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
"Trust Jenn, we’re glad we did!"
We recently visited the Tuscan hills for a wedding then spent a few days on our own - kid free! Jenn curated a few experiences for us to which we are eternally grateful! From where to get a massage in... read moreBrittanie H
"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 moreElle E
"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 moreJoyce C
"She's the mastermind behind creating lifelong memories."
The Honeymoon of Our Dreams — Thanks to Jenn Hilchey!My wife and I recently returned from our 22-day honeymoon in Italy, and we can confidently say it was the trip of a lifetime — all thanks to Jenn from Travel... read moreMarissa A
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.