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!

"If you book with Jenn you will be in very good hands, she is exceptional"

If you book with Jenn you will be in very good hands, she is exceptional
I just got back from the trip of a lifetime! Jenn curated the most amazing 5 day girls wine getaway in Tuscany. When I saw it posted on instagram, I reached out…only one spot open…and I went for it! I... read more
Vickey D

"Everything was 5 star from transportation, food, and of course wine!"

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 more
Alexis S

"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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