Day: Playland Park Beach; Rye, NY (45mins from NYC by Metro-North) Rye’s preppy year-round residents spend most sunny days at private clubs, but the public beach attracts a more down-to-earth crowd. The coast is just steps away from the Playland amusement park (day pass $30), the public pool (day pass $6, park-and-beach combo pass $8) and a charming boardwalk where parts of the movie Big were filmed (914-813-7010, ryeplayland.org). After sunning yourself—or luxuriating in the shade (umbrella and chair rentals $3 each)—grab a swordfish BLT sandwich ($15.95) and sangria ($8) at waterfront restaurant Seaside Johnnies (914-921-6104, seasidejohnnies.com). Day pass $4.
Weekend: Ocean Beach; Fire Island, NY (2hrs from NYC by car or train and ferry) Although venturing out to this car-free oasis can seem intimidating, the aah moment when you board the ferry makes the effort worthwhile. This town is one of the most happening locales on Fire Island, with a diverse crowd that includes local families and hard-partying millennials. If you fall into the latter crew, you’ll find your kindreds at late-night hot spots such as Island Mermaid (631-583-8088, islandmermaid.com). Where to stay: The centrally located Palms Hotel (631-583-8870, palmshotelfireisland.com) won’t necessarily be easy on your wallet, but your booking comes with perks, including bicycles, beach chairs, towels and umbrellas. There’s also a social courtyard where guests can nosh on free watermelon and fresh popcorn or grill their meals on the barbecue. Rates start at $149. Mention TONY to receive 10 percent off one night’s stay Mon–Thu, Sun in May and June.
Long weekend: Montauk, L.I. (3hrs from NYC by car, 4hrs from NYC by LIRR) Of all the Hamptons hamlets, Montauk is known for being one of the more mellow scenes. Grab a bite at Navy Beach (631-668-6868, navybeach.com), a casual shoreside eatery serving refined, Asian-inflected dishes such as seared scallops with curried cauliflower ($28). Where to stay: Use Ruschmeyer’s as your home base. The summer-camp-themed hotel—complete with a tepee, picnic tables and white lanterns—is a ten-minute drive or 25-minute walk to the picturesque Ditch Plains beach, where pro surfer Mikey DeTemple conducts surfing lessons ($120 per hour) for hotel guests. Postwaves, you can hang out at the Sand Bar beer garden ($6 for a brew), enter a Ping-Pong tournament or watch a movie on the Magic Lawn. (631-668-2877, kingandgrove.com). Rates start at $207 during off-season, $475 per night during peak season.