For many people, wine falls into one of two categories: intimidating or inaccessible. Tastings can feel like exams in disguise, complete with unfamiliar terminology and unspoken expectations, while more casual events often skim the surface, leaving guests entertained but not necessarily enlightened.
Molly Montgomery believes there's a better way. As founder of Bespoke Wine Journeys, she has built a business around the idea that wine is less about memorizing tasting notes and more about understanding the stories behind the glass. Through curated tastings, immersive events, and thoughtfully designed travel experiences, she invites guests to explore wine through history, culture, literature, and human connection.
"I kept running into the same two extremes," Molly says. "Wine events that felt like a test, and wine events that never went past 'this one's fruity.' I wanted to build something in between, where you could actually learn something and still feel completely at ease." That philosophy is woven throughout every Bespoke Wine Journeys experience.
Rather than leading with technical information about acidity or tannins, Molly starts somewhere far more relatable. "I always start with the story, not the spec sheet," she says. "Who made this wine, what was happening in their world at the time, why it matters. Once you care about the story, the technical side just makes sense on its own." The result is an experience that feels as much like a conversation as a class, welcoming everyone from curious beginners to seasoned wine enthusiasts.
That approach resonates particularly well in Colorado. Molly sees the Denver area as a community filled with people eager to explore without pretense. "What I love about this community is that people are genuinely curious without being hesitant about it," she says. "They're not looking for someone to tell them what to like…They want to understand it for themselves."
While iconic wine regions like Napa and Bordeaux remain popular destinations, Bespoke Wine Journeys often shines a spotlight on places that receive far less attention. Montgomery is passionate about introducing travelers to regions whose stories deserve a larger audience.
"The Republic of Georgia is the one I keep coming back to," she says. "It's the birthplace of winemaking...and they're still making wine in clay vessels the same way they always have." She also points to destinations like New York's Finger Lakes, Colorado wine country, Uruguay, and Slovenia as regions that demonstrate how wine is shaped by local people and traditions long before international acclaim arrives.
One of Bespoke's most memorable events, The Haunted Library: Summerween Wine Salon, paired wine with books, local authors, and a neighborhood bookstore in a celebration of storytelling. The evening exemplified Molly's belief that wine is often the thread connecting broader cultural experiences. "It brought together a local author, a bookshop, and wine," she says. "Story and community first, wine as the way into the story."
That emphasis on meaningful experiences extends beyond the event itself. Molly hopes guests remember more than what they tasted. "I want people to leave with a story stuck in their head, not just tasting notes," she says. "If they leave more curious than when they walked in, that's the whole point of what I do."
As Bespoke Wine Journeys continues to evolve, Molly is expanding that philosophy into new ventures. Guestwork Consulting will help businesses design memorable hospitality experiences, while Read Between the Vines will blend literary retreats with wine education in immersive destinations. The formats may change, but the mission remains remarkably consistent: create experiences where wine becomes a gateway to deeper conversations, richer travel, and lasting memories.
In the end, Bespoke Wine Journeys isn't about wine alone. It's about the people who make it, the places that shape it, and the stories that connect us to what goes into the glass.
To learn more, go to BespokeWineJourneys.com or follow on Instagram at @bespokewinejourneys.