Each of Long Island [1]’s four sections—North Shore [2], North Fork [3], South Shore [4], and South Fork [5]—can easily be done in a day or two, depending on how many stops you make, or can be combined into one long loop that begins and ends in New York City [6].
If you do make the 120-mile trip from Manhattan [7] to either the busy South Fork or the quieter North Fork, you’ll want to overnight there at least two nights.
A five-day trip would give you time to explore both forks and make stops at the North Shore’s Oyster Bay [8] and Cold Spring Harbor [9] on the way back.
Good day trips from Manhattan include Oyster Bay and Cold Spring Harbor, as well as Jones Beach [10], Fire Island [11], and Port Jefferson [12].
Links:
[1] http://www.moon.com/destinations/new-york-city-long-island/long-island
[2] http://www.moon.com/destinations/new-york-city-long-island/long-island/the-north-shore
[3] http://www.moon.com/destinations/new-york-city-long-island/long-island/the-north-fork
[4] http://www.moon.com/destinations/new-york-city-long-island/long-island/the-south-shore
[5] http://www.moon.com/destinations/new-york-city-long-island/long-island/the-hamptons
[6] http://www.moon.com/destinations/new-york-city-long-island/discover-new-york-city
[7] http://www.moon.com/destinations/new-york-city-long-island/manhattan
[8] http://www.moon.com/destinations/new-york-city-long-island/long-island/the-north-shore/oyster-bay
[9] http://www.moon.com/destinations/new-york-city-long-island/long-island/the-north-shore/cold-spring-harbor
[10] http://www.moon.com/destinations/new-york-city-long-island/long-island/the-south-shore/jones-beach
[11] http://www.moon.com/destinations/new-york-city-long-island/long-island/the-south-shore/fire-island
[12] http://www.moon.com/destinations/new-york-city-long-island/long-island/the-north-shore/port-jefferson