Hi, I'm Jenn Hilchey

Travel advisor and group travel host based in Tampa, Florida. I design private trips and personally host small groups, with a focus on Europe and a love for exploring through food, wine, and local culture.

My 15+ years in food, wine, and hospitality shape how I care for my travelers—from understanding what you enjoy to anticipating the details you might never think to ask about. I travel often, building firsthand knowledge and relationships with local guides, hoteliers, chefs, winemakers, and travel partners who help me bring a destination to life for you.

Whether you’re planning a getaway of your own or joining a trip I’m hosting, you’ll have my experience, personal attention, and enthusiasm behind the plans. I love introducing people to places that have meant something to me—and helping them find their own reasons to return.

Kind Words From My Travelers

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
Jenn Hilchey arranged what any reasonable person could call a once-in-a-lifetime adventure for my wife and me. The only thing that prevents me from calling it that is the certainty that we’ll do it again!My wife and I spent 16... read more
Sean M
I had the idea of visiting Portugal, mostly because my wife mentioned it as a country she really wanted to visit.So I wanted to surprise her with a fully booked family trip but I had no idea where and what... read more
Chris U
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 more
Ashley G

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