Tucked between long island's north and south forks, shelter island feels like a world of its own. days here unfold at an easy pace, with mornings at the market, afternoons spent swimming and exploring by bike and evenings gathered by the water. accessible only by ferry, the island has long been a beloved summer escape for families. from favorite places to eat and stay to beaches, nature trails and a boat ride to sag harbor, discover our guide to summer on shelter island.
TO STAY
The Pridwin Hotel & Cottages
a shelter island classic overlooking crescent beach, the pridwin is ideal for family summer vacations. spend the day by the pool or on the beach, explore the island by bike and gather for dinner overlooking the water.
summer mondays at the pridwin
make the most of your family getaway with an extra day on shelter island. guests staying sunday night will receive a complimentary 50-minute boat cruise on monday, a bottle of rosé, and a special gift from minnow. available through september 2026, subject to availability.
COFFEE AND BREAKFAST
marie eiffel market
start the morning with coffee, fresh pastries and breakfast by the water. stop back before the beach for sandwiches and picnic provisions to take along for the day.
TO EAT
opties and dinghies
a casual island favorite for dumplings, noodles and sweet treats. an easy stop for lunch with the family.
the 1901 grill
a relaxed spot for a casual family meal in the heart of the island.
salt waterfront bar & grill
head to the water for seafood and summer favorites in a laid-back setting. arrive by boat if you can.
TO SEE AND PLAY
wade's beach
a favorite for families, with calm water and plenty of room for a long day by the bay.
mashomack preserve
explore miles of trails through one of the island's most beautiful natural landscapes. choose a shorter walk for little ones or spend the morning exploring as a family.
sylvester manor educational farm
visit the historic farm, explore the grounds and stop by the seasonal farmstand for locally grown produce.
whale's tale
an old-fashioned summer stop for mini golf and ice cream with the kids.
take a boat to sag harbor
make a day of it and cross the water to sag harbor for lunch, shopping and a walk through town before heading back to the island.
TO SHOP
marie eiffel market
beyond breakfast and coffee, the market is a favorite stop for gourmet provisions and everything you need for an afternoon picnic.
shelter island heights
wander through the historic neighborhood near the north ferry and pop into the island's small shops for local finds.
sylvester manor farmstand
pick up seasonal produce and locally made goods to bring back to your summer table.
SITTER NIGHT
vine street café
book a table for a special dinner and enjoy one of the island's most beloved restaurants.
sunset at crescent beach
end the day by the water and watch the sun set over the peconic bay.
the pridwin hotel & cottages
stay close to home with dinner and drinks overlooking the water.
sag harbor by boat
head across the water for dinner in sag harbor, then return to shelter island under the stars.
Insider Tips
choose your ferry
there are two ways to reach shelter island by car ferry. take the north ferry from greenport if you're coming through the north fork or the south ferry from north haven if you're arriving via the hamptons and sag harbor.
plan ahead for the beach
seasonal parking permits are required at town beaches, so arrange yours before settling in for the day.
camp quinipet
for families staying a little longer, camp quinipet offers summer programs for children in a beautiful waterfront setting. a beloved shelter island tradition, it's a wonderful way for little ones to spend their days outdoors, make new friends and experience classic summer camp life.
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