This page is organized in order of West to East. “How to Get There” directions are assuming you're coming from Manhattan.

Long Beach

Google Maps. Long Beach is a city located on a barrier island just off south of Long Island. Long beach is known for its decent bar/restaurant scene, easy train access and good surfing. In fact, the 2011 Quicksilver Pro contest was held in Long Beach. The waves aren't huge but they're a good shape and fairly consistent because of the way nearby currents work.

Getting There & Back

Long Island Railroad trains run from Penn Station to Long Beach station roughly every 20 minutes during weekend mornings. A PDF schedule can be found here or you can use the LIRR's interactive planner here. Note that some trains may require you to switch at Jamaica or Lynbrook. There are trains at 12:28am and 3:53am for late night return trips, so some careful planning is required if you don't want to miss the 12:28am. If you are in a pinch you can take a taxi to Rockville Centre, which is on the Babylon line, and catch a 1:32am or 1:59am train.

The train station is in the heart of Long Beach and is only blocks from the boardwalk & beach. There is no major need for cabs except perhaps to cross the bridge for dinner in Island Park.

Notable Restaurants and Bars

  • Jordan's Lobster Farms - Just over the bridge to the North in Island Park is Jordan's Lobster Farms. They have an outdoor window where you can order lobster and other seafood at reasonable prices. Expect a long line that moves fairly quickly. There is an outdoor picnic table area overlooking the canal where you can sit down with your food. There is also some indoor seating but I've never used it. Also notable: you can go inside and see the tanks where they actually store the live lobsters. I assume they do some sort of wholesale business as the tanks are much larger than what you'd see at a supermarket/restaurant.
  • Pop's Seafood Shack - Also in Island Park, Pops is one of my favorite places. They have a full sit-down restaurant serving [overpriced] seafood and general American dishes, but expect wait times of 1.5-2 hours if you arrive after 5:30pm. The real draw, however is the artificial beach and bars peppered around the property. The beach has Adirondack chairs for lounging and a few firepits you can vulture up when another group leaves. Live entertainment or DJs are common on weekends. The crowd transforms over the course of the night from family friendly until around 7pm to more adult/chill until 10pm and then more intense afterward.

Ocean Beach, Fire Island

(Google Maps). Fire Island is the easternmost barrier island on Long Island's south shore. Ocean Beach is my favorite area of Fire Island if I want restaurants and bars along with the beach. The experience of taking the ferry to the island makes you feel like you're really going someplace special. When you arrive there are narrow streets with no cars and lots of really quaint vacation bungalows set in wooded lanes. The town is small but nice.

Be prepared to spend an extra premium on drinks and food though, as all supplies need to arrive by ferry and the owners make sure to price that in. A cheaper option might be the local grocery store (near the ferry dock) but that's pricier than your local supermarket too. Perhaps pack a picnic lunch? The beach is crowded but nice and is a short walk from the docks. Also note that a water taxi is available for visiting other parts of fire island (like Sunken Forest).

Getting There & Back

Trains leave Penn Station on the Montauk branch for Bay Shore roughly every 30 minutes on weekend mornings (PDF schedule). The ferry from Bay Shore runs at least every hour throughout the morning but check the schedule. Once at the station you can either walk to ferry (directions, 0.9 miles/18 minutes) or take a cab. There should be a lineup of taxis and/or a shuttle bus at the station or you can call Tommy's Taxi Service at (631) 665-4800. Or just make sure you invite your Long Island friend who has a car with you 8-).

The last ferry back is at 1:00am, however the last two LIRR trains are at 10:47pm and 12:55am. After that you're hiring a car or waiting hours for the first morning train.