About Us

Our story

The Weekend Discovery was founded in 2023 with a simple belief: meaningful travel doesn’t require unlimited time, it requires the right plan and the right partners.

As a meticulous planner by nature and a working mom by reality, founder Jackie Flaherty understood how easily travel can slip to the bottom of the list. Long vacations are not always realistic, and even when the time exists, the logistics can feel like a second job. Jackie built The Weekend Discovery to make elevated travel feel doable, efficient, and genuinely enjoyable.

What started as a love for uncovering exceptional hotels quickly became the foundation of the business. Jackie plans trips around properties that deliver, because the right hotel changes everything: how you land, how you sleep, how you reset, and how the trip feels as a whole. Today, The Weekend Discovery pairs thoughtful itinerary design with hotel expertise and strong industry relationships, helping clients access preferred partner perks, priority communication, and more thoughtful stays at many 4- and 5-star properties.

The Weekend Discovery is also built for real life. We help busy families and couples actually take the trip and do it right, with custom guidance that answers the questions that matter most: where to go, when to go, what it will cost, and what’s worth your time once you arrive.

From quick weekend escapes to multi-stop journeys, every booking is shaped by timing, access, and intention, so it feels seamless in execution and rich in meaningful travel moments.