Orient Point/Shelter Island


Shelter Island is one of our favorite weekend spots, and Labor Day weekend 2009, we headed to Shelter with Bernie and Joe Abbagnaro of Luffin’ Life.

We anchored at Orient Point on Friday night and it was perfect.  It is part of Orient State Beach, and while there are no provisions on land whatsoever, it’s a great place to get away from it all. A curious, yet shy harbor seal, greeted us at the anchorage and a beautiful sunset colored the evening sky.

Saturday morning was warm and we dinghied to the beach (to walk Shelby) and collect some shells.  Note the beach is not sandy (beach shoes are a must), and not great for lounging unless you bring chairs. However, if you like to collect shells and other beach treasures, this is the place for you. If you have little crafters aboard, they can collect a whole trove of beach treasures. Don’t forget to bring along some paint, glue and string so they can be kept busy for quite some time creating lovely works of art and beach jewelry. These items could also make for a good seafaring scavenger hunt to keep the kids entertained. (Heck, add some grog and it could be a fun adventure for adults too)!

After breakfast and an early morning swim, we weighed anchor and motored to Shelter Island’s Dering Harbor, where both boats took moorings at Pecozzi’s. I like Dering because though it’s a small town with just a few shops, I can find just about everything I need for a fun weekend.  So, you can decide last minute to cruise over there, and really don’t have to pack a thing.

One of the first stops in the morning when we walk Shelby is the Redding Gourmet Market. They open at 7:30 am.  You can get good coffee, cappuccino and fresh baked goods (the cinnamon rolls are excellent). (This time, we played Aldo (from Block Island) and dinghied some warm and gooey morning goodies to Luffin’ Life as we yelled “Andiamo”  The Redding Market also offers meat, fish, artisan cheeses, prepared gourmet food and groceries.  There is a wine shop across the street (just in case you run dry.  NYS does not have blue laws…meaning you can buy wine and liquor on Sundays too).  Next to Redding’s are a gift shop with tees, sweat shirts and other sundries, and Jack’s toy store/hardware with all the water toys and pirate gear that a sailor of any age could want.  (By the way, up the road is an Ace Hardware store for more serious needs).

If you forget your bikes, you can rent from Picozzi’s (just across the street from the marina).  Maps of the Island are easy to come by.  The roads are generally smooth, and the terrain is varied for a nice mix of uphills and coasting.  Once you get away from the harbor (and ferry) area, the traffic lightens considerably.

Just up the road, over the bridge to the left is a quiet little green that is a nice area for yoga, or if you are traveling with kids…tag or whiffle ball, etc.

There are plenty of restaurants within walking distance of Pecozzi’s.  Dory’s is casual and has a nice bar. Generally, on weekends, they offer live music in the afternoons and evenings. They have an outdoor deck that seems like it would be a great spot for afternoon drinks.  We have eaten at Dory’s a few times -- both casual burgers at the bar and finer fare in the dining room.  Both were good.

The Chequit Inn, built in 1872, is a charming Victorian country inn on Shelter Island.  Their restaurant is supposed to be excellent (it’s open daily year round), but we have not yet tried it.

This time, our foursome ventured to Sweet Tomatoes, just up the hill from Pecozzi’s, for some excellent Italian food!  The company was even better!!!  The new manager claims that the first thing he did when he took over was toss out the freezers.  All the food is fresh.  I honestly am not a big fan of going out for Italian food, but I would definitely go back to Sweet Tomatoes…it was that good!

There are numerous other restaurant choices.  I hear from several sources the French bistro, Sunset Beach, (near Crescent Beach) is awesome.  You could definitely bike there (it’s not that far), but after a few cocktails, I’d be hesitant to bike back.  Taxi would be the more relaxing option.

One reason, we have never fully explored all the restaurant options on Shelter, is the fact that getting to Greenport via a short ride on the North Ferry is so easy, and it expands all your options. (A weekend simply isn’t enough).  From Picozzi’s, it’s a short walk to the North Ferry and all the dining and shopping that Greenport offers. On several visits, we have biked to Sag Harbor (via the South Ferry), which opens up all the dining, shopping and BIG yacht ogling options the Sag has to offer.

The wind was blowing on Sunday morning.  Carpe diem -- we dropped our mooring, hoisted sails and set course for West Neck Harbor, where we dropped anchor and had sunset cocktails. West Neck looks to be a very nice sandy beach. We will probably explore this area in more detail next time we visit.  After some lovely photo ops, we headed back to Dering, and picked up our mooring at dark.

-Mark and Maria Reilly - Bela Luna

⟵ Back to Ports of Call