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

What an amazing adventure with Jenn Hilchey 🇮🇹 Jenn is an amazing person. Her energy is like no other. If you have a question, she's there with an answer and always so helpful. This 'Girls Trip' to Tuscany exceeded my... read more
Jin W
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
Our girls trip with Jenn Hilchey was absolutely phenomenla! Me and my sister wanted a getaway to Italy, so when we saw an all girls Tuscany wine trip we knew it would be perfect! And goodness did it deliver! Jenn... read more
Kaitlyn D

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