There are multiple beaches all over Shelter Island: Hay Beach, Wades Beach, Shell Beach (where Jake proposed), and Crescent Beach (aka Sunset Beach). Plenty of coastline to stroll, collect shells, and enjoy a refreshing dip.
A public 9-hole golf course on Shelter Island!
Enjoy hiking at Mashomack Preserve! Various trails of different lengths - check out the AllTrails app to find the right hike for you. Make sure to wear high socks and always check for ticks when you're home.
Rent bikes and tour the island - call ahead to ensure they have enough available!
Best seafood on Shelter Island if you're looking for a casual lunch or dinner spot.
Take the North Ferry for a quick ride over to Greenport! Leave your car on Shelter and travel by foot since everything is within walking distance. Great restaurants, bars, cute shops, the list goes on and on.