hi there!
I'm so happy you’re here!
I’m a travel advisor passionate about the transformative power of travel and the experiences it creates. I take the time to truly understand my clients’ interests and design personalized journeys that reflect what matters most to them. Whether you’re exploring new destinations, relaxing in nature, or enjoying the local food and wine, I’m here to craft an unforgettable experience that fits your unique vision. Let’s create a trip that not only meets but exceeds your travel dreams.
Learn MoreEvery Region has a Story
Learn More
Wine Cruises
"If there was a way to give more than 5 stars, Jenn would get them!"
If there was a way to give more than 5 stars, Jenn would get them! Her care to planning and attention to detail is unmatched, with every part of our recent girls trip to France being amazing and every detail... read moreAshley G
"I recommend Jenn to plan an amazing trip for your next travel plans."
Jenn planned a wonderful Italy trip for my husband and I. She made all the arrangements for us with transportation and booking a tour of Pompeii and then to a winery to Cantina del vesuvio. The driver she arranged was... read moreElizabeth G
"I cannot say enough wonderful things about Jenn Hilchey"
I cannot say enough wonderful things about Jenn Hilchey and the incredible women’s solo travel experience she planned at Tenuta Torciano in Italy. From start to finish, every detail was thoughtfully arranged, creating a truly stress-free and unforgettable journey. Our itinerary... read moreSally M
"Thank you, Jenn for giving our family memories that will last a lifetime"
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 moreMagda R
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 MoreGet On The List For
Emails You'll Look Forward To!
Subscribe to receive updates on special promotions, exclusive events & announcements from us.