Jenn Hilchey

hi there!

I'm so happy you’re here!

I’m a travel advisor who believes the best trips come from experiencing a destination in a way that feels personal to you. I take the time to understand how my clients like to travel and what they’re most excited to experience, then bring it all together with the help of trusted partners around the world. From incredible food and wine to local culture, beautiful stays, and experiences you may not have discovered on your own, every trip is thoughtfully planned around you—without losing the freedom to simply enjoy where you are.

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Every Region has a Story

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Wine Cruises

"Saying it was "exceptional" hardly does it justice!"

Saying it was
I recently returned from a Tuscan wine trip with Jenn and a group of incredible women this past May, and saying it was "exceptional" hardly does it justice. It was genuinely a dream trip I could have never imagined coming... read more
Natalie D

"Our whole trip came together better than I could have imagined"

Our whole trip came together better than I could have imagined
I seriously don’t even know where to start. Planning a destination wedding is a lot, and I truly could not have done it without our coordinator Jenn. From the very beginning she was patient, organized, and always on top of... read more
Jaid S

"Five stars isn’t enough! this is the travel wizard you want on your side"

Five stars isn’t enough! this is the travel wizard you want on your side
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

"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

Hosted Trips

From the travel blog

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Tuscany vs. Piedmont: Which Italian Wine Region Is Right for Your Trip?

Tuscany vs. Piedmont: Which Italian Wine Region Is Right for Your Trip?

If you're planning a wine-focused trip to Italy, chances are you've come across Tuscany and Piedmont. Both are incredible, both...

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Slow Travel, Done Properly: Why Boutique Stays Change Everything

Slow Travel, Done Properly: Why Boutique Stays Change Everything

There’s a difference between seeing a place and actually experiencing it.Most trips move quickly—city to city, hotel to hotel—fitting in...

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Why I Love Hosting Girls’ Trips—and What I’ve Learned Along the Way

Why I Love Hosting Girls’ Trips—and What I’ve Learned Along the Way

Sometimes I pause and think about the women who have joined me on my trips. Women from all over the...

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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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