Hi, I'm Jenn Hilchey

I’m a travel advisor based in Tampa, Florida, specializing in wine and culture-driven travel experiences around the world. My passion lies in crafting trips that bring people together—whether that’s through a shared love of great wine, local cuisine, or moments that linger long after the journey ends.

I started my career in the food, wine, and hospitality industries, where I learned that the best experiences are about connection, the kind that happens over a meal, a glass of wine, or a view you’ll never forget. That same belief guides the way I plan travel today. For me, it’s not just about where you go, but how the experience makes you feel.

Travel has always been one of my greatest teachers. It opens your mind, reshapes your perspective, and reminds you what matters most. I bring that same curiosity and care to every trip I design, whether it’s a private wine-infused itinerary through Europe, a couples’ getaway, or one of my hosted group trips.

When I’m not designing trips, you’ll find me spending time with my husband, experimenting in the kitchen with wine, sharing laughs with friends and family, or hanging out with our dogs here in Tampa. I travel often, to stay connected with the destinations and partners I recommend and to experience them as a traveler, not just an advisor, because I believe firsthand experience is what allows me to create something truly personalized for every client.

Travel should excite you, but it should also leave you feeling restored. I help my clients find that sweet spot on every journey.

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

Cheers!