Jenn Hilchey

hi there!

I'm so happy you’re here!

I’m a travel advisor passionate about the transformative power of travel and the experiences it creates. I take the time to truly understand my clients’ interests and design personalized journeys that reflect what matters most to them. Whether you’re exploring new destinations, relaxing in nature, or enjoying the local food and wine, I’m here to craft an unforgettable experience that fits your unique vision. Let’s create a trip that not only meets but exceeds your travel dreams.

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Every Region has a Story

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Wine Cruises

"I recommend Jenn to plan an amazing trip for your next travel plans."

I recommend Jenn to plan an amazing trip for your next travel plans.
Jenn planned a wonderful Italy trip for my husband and I. She made all the arrangements for us with transportation and booking a tour of Pompeii and then to a winery to Cantina del vesuvio. The driver she arranged was... read more
Elizabeth G

"If you book with Jenn you will be in very good hands, she is exceptional"

If you book with Jenn you will be in very good hands, she is exceptional
I just got back from the trip of a lifetime! Jenn curated the most amazing 5 day girls wine getaway in Tuscany. When I saw it posted on instagram, I reached out…only one spot open…and I went for it! I... read more
Vickey D

"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

"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

Hosted Trips

From the travel blog

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Featured Fall Experience: Blackberry Farm, Walland, Tennessee

Featured Fall Experience: Blackberry Farm, Walland, Tennessee

Phil & Friends: November 20–23, 2025 Join Phil Rosenthal, star of Netflix’s Somebody Feed Phil, and James Beard Award-winning Chef Nancy...

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Holiday Vacay: Why to Travel for the Holidays and Top Tips to Make it a Triumph

Holiday Vacay: Why to Travel for the Holidays and Top Tips to Make it a Triumph

The festive season is no longer just about gathering ‘round the hearth and home; it’s increasingly becoming the perfect time...

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Riviera Designates World First Solo Cruise Ship

Riviera Designates World First Solo Cruise Ship

Solo travel keeps growing, and now there’s a river ship just for singletons to enjoy cruising together for the whole...

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FAQ's About the EU's New Entry System, Launching October, 2025

FAQ's About the EU's New Entry System, Launching October, 2025

Are you ready for your next trip to Europe? The European Union’s new, automated, digital entry and exit system for...

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