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.

"She's the mastermind behind creating lifelong memories."

She's the mastermind behind creating lifelong memories.
The Honeymoon of Our Dreams — Thanks to Jenn Hilchey!My wife and I recently returned from our 22-day honeymoon in Italy, and we can confidently say it was the trip of a lifetime — all thanks to Jenn from Travel... read more
Marissa A

"Jenn, thank you for cultivating such a wonderful travel experience."

Jenn, thank you for cultivating such a wonderful travel experience.
Jenn, thank you for cultivating such a wonderful travel experience.  I had an amazing time and truly appreciated all the thought, care, and effort you put into making everything so enjoyable and seamless. Your dedication to creating a welcoming and memorable... read more
Hazal L

"Jenn planned the most incredible trip of my life."

Jenn planned the most incredible trip of my life.
Jenn at Travel Box International planned the most incredible trip of my life. From start to finish, every detail was handled seamlessly, allowing me to simply show up and enjoy. My sister and I spent five unforgettable days in Tuscany,... read more
Lindsey F

"Everything was incredibly organized from beginning to end..."

Everything was incredibly organized from beginning to end...
Jenn did an outstanding job planning our trip! Everything was incredibly organized from beginning to end, making the entire experience smooth, stress-free, and enjoyable. Her attention to detail and thoughtful planning ensured that every part of the cruise and the... read more
Joyce C

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