Wine • Food • Culture

See Europe differently.

Private European journeys & hosted small-group trips designed around the places, flavors and experiences that make you want to stay a little longer.

Italy • France • Spain • Portugal • Greece • Croatia

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Travel with me

Hi, I'm Jenn

I plan the kind of trips I love to take.

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.

Meet Jenn

Where I Specialize

Some places I know especially well - and love sending my travelers.

United Kingdom

Australia & New Zealand

Africa

South America

Europe

United States

Wine Cruises

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"Our girls trip with Jenn Hilchey was absolutely phenomenal!"

Our girls trip with Jenn Hilchey was absolutely phenomenla! Me and my sister wanted a getaway to Italy, so when we saw an all girls Tuscany wine trip we knew it would be perfect! And goodness did it deliver! Jenn... read more

Kaitlyn D

"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

"We’re so grateful for all the care she put into this trip."

Working with Jenn was one of the best parts of planning our trip. She understood exactly what we wanted and made everything feel easy from beginning to end.She booked our cruise rooms right next to each other and arranged private... read more

Jeff G

"Trust Jenn, we’re glad we did!"

We recently visited the Tuscan hills for a wedding then spent a few days on our own - kid free! Jenn curated a few experiences for us to which we are eternally grateful! From where to get a massage in... read more

Brittanie H

Hosted Trips

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From the travel blog

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...

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...

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...

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...