Shelter Island is located between Greenport and Sag Harbor on the east end of Long Island. It is definitely a hidden gem and a perfect summer vacation spot. Many people decide to make it their year-round home. In the first place, you’ll discover a wonderful mix of natural beauty, gorgeous beaches and beautiful wildlife. 
Secondly, there are many delicious restaurants, a few hotspots and lots of fun. Let’s not forget sports. Shelter is a boaters paradise and a golfers haven. In addition kayaking, stand up paddle boarding and other water sports are available. 
Furthermore one of the best ways to explore the island is by bicycle. Many hotels offer complimentary bicycles. Therefore you can get some exercise before hitting the beach. There is something to do for everyone on Shelter Island. Let’s start exploring……
Getting to Shelter Island
. The only way to reach Shelter Island is by ferry or boat. There are two ferry stations on Shelter: the North (Greenport) and the South (Sag Harbor). My favorite way to get here is from Greenport via the LIE and Sound Avenue. It is a pleasure to pass all the beautiful wineries and lively farm stands. The ferry ride is about 5 minutes. Alternatively, you can also take Sunrise Highway into Sag Harbor and then ferry (three minutes) to Shelter Island.
North Ferry Prices:
One way vehicle + driver $11. Same day roundtrip $16. Passengers in vehicles or on foot $2
South Ferry Prices:
One way vehicles $14. Same day roundtrip $17. Passengers in vehicles or on foot $1
Shelter Island Sights
Stars Cafe – a great little breakfast place
BEACHES
Crescent Beach
My favorite beach is Crescent Beach. You will find a beautiful view, calm water and many yachts and sailboats. Not only can you play volley ball on the sand and indulge in various water sports, but there is a huge tent for massages on the beach. In addition, you can cross the road and have lunch or a drink at Sunset Beach Restaurant.
Silver Beach, Shell Beach, Wades Beach, Upper Beach and Lower Beach are beautiful and quiet. These are typically in residential neighborhoods and used by the residents.
Sleep – Shelter Island Hotels and Guesthouses
There are a handful of great hotels and guesthouses here, so book early – especially on July 4th or Labor Day weekends. Read on for some of my favorite picks.
Sunset Beach Hotel
Escape to Sunset Beach and you’ll feel like you’re waking up in a different world. Feel a European vibe in this unique, charming hotel located on Crescent Beach. Large studio rooms all have spacious sundecks facing the bay. Enjoy complimentary beach chairs with towels, bicycles and paddleboards. Play petanque and pingpong.
Sunset Beach’s restaurant
Sunset Beach has a terrific outdoor lounge area with a fire pit and occasional live music. The three-level restaurant and bar area are always filled with a lively crowd. Rosé wine is flowing and a Frosé is perfect on a hot summer day. Of course, DJ music plays from the afternoon into the wee hours of the night. Being right on the beach makes this the ultimate spot with a French twist.
The Pridwin Hotel
The Pridwin reminds me of a grand hotel. It has a huge lobby, very nice rooms and a pool. In addition, the upstairs balcony has one of the best dining views on the island, and great food. It is a 5 min walk to Sunset Beach, which is a hot spot both day and night.
Shelter Island House 
You will discover casual sophistication and a chance to explore the local feel without sacrificing luxury. The property has a pool and is close to Crescent Beach. The property opened a delicious new restaurant, Caci.
West Neck Guest House
West Neck Guesthouse, is only about two years old. The property offers comfy and beautifully appointed guest rooms all with king beds, private baths, flat screen TV’s with cable, and Wi-Fi. Just a 10 minute walk from Crescent Beach.
For EATS go to: Shelter Island Restaurants