Overnighter
Where you’re staying: On the tip of Shelter Island, Kona Kai Resort & Marina has just undergone a $22 million makeover, with more changes to come. The rooms are bright, colorful, and island-themed, and the pool area is sizeable, with a tiki bar in the works. The private beach has fire pits and guests can grab a s’mores package for dessert under the stars.
What you’re doing: At the Kona Kai Marina, rent kayaks, SUP boards, or Jet Skis. Afterwards, return to your room and freshen up for an early cocktail—happy hour happens every night. The property hosts live music acts in the lounge or on the beach, Wednesdays (BBQ & Blues), Fridays, Saturdays, and Sundays on Jazz Night. Sunday brunch at Kona’s waterfront restaurant, Vessel, also features live music plus a bottomless Bloody Mary bar with 66 different fixings. Rooms start at $129. resortkonakai.com
