Montauk is a relaxing and enjoyable destination.  Stay at a motel right in town.  Let this vacation be like a spa treatment. Let it be relaxing, and take your time. It's not the type of place that has too much going on.  You have to take a walk around the town, and if you have kids don't forget to take them to the store "A little bit of everything."  They will love it. The store has lots of fun little gadgets and sand toys. During the day, it's nice to just spend the day on the beach, and then if you are looking to take a little break would go to Nick's, a restaurant / bar right on the beach. They have music and food.  Or drive about a minute down the road and have lunch at "Topside" and watch the boats go by. Some good restaurants around the area are: The Harvest (which is great for family style dining). Also try Gosman's Dock.  On weekends they have live bands there and there is alittle bit of shopping. Great place to watch the sunset! At night  everyone has fires on the beach. Make sure to secure a good spot around 7:30 or 8:00pm. or just join someone else's fire. Good way to meet people and have a good time. Also, if you have kids, or just a sweet tooth, there's a quaint candy shop in town.