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!

"Jenn somehow knew exactly what we needed before we did."

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 more
Phebe P

"Jenn was born to do this."

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 more
Kendra I

"Five stars isn’t enough! this is the travel wizard you want on your side"

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 more
Cindy B

"An unforgettable STRESS FREE experience thanks to Jenn!"

An unforgettable STRESS FREE experience thanks to Jenn!
OMG!! We are so grateful and thankful to have Jenn helping us with our wine tour in Piedmont, Italy! SHE IS THE BEST! She not only recommended us with the most amazing wine tour in the area but she also... read more
Taro L

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