Sylvia Wong spent decades as a corporate law executive, ultimately serving as General Counsel of IBM's Global Growth Markets. Then she walked away and opened a boutique hotel on the East End of Long Island in the middle of a global pandemic, with no background in hospitality and no reservations on opening night.
The Roundtree sits on two acres of land in Amagansett that has been settled since the 1600s — one of the hamlet's original founding family properties, now transformed into fifteen rooms and five standalone cottages, one of which is over 250 years old. Sylvia brought the same rigor she applied to global operations to every detail here: commissioned artwork throughout, Frette linens, Matouk towels, and a guest experience that feels like someone's extraordinarily well-curated home. This is the quieter side of the Hamptons — steps from Main Street, ten minutes from the beach, and a world away from the version of the East End that announces itself.
Amagansett's creative and agricultural community is deeply shaped by the women who farm, make, and build here year-round — long after the summer crowds have gone. Every experience on this retreat is an invitation into that community, on its own terms.
Images courtesy of Judy Pak Photography.
Day 1
Arrival and Welcome
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Welcome the group to The Roundtree, Amagansett. Guests settle into their luxurious rooms or private historic cottages.
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Gather on the lawn for the hotel’s complimentary afternoon tea.
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Located in Bridgehampton, the restaurant celebrates the remarkable bounty of the East End—local farms like Acabonac Farms and Balsam Farm and fresh catches from Montauk waters—prepared with the global perspective and meticulous care that define Chef Dewa's craft.
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Transition seamlessly to The Roundtree’s signature evening bonfire. Unwind around the fire pit with s'mores.
Day 2
Farm Tour, Stroll, & Private Matriark Salon
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Start the day with the hotel's complimentary signature continental breakfast.
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Walk right next door to Amber Waves Farm for a private garden tour and agricultural workshop hosted by co-founders Katie and Amanda.
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Take a leisurely walk through the historic town of Amagansett to visit shops and local vendors.
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Host a private Matriark Salon on the hotel property. Founder Patricia Assui Reed joins the group for an intimate gathering to connect, share stories, and discuss women's leadership and design.
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il Buco al Mare, features a simple, relaxed menu presenting the best local seafood & produce
Day 3
Sound Healing & Luxury Beach Afternoon
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Start the day with the hotel's complimentary signature continental breakfast.
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Wake up to a private Sound Healing / Find Your Balance session.
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After the coastal hike, head down to the Atlantic shoreline for The Roundtree's custom Beach Picnic experience.
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Rosie’s helps support Amagansett’s vital farming community while offering fresh, high-quality food we can all feel good about.
Day 4
Departure
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A final morning breakfast in the garden before a 11:00 AM checkout.
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Private transfer from the hotel
This retreat is for you if…
You are a female founder or entrepreneur.
You believe that women supporting women is not a slogan. It is the way you actually move through the world.
You want to travel somewhere that matters — where the experiences go deeper than the destination — into the lives of the women who shape it.
You understand that investing in yourself is not a luxury — it is the strategy.
What this is not:
A conference, mastermind, or workshop with a better view.
A large group where you are one of many.
A retreat where you are expected to pitch or perform.
A wellness trip in the traditional sense. What you'll find here goes further — restoration through experience, community, and the quiet power of giving back.
A girls' trip that happens to be in a beautiful location.
The details:
Location: The Roundtree, Amagansett, New York
Dates: September 2027 — exact dates confirmed upon application
Duration: 4 days · 3 nights
Cohort size: 7 women
Flights: not included — guidance provided upon application
This cohort is limited to 7 guests and curated for values alignment. If this retreat feels like yours, I’d love to hear from you.