The best way to enjoy Montauk? On the deck of a sailboat, glass of champagne in hand, cruising around at sunset on a private charter of the Montauk Yacht Club Resort & Marina’s Sunset Sails program (from $220). Those looking to brush up on their sailing or swimming skills can take a lesson in either.
While You’re In Town: Montauk is known for its surf, so catch a wave with CoreysWave. Play a round of golf at Montauk Downs State Park, then cap off things with rum punch, fresh oysters and ocean views at Gosman’s Dock restaurant.
Where to Stay: Rooms at the Montauk Yacht Club Resort & Marina are preppy and bright—opt for the Admiral Beach Bungalow Room, which has private beachfront patios. End the day with the nightly bonfire and s’mores, or a nightcap at B-Bar. From $249 per night