Manhattan to Water Mill

The grist mill, the pond, the discreet estates.

Hampton Jitney

2h 45m - 4h 30m

$43 prepaid online / $51 pay on board, each way; Ambassador class $68 / $78 (select seating +$9)

Direct from East Side Manhattan stops. Friday afternoons can add 90+ minutes of Route 27 traffic. Book ahead in season.

LIRR Cannonball (Fri only, in season)

~2h 30m

$30-$50 standard reserved; Parlor Car ~$70-$90

All-reserved Friday express. Parlor Car has table service. Stops at Westhampton, Southampton, Bridgehampton, East Hampton, Amagansett, Montauk.

LIRR regular (off-peak)

~3h + transfer

$20-$30 off-peak

Year-round but slow and usually requires a transfer at Jamaica or Babylon. Cheap.

Blade helicopter

~40 min

2026 season, May 21-Sep 8: Southampton Pass is a fixed $595/seat to Southampton only; the Summer Pass costs $3,375 and then buys $795 seats to any of the five destinations for the rest of the season, any day, booked as little as 20 minutes ahead. No walk-up single-flight fare is published — you buy a pass first.

30th St Heliport to East Hampton (HTO), Southampton, or Montauk. Confirm landing field at booking — HTO has noise restrictions.

Seaplane (Tailwind / similar)

~40 min

Charter quote only — no operator currently publishes a per-seat Manhattan-to-Hamptons fare

East 23rd St Skyports to East Hampton. Operators also serve Montauk and Southampton.

Drive yourself

2h - 5h

Gas + ~$15 tolls + parking

LIE to Sunrise Highway (NY-27). Friday afternoon eastbound and Sunday afternoon westbound are brutal. The Shinnecock Canal bottleneck is unavoidable.

A note on timing

Friday 2pm-8pm eastbound and Sunday 1pm-7pm westbound are the bad windows on Route 27. If your plan involves a car or a Jitney during those hours, double whatever the map says.