Shelter Island, NY

Optimum Seasons:  Summer

Gallery

It is a crime to be a resident of New York City and never have visited Shelter Island in your life.  I was inspired by a NY Times Article a friend linked me that gave an itinerary for the day.  Here is everything you need to know:

1)  Even though the ferry price is listed as $11 per vehicle one way from both the Greenport (North Fork) and Sag Harbor (South Fork) ferry services, it actually costs $13 per vehicle from Sag Harbor.  So if $2 makes a difference to you, do your round trip through Greenport.  Also, they charge per car per person.  So $11 per car plus $2 per person.  

2)  The North Fork of Long Island is picturesque and full of vineyards and farms.  Something to see in your life at least once.  But the South Fork is where all the action is.  The Hamptons are here!  There is a large and wealthy population!  Not only are there beautiful shops and towns and homes, but there are scenic vineyards and farms that rival those of the North Fork.  We took the Greenport Ferry to Shelter Island and the Sag Harbor Ferry back so we can dine at Il Capuccino (Amazing Italian food!!!  The big draw here is the complementary garlic knots they bring to the table.  And I also enjoyed my ravioli with pistachio sauce!) I was not satisfied with the Italian options on Shelter Island itself.  And there is no real charming Main Street on the Island (at least not that I found).

3)  As soon as we got off the Greenport Ferry in the morning, we drove up the hill to Marie Eiffel Market (which has an outdoor deck facing the harbor) We had our chocolate croissants and iced coffee facing the harbor and yachts.  I highly suggest getting your first bite here before you start your day on the island!  The cafe is one block down the hill from the newly renovated and quaint Chequit Inn.  This hotel is no place to go with young children as it is not stroller accessible.  And if you go here, go when it is a bit more affordable on a weekday.  If you want to make a road trip out of Shelter Island, I would totally stay here.  And the beautifully landscaped outdoor restaurant faces the harbor.

4)  After we ate at Marie Eiffel, we went to Picozzi's Bike Shop right around the corner, parked our car in the driveway, and rented a bike for one hour for $15.  Each bike comes with a helmet and a basket, but be careful to store your mobile phones in a bag as they can slip out.  We biked around Dering Harbor and Shelter Island Heights.  Look at a map and stay by the shoreline to see all the exquisite homes.  And remember, if you are not fit like me, be prepared for lots of hills and a spare oxygen tank in your car upon return.  I almost died.

5)  Have your bathing suit on and towels in a backpack that you place in the basket during the bike ride.  You can stop by Hay's Beach (free and much more private than the main draw: Sunset Beach).  There is no night life or restaurant here.  Just you and the sand and the water.  We didn't have towels so we couldn't relax here after a strenuous bike ride.  And if you don't want to rent a bike, you can still access Hay's Beach by car.  There are a few spots to park and it doesn't get crowded.  Spend a couple hours here before heading to Sunset Beach.

6)  We got to Sunset Beach by 1:30 and stayed four hours.  The sun would have set by 8:30 and my husband and I wanted to get back home for the kids. Otherwise, I'd have stayed here all day to catch the sunset and the alleged bumpin' night scene.  This beach is right across the Sunset Beach Hotel and Restaurant.  Onlynly permitted cars are allowed to park on weekdays (after 5pm, all cars can park).  Only permitted cars can park on weekends. However, if you drive down about 1/5th a mile, you will find free parking for all (to save some energy, make sure to drop off your beach chairs in the front and have your spouse park the car).  

So what can I say about Sunset Beach?  You feel like you are in the south of France when you are really just sandwiched between the North and South Fork.  I have seen charming beaches along the North Shore of Long Island. But nothing matches the crowd and vibe here.  You will feel like the Princess of Monaco.  Also, you can come here with your children (but my guess is those who did with young children either reside on the Island or were staying at a hotel).  There were paddle board rentals for $35 per person per hour and $60 per hour for two people.  If my husband and I weren't beat from the bike riding, we may have done this!  Also, we went on a 78 degree and sunny day.  The water was totally swimmable and clean and was the perfect temperature.  We forgot our beach umbrella so the cabana boy gave us one that belonged to the hotel and we tipped him a couple of bucks.  Also, I ran into a group of women who had ditched their husbands and children to enjoy a day here.  This doesn't have to be just a family oriented or romantic trip.  You can do a girls or guys day too!!!

7)  My husband and I were not entirely impressed with the menus at Sunset Beach Hotel Restaurant and the Pridwin Hotel restaurant (right down the block and also across the beach.  Even though they are both trendy...we did not want to eat fish after a long, arduous day.  But if you are good with being hungry your whole life, I highly suggest going to Shelter Island on a Wednesday in the summer to experience the all you can eat dining experience at the Pridwin Hotel (pictures included in the gallery).  The all you can eat is $42 per person and starts at 6:30pm.  It includes drinks and draft beer.  But no alcohol (keep dreaming!).  I checked out the buffet and it was mostly seafood which we don't eat.  So I skipped out on this otherwise amazing opportunity.

8)  As mentioned above, we left Sunset Beach early to dine at Sag Harbor, which is an adorable and historic town on the north part of the South Fork. The main street here reminded me of that of Greenwich, Port Washington, and Northport all fused into one.  I prefer the Main Street in Westhampton Beach, to tell you the truth, but this one is on the harbor and totally adorable in a different way.  You must see it if you do a day trip or road trip to Shelter Island.  Also, we dined at Il Capucino because we were in the mood for Italian food.  But there were far trendier restaurants along the Main Street.  Research before you go.  Every place looked super cute!

For a list of other beaches, click here.

Don't forget to check the gallery above (best viewed on desktop for captions), videos below, and add your feedback in the comments section! Follow me on Instagram and Facebook to see my next adventure!  And share with your friends if you appreciate this page.