Shelter Island Travel Guide

  • Shelter Island
    by sayville
  • Things to Do
    by sayville
  • Things to Do
    by sayville

Shelter Island Things to Do

  • sayville's Profile Photo

    by sayville Written Oct 4, 2002

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    We drove all over the island. It was one of those warm fall days. Had to be 70F. We stopped at several beaches as we drove around. At one of the stops we saw this rock with a painting of the American Flag. I must say it looked much better in person. I also took one with the sun setting, but it came out much to dark to see the flag.

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Shelter Island Hotels

  • Dering Harbor Inn

    13 Winthrop Road, Shelter Island, New York, 11965, United States

    Satisfaction: Excellent

    Good for: Families

  • The Pridwin Hotel

    81 Shore Road, Crescent Beach, Shelter Island, New York, 11964, United States

    Satisfaction: Average

    Good for: Solo

  • Ram's Head Inn

    108 Rams Island Dr, Shelter Island, New York, 11965, United States

    Satisfaction: Very Good

    Good for: Couples

  • Sunset Beach

    35 Shore Rd, New York, 11965, United States

    Satisfaction: Terrible

    Good for: Couples

  • Candlelite Inn

    Route 114 South, Shelter Island, New York, United States

    Satisfaction: Excellent

    Good for: Couples

Shelter Island Transportation

  • sayville's Profile Photo

    by sayville Written Oct 4, 2002

    2.5 out of 5 starsHelpfulness

    You must take a ferry from either the south shore or north shore of Long Island. The ferry ride is only a few minutes long. The ferry is small and only holds about 10 cars at one time, but they run often. No reservations are needed.
    We drove around the island. I guess if you were in shape, you could take a bicycle over and bike around the island.

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Shelter Island Local Customs

  • by thebany Written Oct 9, 2006

    2.5 out of 5 starsHelpfulness

    Sailing across the water on one of the ferries to Shelter Island is almost immediately reinvigorating. If you drive you absolutely must get out of your car during the ferry ride. Shelter Island is both a casual vacation spot as well as a laid back place to live, a place to eat right after leaving the beach still covered with sand. It is a family friendly/pet friendly environment. And don't forget your flip flops during the summer time.

    This can be seen best by an experience I had at the Vine Street Cafe located off of 114, aka South Ferry Road. This restaurant is awesome. Great food prepared and presented with care using all local and seasonal product, attentive service, and a well diversified wine list. I was sitting out front of the restaurant and watched a couple ride up on their bicycles. And yes, they were there for dinner. I also saw one guest bring their very well behaved dog to dinner. They of course sat outside with their sweet pooch tucked under their table while they enjoyed their dinner and wine.

    There are also many other things to do in and around Shelter Island. On the island there is a fantastic state preserve which is quite beautiful to explore both by car and on foot. Mashomak State Preserve is the name. And of course there is the beach, which if you're lucky you can claim one of the fun beach chairs that are provided. Rent a bicycle or kayak to explore both by land or sea. Look for Sunset Beach Hotel and Restaurant across the street to grab an early glass of wine before it packs out for the evening.

    On the North Fork of Long Island, a quick ferry ride away, there are many many different local wineries with tasting rooms that are open just about every day. You'll also see fresh vegetable farm stand after farm stand driving down the main road through the North Fork. If you go to the South Fork by way of the South Ferry, you'll find Sag Harbor with a lot of fun shops and good food. Just look around. You'll see what I'm talking about.

    Related to:
    • Water Sports
    • Wine Tasting
    • Family Travel

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