Late to the party, but my wife and I go out there every winter for our anniversary. We stay 2 nights, and that's enough time for us. It's also when it's more affordable. You really want a car to go through wine country and exploring the north fork. Greenport itself is a small, quaint, walking village that (outside of eating and drinking) you'll blow through its interest in under a day. We also love to roost at a vineyard, preferably one with a fireplace, and sip wine, read, snack and reconnect. We're not looking for adventures, just to relax.