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

"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

"Jenn somehow knew exactly what we needed before we did."

Jenn somehow knew exactly what we needed before we did.
Jenn Hilchey turned my “too busy to plan” & “last minute” birthday chaos into a Tenerife dream - the best birthday getaway with my girls. Jenn has the patience of a saint, provided speed of light replies and somehow knew... read more
Phebe P

"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

Hosted Trips

From the travel blog

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Why I Fell in Love with Santa Margherita Ligure! (And You Might Too)

Why I Fell in Love with Santa Margherita Ligure! (And You Might Too)

Santa Margherita Ligure had been on my radar for a while.You’ve probably seen the Santa Margherita wine—it’s everywhere. But here’s...

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Embracing the Real Turkey, A Personal Reflection

Embracing the Real Turkey, A Personal Reflection

I’ve just arrived home safely and have been reflecting on my time in Turkey. I’m honestly blown away by how...

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ArtCava: A Sparkling Adventure You Won't Want to Miss!

ArtCava: A Sparkling Adventure You Won't Want to Miss!

What happens when you mix ancient history, artisan cava, and a warm, welcoming team? You get an unforgettable experience at...

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Sipping Through the Seasons: The Best Times to Visit Iconic Wine Regions

Sipping Through the Seasons: The Best Times to Visit Iconic Wine Regions

Hello, fellow wine lovers and adventure seekers! If you’re anything like me, you know that timing is everything, especially when...

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