Shelter Island offers a variety of activities that capture its natural beauty and relaxed atmosphere. One of the best things to do is to explore its pristine beaches, such as Crescent Beach, where you can enjoy sunbathing, swimming, or a leisurely walk along the shore. For nature enthusiasts, Mashomack Preserve is a must-visit; this expansive nature preserve offers numerous hiking trails where you can experience the island's diverse ecosystems and spot local wildlife.

Another enjoyable activity is to visit Shelter Island's historic sites. The Sylvester Manor Educational Farm provides a glimpse into the island's colonial past and offers tours of its historic house and farm grounds. Kayaking or paddleboarding around Shelter Island’s coves and inlets is also a popular way to appreciate its beautiful waterfront scenery from the water.

For those interested in local culture, checking out the Shelter Island History Center can be rewarding. Here, you can learn more about the island's heritage through its exhibits and archives. Additionally, Shelter Island has a number of charming local shops and dining establishments where you can indulge in fresh seafood and other regional cuisine.

Lastly, don't miss the chance to enjoy a relaxing sunset picnic at one of the island’s scenic viewpoints, such as Sunset Beach, where you can unwind and take in the serene evening views.