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.
Learn MoreEvery Region has a Story
Learn More
Wine Cruises
Kind Words From My Travelers
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 moreCindy B
If you like discovering what a Women’s retreat means in Europe choose Jenn. I chose her for my Italy retreat and it was epic. What a best choice! From welcoming lunch at Florence and doing a little site see, everything... read moreBethlehem A
There are truly no words to capture how essential it was for me to travel to Italy and experience an unforgettable girls' trip. From the moment the idea of visiting Italy crossed my mind, I felt a mix of excitement... read moreMarize L
Jenn Hilchey was absolutely AMAZING!!! She helped me plan a very special 46th birthday to the Bahamas. I put everything in her hands and it was definitely the best trip all around. Her advice was the best along with making... read moreChristy W
Hosted Trips
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...
Read More
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...
Read More
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...
Read More
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...
Read MoreLet's Plan Something Beautiful
Get destination inspiration, travel tips and early access to hosted trips.