Montauk, New York
A sunset sail at Montauk Yacht Club Resort & Marina

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.

Admiral Beach Bungalow Rooms at the Montauk Yacht Club have private patios that lead to the lakefront beach.
Admiral Beach Bungalow Rooms at the Montauk Yacht Club have private patios that lead to the lakefront beach.

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