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Best play to stay on the island?

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berkeley
posts: 15
Best play to stay on the island?

Looking for some guidance about choosing the best place to stay on Shelter Island. We're a family of four (kids are 8 and 12) who love the outdoors, swimming, bike riding, kayaking, hiking and just hanging out in beautiful places. We'll be spending a few weeks visiting family and friends in the Tri-state area (nice, but not relaxing) but have reserved 4 days just for us to enjoy Shelter Island. Choosing between Ram's Head Inn and Pridwin which I guess are on opposite sides of the island and have some different amenities. Also, considering a small cottage which seems to be located about a mile from the beach at Midway road.

All seem lovely but I wonder if anyone is familiar with these Inns or the geography of the island so as to recommend where to stay for a relaxing (yet active) vacation for our family?

Thank you in advance for any tips. I will post this on the NYC forum as well since it appears that Shelter Island forum not so active (accommodations posts are old).

New York City, New...
Destination Expert
for New York City
posts: 84,107
reviews: 2
1. Re: Best play to stay on the island?

I haven't stayed at either but have been to both for a meal or just a look see. Ram's Head Inn doesn't have a/c which would bother me. It's very very pretty but also very removed from the rest of the island. I had dinner there some time ago and the food was nothing special. It's very pretty and something like a step back in time (well the whole island is). The Pridwin sits on "sunset beach" and is near the music school and the Sunset Beach hotel, another popular place. Someone on the NYC forum just mentioned having gone to the Dering Harbor Inn and liked it very much. Don't know if that's a consideration. YOu might like to PM him about his stay.

tripadvisor.com/ShowTopic-g60763-i5-k2745119…

berkeley
posts: 15
2. Re: Best play to stay on the island?

Thank you, nywhiz, for your suggestion of Dering Inn. I checked out that post and, when I called there, it seemed like just the kind of place we would like. Offers a little more independence as the units have kitchenettes and grounds have BBQs etc. . . A short bike ride to Sunset Beach but that's what we're there to do so should be fun.

I really appreciate your mentioning it - will do a trip report after our stay.

New York City, New...
Destination Expert
for New York City
posts: 84,107
reviews: 2
3. Re: Best play to stay on the island?

Great! I noticed you asked about restaurants. The 2 I mentioned in that post, Sunset Beach and Vine St. Cafe are the most well known. Sunset Beach is pricey but really transporting. YOu think you're in the Caribbean. The Dory is a fun place for lunch. I've never been for dinner.

New York City, New...
Destination Expert
for New York City
posts: 84,107
reviews: 2
4. Re: Best play to stay on the island?

PS, if you like classical music and will be there on a Fri. night, you should go to the free concerts they have at the music school.

www.hamptons.com/detail.php?articleID=4525

berkeley
posts: 15
5. Re: Best play to stay on the island?

Thank you for all the great suggestions. Sounds like fun.

Stamford, Ct
posts: 615
reviews: 13
6. Re: Best play to stay on the island?

The Shelter Island Country Club has a BBQ buffet on Thursday nights which is nice. I don't know what your price range is, but Sunset Beach is pricey. You should take the ferry to Greenport and Sag Harbor. If you go to Greenport, you won't need a car, can just walk around town. If you want to go to Sag Harbor, you definitely have to drive. Both have some cute shops and restaurants. Your children will enjoy the Whale's Tale for mini golf. I think you will like Dering Harbor. Pridwin looks like it hasn't been updated in quite sometime. The beach is nice, but bring water shoes. The sand is not soft at all, pretty rocky. But still a nice beach. I love Shelter Island, I vacation there every summer. Fortunately family has a home there. Enjoy!

7. Re: Best play to stay on the island?

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