Meet Jenn

hi there!

I'm so happy you’re here!

Great food, local wine, beautiful places to stay, and meaningful experiences are always at the heart of what I do. I design private trips and host small groups throughout Europe, pairing a well-planned itinerary with authentic experiences and enough free time to actually enjoy where you are.

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Every Region has a Story

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Wine Cruises

Kind Words From My Travelers

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
What an amazing adventure with Jenn Hilchey 🇮🇹 Jenn is an amazing person. Her energy is like no other. If you have a question, she's there with an answer and always so helpful. This 'Girls Trip' to Tuscany exceeded my... read more
Jin W
If there was a way to give more than 5 stars, Jenn would get them! Her care to planning and attention to detail is unmatched, with every part of our recent girls trip to France being amazing and every detail... read more
Ashley G
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

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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Let's Plan Something Beautiful

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