JACKIE FLAHERTY founded The Weekend Discovery with the vision that one of life’s greatest joys—travel—should never be overwhelming or out of reach. From milestone celebrations and multigenerational getaways to elaborate European itineraries and cruises, Flaherty and her team offer tailored support at every stage of the journey. “We create elevated, memorable trips that feel effortless,” she says. “Whether you need help choosing the right destination, want full-service itinerary planning, or simply need a trusted expert to handle your hotel bookings, The Weekend Discovery meets you where you are.”

What excites you most about the future of your industry? Travel is becoming more intentional. People aren’t waiting for the “one big trip” anymore—they’re embracing long weekends, milestone celebrations, school breaks, and time away just because. At The Weekend Discovery, we believe incredible travel experiences don’t require three weeks off or endless hours of research. What excites us is helping clients make the most of their time—so every trip feels effortless and full of meaning.

What’s a trend you’re embracing—or challenging? We fully embrace the rise of high-touch planning, even for shorter trips. That’s exactly what we offer—seamless support from start to finish, whether it’s five nights in London or just a long weekend in Napa. For our clients, luxury is about access, personalization, and not having to think about a single detail. One client said it best: “The most luxurious part was not having to make a decision.” That’s the experience we aim to deliver.

How do you define confidence—and how have you built it? Confidence is knowing your value and being clear on what you offer. At The Weekend Discovery, we know that travel is an investment—not just financially, but in time, which is often your most valuable resource. When clients tell us it was the best trip they’ve ever taken, or that they felt fully supported from start to finish, we know we’re doing the work we were meant to do—creating meaningful travel moments that become part of their story.

What legacy do you hope to leave behind? That I helped clients take the trips they didn’t think were possible. And personally, I hope my daughters see that it’s possible to build something that reflects your strengths and interests—and to carry a global mindset wherever you go.

For more information, visit theweekenddiscovery.com.