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
"We couldn’t have asked for a better travel experience."
This was truly one of the most memorable trips I’ve ever taken. A huge thank you to Jenn for planning such a seamless and well-organized experience from start to finish. Every detail was thoughtfully arranged, and it was such a... read moreFatema W
"An unforgettable STRESS FREE experience thanks to Jenn!"
OMG!! We are so grateful and thankful to have Jenn helping us with our wine tour in Piedmont, Italy! SHE IS THE BEST! She not only recommended us with the most amazing wine tour in the area but she also... read moreTaro L
"Highly recommend you book through Jenn for any travel US/International"
What an amazing adventure with Jenn Hilchey 🇮🇹 Jenn is an amazing person. Her energy is like no other. If you have a question, she's there with an answer and always so helpful. This 'Girls Trip' to Tuscany exceeded my... read moreJin W
"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
Hosted Trips
From the travel blog
Featured Fall Experience: Blackberry Farm, Walland, Tennessee
Phil & Friends: November 20–23, 2025 Join Phil Rosenthal, star of Netflix’s Somebody Feed Phil, and James Beard Award-winning Chef Nancy...
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 More
Embracing the Real Turkey, A Personal Reflection
I’ve just arrived home safely and have been reflecting on my time in Turkey. I’m honestly blown away by how...
Read MoreGet On The List For
Emails You'll Look Forward To!
Subscribe to receive updates on special promotions, exclusive events & announcements from us.