Shelter Island Summer Vacation Guide

Stipulated: the perfect travel time for a three-day weekend getaway is four hours. More, and you waste your vacation. Less, and you’re still near home. Hence our series: The 4hr. Rule, dedicated to revealing the best destinations that are far away, yet still close to home.

There are two types of people in New York: those who love the Hamptons, and those who say, “F*** that traffic; I’m not going to the Hamptons.”

But what if we told you that the Hamps hop, skip and a jump … is now just a hop?

Responsible for this development: a handsome new seaplane service ready to sweep you and seven friends away to ever-charming Shelter Island, an escape-the-swelter oasis brimming with private beaches, bike rides, barbecues and way, way fewer people than you’ll find in Montauk.

Come Sunday evening, you’ll be flying peacefully back home — while smirking at the gridlock a few thousand feet below.

Here’s the plan.

GET THERE: Through September 12th, StndAir’s eight-passenger seaplane is soaring to-and-from East Hampton and Shelter Island. Should you fear small planes, they’ll help take the edge off: each 45-minute flight comes with André Balazs rosé, in-flight sweets from Narcissa pastry chef Deborah Racicot and complimentary beach goods like Soleil Toujours sunscreen. And if Saturday and Sunday isn’t enough R’n’R, they’re inviting you to play hooky. The Sunset Hooky package is for the Friday afternoon escape artist. Upon arrival, those who broke free will be welcomed with a three-course lunch on Sunset Beach and spend the rest of the afternoon sipping cocktails on the patio, starting a petanque tourney or doing whatever the hell you please.

STAY: Shelter Island may only be 27 square miles, but we have options. There’s the stately, revamped and very beautiful Shelter Island House; the family-friendly Dering Harbor Inn; the stylish Sunset Beach, serene but stocked with the city’s glitterati (be wary of fully-booked weekends); and our favorite, The Chequit. This 37-room refuge was a 1940s high-society go-to for Marilyn Monroe and Frank Sinatra. And it’s easy to see why. The vibes are rustic meets Wes Anderson kitsch, but luxurious and comfortable in practice. There’s a six-room cottage available for larger groups. And if you’re coming with a whole crew, the island is also swarmed with lovely rentals.

EAT: Here is exactly what you want to chow down on before you depart: Vine Street’s fresh cut potato chips, wine (all of it) and spaghetti bolognese; Sunset Beach Hotel’s burrata with truffles, rosé and moules marinières; Bob’s Fish Market’s daily special; and 18 Bay’s four-course Italian tasting menu. For chilling out, head to Salt for blackened fish tacos and cruise next door to Shipwreck Bar after for live music and local wine. You’ll find the best coffee at Stars Cafe and the best floats and shakes in the area at Whale’s Tale.

DO: Biking around is the best — and if you’re coming by plane, only — way to get around. Piccozzi’s Bike Shop has you covered. You’ll be taking that cruiser over to Shell Beach for lollygagging among wildflowers and swimming in warm waters. Then pedal on to the Mashomack Nature Preserve for a coastline hike or to Shelter Island Kayak Tours to take to the open waters and see the island from a different perspective. Pack a picnic and you can paddle up for a rest and a bite at historic Taylor’s Island. Pro tip: if you’re on-site during the week, don’t miss Pridwin’s beachside barbeque on Wednesday evenings.