long island trips

You can definitely do it. FH and I have been taking tons of daytrips to Connecticut and the Poconos lately looking for wedding venues, and they're 3 hours away or so. Depends on how much you like each other and how much time together in the car you can stand!

I just Mapquest-ed it for you, and Montauk is exactly 100 miles from Valley Stream. With the usual LI traffic, going an average of 40 MPH on the highway (I'm being realistic!) that's 2 and a half hours there, a little less back if you come back later at night when the roads are more open.

I grew up in Oceanside and I've done day trips to Montauk. I like to leave early on Sat morning (by 10), it takes about 1 1/2.

There are some vineyards on the way too