If you're planning a two-day adventure, here's what we’d recommend to make the most of your time on Shelter Island. And as you explore the island, don’t forget to bring along our free 32-page guide to the little-known historical places of Shelter Island with directions to each of those remarkable sites. You’ll likely be passing by all of them while you’re here.

Day 1: Nature and Nostalgia

Start your day with a dose of history at the Shelter Island Historical Society. Housed in the 1743 Havens House, it provides fascinating insights into the island's past through artifacts, photographs, and documents. If you happen to visit during one of their events, you're in for a treat. Visit their website for hours and upcoming events.

From quaint boutiques and artisanal crafts shops to unique antique stores and fresh farmer's markets, Shelter Island offers a shopping experience as diverse and charming as the island itself. Browse our directory for an easy way to find what you’re looking for.

Head next to the Sylvester Manor Educational Farm for a trip back in time. The Manor house, dating back to 1652, boasts lush grounds, historic charm, and a working organic farm. Be sure to explore the Manor house, and, if you're lucky, catch one of their many events or workshops.

After a day full of exploration, unwind at one of our island beaches (see pictures of the beaches on our Shelter Island Beaches page). This sandy haven is perfect for a relaxing swim and sunbathing in the summer, or, no matter what the season, simply soaking in the views of the surrounding island waters. Sunsets here are a sight to behold.

Day 2: History and Leisure

Kickstart your day at the "Jewel of the Peconic," Mashomack Preserve. This 2,350-acre nature preserve is the perfect place to soak up some fresh air and stretch your legs. Choose from four different trails, each offering unique glimpses into the preserve's diverse habitats—20 miles of trails total. Don't forget to check out the visitor's center with exhibits and interpretive programs, as well as restrooms and parking.

Spend your afternoon at the serene Shell Beach, a hidden spot known for its shells and peaceful atmosphere. Pack a picnic, launch a kayak, or scour the beach for marine life.

Shelter Island is home to a variety of restaurants serving delicious local and international cuisine. There’s a restaurant for all tastes and budgets. You can view our Shelter Island restaurant directory here.

This itinerary gives you only a glimpse of what the island has to offer, but we think it’s a fantastic start.

We hope you enjoy your visit!