Gurney's Montauk pool deck
The only true on-the-sand resort in the Hamptons, with a pool deck that runs loud all season.
Peak: Saturday 1-5pm
People-Watching, Honest Edition
Where the East End’s people-watching actually happens. Models, scouts, celebrities, the trade press, the social set. We don’t sell access; we point you at the door. Some of these are quiet luxury, some are loud Friday-night chaos. Both have their place.
If you’re here because you want to see hot people: pool day at Gurney’s, Saturday lunch at Sant Ambroeus, Sunday polo at Two Trees Farm. That’s the canonical order. Everything else is supporting material.
7 spots
Pool day
4 spots
Montauk · 4
The only true on-the-sand resort in the Hamptons, with a pool deck that runs loud all season.
Peak: Saturday 1-5pm
Tiny rooms, a tiny pool, and a concert deck on Fort Pond that functions as the single loudest summer venue…
Peak: Friday sunset through Sunday 2am
A former fish dock converted into a sunset picnic deck with lobster rolls and a rosé list longer than the…
Peak: Saturday 4-7pm
Sunset hour
7 spots
Montauk · 5
The only true on-the-sand resort in the Hamptons, with a pool deck that runs loud all season.
Peak: Saturday 1-5pm
Tiny rooms, a tiny pool, and a concert deck on Fort Pond that functions as the single loudest summer venue…
Peak: Friday sunset through Sunday 2am
A former fish dock converted into a sunset picnic deck with lobster rolls and a rosé list longer than the…
Peak: Saturday 4-7pm
Montauk · 5
A small inn above Lake Montauk with the best sunset view of any restaurant in town and a kitchen that…
Peak: Friday and Saturday 6-8pm
Sag Harbor · 2
The second-floor deck over Sag Harbor Cove is the best-priced sunset view on the South Fork — bar snacks and…
Peak: Friday and Saturday 6-8pm
The 1960s motor inn that was Baron's Cove sold, renovated, and reopened summer 2026 as Faraway Sag Harbor.
Peak: Friday and Saturday 6-9pm
Saturday night dinner
3 spots
Montauk · 1
A small inn above Lake Montauk with the best sunset view of any restaurant in town and a kitchen that…
Peak: Friday and Saturday 6-8pm
Sag Harbor · 2
The second-floor deck over Sag Harbor Cove is the best-priced sunset view on the South Fork — bar snacks and…
Peak: Friday and Saturday 6-8pm
The 1960s motor inn that was Baron's Cove sold, renovated, and reopened summer 2026 as Faraway Sag Harbor.
Peak: Friday and Saturday 6-9pm
After dark
1 spot
Montauk · 1
Tiny rooms, a tiny pool, and a concert deck on Fort Pond that functions as the single loudest summer venue…
Peak: Friday sunset through Sunday 2am
1 spot
Pool day
1 spot
Shelter Island · 1
André Balazs's St-Tropez-in-the-Peconic.
Peak: Saturday 4-8pm
Sunset hour
1 spot
Shelter Island · 1
André Balazs's St-Tropez-in-the-Peconic.
Peak: Saturday 4-8pm
Saturday night dinner
1 spot
Shelter Island · 1
André Balazs's St-Tropez-in-the-Peconic.
Peak: Saturday 4-8pm
Hampton Classic week
A full social week, not a day trip — social calendar for the week’s schedule.
Galas & benefits
The Watermill Center benefit, Parrish Midsummer, Guild Hall Summer Gala, and Authors Night are the four black-tie nights that draw the city social set out east. Tickets are public. The full schedule lives on the galas page, cross-linked to the social calendar.