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

Plan A Private Trip

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.

Italy

Spain

France

Portugal

Greece

Croatia

Have Somewhere Else in Mind?

My specialties are rooted in Europe, but my travel planning doesn't stop there. I also work with clients traveling to destinations around the world.

Explore Travel Beyond Europe

Come Travel With Me

Small Groups. Great Wine. Even Better Company

Barcelona & Beyond: A Taste of Catalonia September 2027

View Trip Details

Sep 06 - Sep 13 , 2027

Girl's Trip: Puglia & Matera's Dolce Vita September 2027

View Trip Details

This Month's Featured Journey

The Amalfi Coast Escape

Six nights on the Amalfi Coast with the details already thoughtfully mapped out for you: a sea-view boutique stay, private chauffeur transfers, a private day...

Explore The Itinerary

I feature a new ready-to-book private itinerary each month.

Wine Cruises

Learn More

Kind Words From My Travelers

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

Our trip was nothing short of amazing! Every detail was thoughtfully planned, and it truly exceeded our expectations. From the moment we started planning, Jenn listened carefully to everything I envisioned for this vacation and turned it into a dream... read more

Magda R

Just returned from a cruise curated by the one and only Jenn Hilchey. It was absolutely fantastic. Found her on instagram and I am so glad I did. She brought together an AMAZING group of like minded women of all... read more

Tobie O

The Travel Journal

Wine, Food, Places & Ideas For Your Next Trip.

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

Slow Travel, Done Properly: Why Boutique Stays Change Everything

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

Explore The Blog