SIGC | The Roundtree Amagansett

“There were four things that I thought were really important. The first one was to be humble and confident. Number two, be open-minded, but have a point of view. The third point was to know there is no substitute to working hard. Last but not least was to embrace change and challenges.”

We’re in great company with Sylvia Wong, the Owner of The Roundtree Amagansett, where she meticulously polished a hidden gem into an award-winning luxury boutique hotel in the heart of the Hamptons that pays homage to Amagansett’s historic farmsteading legacy while embodying the spirit of this iconic east coast destination.

Her journey from corporate law executive to passionate first-time hotelier exemplifies a dream transformation—inspired by her global travels to create a rarefied Hampton's experience where guests can truly live like locals.

In this episode, Sylvia shares her inspiring career pivot, the challenges of opening during a pandemic, and how she crafted an authentic home-away-from-home experience that keeps guests returning season after season.

Top Takeaways

[1:40] How Sylvia's corporate career took her to hidden corners of the world where she embraced diverse cultural expressions through architecture and design and found a motherly instinct for nurturing guest experiences.

[5:05] It all began with a single raised hand in a meeting, a serendipitous stop on the Jitney shuttle, and Sylvia's unwavering determination to master the art of hospitality—despite having no industry experience whatsoever.

[9:30] Steps from Main Street, Sylvia discovered an unassuming property with centuries of stories hidden beneath its weathered shingles and expansive grounds.

[17:20] At The Roundtree Amagansett, luxury whispers rather than shouts—as guests discover thoughtful complimentary amenities designed to create moments of surprise and delight from sunrise to starlight.

[30:40] Why Sylvia’s sense of fulfillment is not found through financial means—it is in seeing genuine happiness wash over her guests' faces as they share their stories and experiences.

[34:40] There is much creativity and collaboration yet to come—from new culinary offerings to seamless wellness incorporations to thoughtfully designed spaces where families and friends can gather to create their own Hampton traditions for generations to come.