Hosted Trips

You’re Invited to My Favorite Table

I believe the best way to experience a region is through its flavors and its people. That’s why I design intimate, hosted trips that feel less like a "tour" and more like a journey among friends.

From the first vineyard walk to the final shared dinner, I handle the details so you can focus on the connection. Together, we’ll dive deep into the local culture, tasting world-class wines alongside the families who craft them and finding the quiet, authentic corners that make each region unique.

2027 Trips Are in the Works!

Registration for the 2027 Tuscany Girls’ Trip is now open — see below for all the details. And there’s more coming! Join the waitlist to be the first to hear about upcoming trips, destinations, and new releases.

"The trip plan exceeded all my expectations, unfolding seamlessly..."

The trip plan exceeded all my expectations, unfolding seamlessly...
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 more
Marize L

"I can’t wait to book my next trip with Jenn!"

I can’t wait to book my next trip with Jenn!
Jenn Hilchey hosted the BEST trip to Tuscany! I came across her Instagram page and decided to book a trip with her and I’m so glad I did!The trip far exceeded my expectations!Everything was thoughtfully planned from the food to... read more
Elma P

"Jenn Hilchey was an absolute dream to work with."

Jenn Hilchey was an absolute dream to work with.
Absolutely an amazing experience! Jenn Hilchey was an absolute dream to work with. Have I ever experienced anything like the trip she put together? it was a first. Hopefully, more trips to book with her. I am impressed. Class act... read more
Elle E

Exclusive Itineraries Are Coming

Join the Waitlist Today!