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

"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

"If you are looking to travel I highly recommend working with Jenn!"

If you are looking to travel I highly recommend working with Jenn!
Jenn went ABOVE & BEYOND to make this the best girls trip ever! From the moment I showed interest and committed she made sure I knew the plan, helped coordinate all of my travel (flights, trains, hotels, dinner reservations and... read more
Laura L

"Honestly, this was more than a 5-star experience."

Honestly, this was more than a 5-star experience.
A Dreamy Tuscan Escape Curated to Perfection by Jenn HilcheyI just returned from the most unforgettable experience in Tuscany, and it’s all thanks to the incredible Jenn Hilchey. She curated an absolute dream of a wine retreat—so thoughtfully planned, flawlessly... read more
MaryAnne S

"We couldn’t have asked for a better travel experience."

We couldn’t have asked for a better travel experience.
This was truly one of the most memorable trips I’ve ever taken. A huge thank you to Jenn for planning such a seamless and well-organized experience from start to finish. Every detail was thoughtfully arranged, and it was such a... read more
Fatema W

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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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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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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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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