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.

"Everything was incredibly organized from beginning to end..."

Everything was incredibly organized from beginning to end...
Jenn did an outstanding job planning our trip! Everything was incredibly organized from beginning to end, making the entire experience smooth, stress-free, and enjoyable. Her attention to detail and thoughtful planning ensured that every part of the cruise and the... read more
Joyce C

"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

"I felt well taken care of and her professionalism was on point!"

I felt well taken care of and her professionalism was on point!
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 more
Bethlehem A

Exclusive Itineraries Are Coming

Join the Waitlist Today!