Although most people know of Montauk, it somehow still remains one of New York's best-kept secrets. Tucked away at the very tip of Long Island, a full three hours from New York City, it is a land all its own, with beautiful beaches, breathtaking sunsets, and a vacation vibe like no other place. While many folks settle for the familiar comfort of the Hamptons—at only half the distance from NYC—Montauk is well worth the trip for anyone seeking a true Vacationland environment. Sperry Top-Sider, the maker of the world's first boat shoe and the official footwear of vacations everywhere, would like to recommend a few fun activities and beautiful attractions that await you when you arrive.


If you're looking to soak up a little local color, the Montauk Point Lighthouse Museum has great exhibits regarding the region throughout the ages, including documents signed by George Washington and Thomas Jefferson. But even if you have no interest in spending your Vacationland time digesting a history lesson, the Lighthouse itself offers spectacular views of the surrounding landscape and ocean waters that are well worth checking out—provided you don't mind trekking the 137 steps up to the top.


On the western border of Montauk lies Hither Hills State Park, which not only has miles upon miles of rolling beach landscape, but also has the region's only public campgrounds, in case you feel compelled to make a night (or a few nights) of it. It's the perfect location to picnic, swim, and soak up the sun during daylight hours, then bunk down for a little bonfire-side R & R once the evening hits. For those who don't like to go too rugged, fear not, there are public showers available on site.


If you’re down to get wet, our surfing recommendation is Ditch Plains Beach. It's not only the most well regarded surf spot in Montauk, but on Long Island as a whole, attracting surfers from up and down the east coast. Lifeguards are on duty from 10am - 5pm in-season, and the beach has public showers available for when you're done riding waves for the day.


If you’re down to go even deeper, Montauk has a number of dive spots that offer a great scuba experience. However, some dive locales can be slightly treacherous to reach (Culloden Point) or crowded with other activities (Montauk Harbor West Side Jetty), so we recommend the Montauk Harbor East Side Jetty. It's an easily accessible dive site that you can reach by walking in from the beach, and you can expect to see a variety of fish—particularly when the water is warmer—as well as lobster during your dive. Just make sure to watch out for those lobster traps, and to take off your Sperry Top-Siders before you jump in.


Once you’ve dried off, there is no better way to end your day—and enjoy your Montauk Vacationland experience as a whole—than by taking a cruise out on the water. Several different boat lines offer daily sunset cruises to a variety of picturesque locations (the lighthouse, Fort Pond Bay, and others), all of which promise to deliver the ultimate relaxation that is our entire reason for going on vacation to begin with.

For more on Sperry Top-Siders spring collection and to start your Vacationland journey, click here.