Small-group journeys through the world’s great wine regions, shaped by cultural history, regional food, and great company.
The Experience
By the Glass trips are built around a simple idea: wine makes more sense, and tastes better, when you understand where its origins.
That means tasting Chianti Classico in the Tuscan hills where Sangiovese has grown for centuries, not just reading about it. It means sitting down to a long lunch in a vineyard, learning what to taste and why, and having the kind of conversation that only happens when six people share a table and a good bottle. It means traveling with guides who bring both scholarly depth and genuine warmth to every stop.
Our groups are small by design, never more than six travelers. The pace is deliberate. The wine is amazing. The history is real.
Italy by the Glass — Upcoming Trip Info
March 31 to April 7, 2027
Tuscany, Emilia-Romagna, and the Veneto
Eight days through three of Italy’s most distinct wine regions, staying in a historic villa in the Chianti hills and making our way north through Bologna and the Veneto. We’ll taste Brunello, Lambrusco, Soave, Valpolicella, and Prosecco in the places where they’re made, with regional meals, wine education, and social history woven through every day.
Six travelers. One villa. A lot of great wine.
Interest List Signup
Not ready to book, but curious about what’s next?
Join our interest list and you’ll be the first to hear about upcoming By the Glass journeys, along with occasional notes on wine history, regional food culture, and the places we’re researching for future trips. Send us an email at gigi@costumersofcolor.org and ask to be on our mailing list for future trips.
About the Hosts
Chelsea Stephens, PhD is a sommelier and wine educator whose technical knowledge is matched by a genuine love for the cultural life of wine. With WSET Level 2 training and years of teaching experience, Chelsea helps travelers move past intimidation and into curiosity, learning to read a glass, understand what they’re tasting, and ask better questions at every stop along the way.
Gigi Coulson is a social scientist, public historian, and historical costumer who has spent fifteen years studying Italy through the lens of culture, community, and identity. She brings that depth to every itinerary, connecting the wine in your glass to the landscape that shaped it, the people who made it, and the long history of place that surrounds it.
Together, they offer something most wine tours don’t: the pairing of technical wine knowledge with serious cultural and historical context. One tells you what’s in the glass. The other tells you everything behind it.