged in Napa Valley—it’s a place that perfectly blends my love for wine, travel, and meaningful moments.

I believe in a balance of adventure and wellness, both physical and mental, which I prioritize in my own travels. If this resonates with you, I offer opportunities to incorporate wellness into your journey—whether that’s through activities like meditation, spa treatments, or simply carving out time to relax in serene settings. Whether you’re traveling solo, as a couple, or joining one of my girls’ getaways, I design trips that are tailored to your needs—whether that’s exploring a new wine region or taking time to recharge.

Let’s create a trip that feels as exciting and unforgettable as your own story.

Cheers!

"We highly recommend reaching out to Jenn Hilchey for the perfect getaway"

We highly recommend reaching out to Jenn Hilchey for the perfect getaway
An Unforgettable Honeymoon Experience!We cannot thank Jenn Hilchey enough for making our honeymoon in Dubrovnik, Croatia, absolutely magical! As huge Game of Thrones fans, we were thrilled when Jenn recommended and booked an incredible tour that took us to all... read more
Tony C

"I recommend Jenn to plan an amazing trip for your next travel plans."

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 more
Elizabeth G

"Wine Travel by Jenn Hilchey is the way to go!"

Wine Travel by Jenn Hilchey is the way to go!
If you want a seamless and memorable day trip, Wine Travel by Jenn Hilchey is the way to go! Jenn provided a variety of excursions for our honeymoon at varying price points during our time in Florence. She listed out... read more
Rebecca M

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