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.

"Jenn, thank you for cultivating such a wonderful travel experience."

Jenn, thank you for cultivating such a wonderful travel experience.
Jenn, thank you for cultivating such a wonderful travel experience.  I had an amazing time and truly appreciated all the thought, care, and effort you put into making everything so enjoyable and seamless. Your dedication to creating a welcoming and memorable... read more
Hazal L

"Jenn is absolutely my new go to for all things travel."

Jenn is absolutely my new go to for all things travel.
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

"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

Exclusive Itineraries Are Coming

Join the Waitlist Today!