The classic Hamptons day sail. Leave Long Wharf on a building SW, carry the breeze through Noyac Bay, thread the North Ferry channel, duck into Coecles for a lunch anchor, then run the Mashomack shore back through Shelter Island Sound. Four legs, four different points of sail — this is the one you plan the whole summer around.
- Duration
- 4-6 hours
- Skill
- Intermediate skills
- Best wind
- SW / W
- Season
- summer, early fall
Protected-water sail that works for families and first-timers. Head out Three Mile on the outbound tide, reach across Gardiners Bay to Cedar Point Lighthouse, drop an anchor on the sand bar, lunch ashore at the county park, then run home on the returning breeze. Easiest big-water day on the South Fork.
- Duration
- 3-4 hours
- Skill
- Beginner-friendly
- Best wind
- SW / S
- Season
- summer
Exposed-water passage around the most dramatic coastline on Long Island. Exit the Lake on slack water, run the north shore under the cliffs, round Montauk Point under the lighthouse, then tack home with the afternoon SW in your teeth. Not a beginner day — the rip off the Point stacks up fast and the cell bars disappear a mile off the beach.
- Duration
- 5-7 hours
- Skill
- Advanced / exposed water
- Best wind
- W / SW
- Season
- summer, early fall
No cell signal on this route — download NOAA charts before you cast off.
Popular weekend passage across the Peconics. A building SW reaches you the whole way, Shelter Island opens on your starboard beam, and Greenport's transient dock puts you a block from oysters and a beer. Tie up, spend the night, ferry back — or run it as a round trip if the wind is polite.
- Duration
- half day
- Skill
- Intermediate skills
- Best wind
- SW / S
- Season
- summer, early fall
Lunch-hook trip to the edge of the most storied private island in the Atlantic. Anchor in 15 feet off the east shore, watch the ospreys work the cliffs, stay in the boat — Gardiners is private, no landing, no exceptions. Bring charts: cell signal drops to nothing once you clear the Napeague breakwater.
- Duration
- 4-5 hours
- Skill
- Intermediate skills
- Best wind
- SW / S
- Season
- summer
No cell signal on this route — download NOAA charts before you cast off.
The most forgiving big-water sail east of the canal. Shinnecock Bay stays flat in a blow, the western end opens toward Cupsogue's barrier-beach sweep, and you can reach back to the canal in almost any wind. Good first-day-out-of-the-slip sail.
- Duration
- 3 hours
- Skill
- Beginner-friendly
- Best wind
- SW / S
- Season
- summer
Small-boat and paddle scale — Sunfish, cat, kayak, SUP. Mecox and Sag Pond are coastal ponds barely separated from the ocean by a dune, so the wind is honest and the fetch is short. Quiet, glassy, and exactly the right place to learn to read a shifting SW on a small boat.
- Duration
- 2 hours
- Skill
- Beginner-friendly
- Best wind
- SW / W
- Season
- late spring, summer, early fall
A short reach across the western Peconic to the lee of Robins Island — a Peconic Land Trust preserve with no public landing. Anchor off the west shore in flat water, swim off the stern, watch ospreys nest in the cliff-top pines. Cell signal here is spotty; load charts in New Suffolk before you cast off.
- Duration
- 3-4 hours
- Skill
- Beginner-friendly
- Best wind
- SW / S
- Season
- summer
No cell signal on this route — download NOAA charts before you cast off.
