Upcoming Wine Country Retreats
Dreaming of an escape to wine country? Come along with me to some of my favorite wine regions in the world. These small-group tours are perfect for anyone looking for unforgettable wine experiences, without having the stress of planning. My wine and food retreats are designed so all you have to do is pack your bags and book your flights—every detail is planned, from dreamy vineyard stays to boutique winery visits, local food experiences, and historical tours through charming small towns. I also partner with locals in the region to help organize these trips and ensure we’re discovering authentic experiences we otherwise wouldn’t have.
Come for the wine, stay for the unforgettable memories and connections that will last a lifetime.
Solo travelers are welcome too!
Sicily, Italy
April 8-13, 2026
Join me on Italy’s most vibrant island for a wine and food retreat. For this trip, I’ve partnered with Sicilian wine expert and tour guide, Helen Bezane, who specializes in sharing hidden gems of Sicily's stunning wine regions with a focus on small-production, family-owned wineries.
April is the perfect time to visit Sicily, with temperate weather, less crowds, and lower airfare costs. We'll be staying in boutique accommodations and exploring two important wine regions of Sicily, Etna and Val di Noto, as well as touring the must-visit towns of Taormina, Catania, Ortigia, Syracuse, and more.
This trip includes visits to boutique wineries, food tours through Sicily’s historic towns, a hands-on cooking class in a traditional Sicilian home, and more, all set against the stunning backdrop of Europe’s tallest active volcano and Sicily’s incredible coastline.
Find more information about this trip here or join the waitlist below. Spots will open on a first come, first served basis.
Tuscany, Italy
Fall 2026 (dates TBD)
You’re invited to join my third annual wine retreat to Tuscany! This trip is truly magical — from our private villa overlooking the rolling hills of Umbria, to boutique winery visits, truffle hunting, a cooking class, and more.
We start each day with wine tasting in unique appellations across Tuscany, followed by historical tours of Italy’s most iconic hilltop towns—Montepulciano, Siena, Pienza, and more—and we end each night with sunset aperitvo and a chef-cooked meal at our private villa (paired with plenty of local wine, of course).
"We had an awesome time! Everything was so thoughtfully curated - we enjoyed it all. This trip filled my heart with so much joy."
This trip always sells out quickly, so get your name on the waitlist to receive more information as soon as our 2026 dates are secured. Spots will open on a first come, first served basis.