Thursday we backtracked 6 miles to Coecles Harbor on the east side of Shelter Island, where Russ claims “50 years” and is one the first places we ventured to in our first boat (together) m/v Lady L. Most of the harbor’s southern shore is posted “no landing” as the entire area of many acres is a preserve. Only a small section on the north side of the narrow entrance is available for beach combing or fishing.

Osprey nests sat safely on man-made nest assister poles, complete with a lookout perch. The adults appeared larger than usual but that could just be a proximity thing.

The most noteworthy thing is the island in the island in the island; namely Taylor Island sits in Coecles Harbor on Shelter Island on Long Island.

Of course if we’d seen a sleek Billy Joel designed Shelter Island Runabout (similar to a dark-hulled Grand Banks Eastbay picnic boat), that would have been worth a mention and a photograph. The boats are built right here at Coecles Harbor Marina.

Taylor Island, fka Cedar Island, and its lone log cabin house have an interesting four-era history which we first began to read about in ActiveCaptain reviews, then Russ dove in further via all-knowing Google. I’ll give you the basic overview and a link to more for those so inclined to knowledge consumption.
The log cabin main house was built by F.M. Smith, the Borax king, who purchased Cedar Island in 1899. He used the cabin for entertaining, often hosting clambakes. In 1939 S. Gregory Taylor acquired the island, adding a bedroom, kitchen, a tower, heating and running water to the house. Mr Taylor died in 1948 and wished to be buried on the island. He willed the island to his nephew Steve and upon Steve’s death the property would belong to the Town of Shelter Island for the use and enjoyment of the people. One day, circa 1958, Andrew Arkin was flying around Shelter Island looking for property to purchase when he flew over the Taylor House. Within no time Arkin obtained a 5-year lease at no-cost from Steve with the agreement that Arkin restore the Cape Cod house and small generator house and allow Steve’s mother, Mr. Taylor’s sister, to visit her brother’s grave when she wished. This lease lasted 22 years and when nephew Steve passed away the property went to Shelter Island.

If you read the link, click the History button and be sure to click the name and dates hyper-link on the Andrew Arkin tab to read his interesting letter about finding the island and becoming a Shelter Islander.

Today, eight years into a restoration project, the house is protected by a new sea wall and you can peer inside to see a gorgeous vaulted ceiling, substantial fireplace and a cute kitchen with a gas fridge.

Respectful visiting is allowed; so we did, bringing our happy hour fixings over for drinks on the porch. At low tide you can walk or drive across the sand bar that connects the island to Shelter Island. We used the floating dock.

Friday was a 1 engine motor around the north tip of Shelter Island to Dering Harbor situated on the NW side. Tucked into the harbor are more moorings than you can wave a flag at, belonging to the SIYC, Piccozzi’s Marina, Jack’s Marine (and Hardware) and private owners. We didn’t have any trouble reserving a mooring with Jack’s Marine whose rate was a more reasonable (this is the north and New York remember) $50/night than Piccozzi’s, and my dears you KNOW we do not belong to any yacht club. Well, maybe that DRYC might count. 🙂 Plus, we have a thing about the name Jack.

From here we could spend time “in town” on Shelter Island as well as ride the ferry across to Greenport. Four to six ferries run every 15 mins back and forth so if you are not in a vehicle, the wait is negligible and we managed to just walk on both trips.
Greenport, on Long Island’s North Fork is well known for Claudio’s restaurant and the family’s expanded empire: Crabby Jerry’s on the east Pier and the ultra-popular Clam Bar on the West Pier. Greenport was always a favorite family visit in our power boat days; less than two hours from Essex/Old Saybrook made for a quick trip. With our Brewer’s card we could get free overnight stays at Brewer’s Greenport where the shuttle would drive you into town. If we were lucky, the Firemans’ Carnival would be taking place and our son could enjoy rides and fried dough (us too!) We watched as the carousel got moved several times, finally landing at Mitchell Park. It’s the kind with brass ring grab so you’ve got to be quick to snag an outside ride and quick to grab a ring as you pass by. I think getting the brass ring got you a free ride.
For me though, the main event is Shelter Island Height’s hilltop centerpiece, the Chequit Inn, a short walk up from Dering Harbor. Lunch outside, under the canopy of a perfectly situated stately tree is the ultimate summer dining experience.

We arrived early enough Saturday to select the best table- not too much sun and a pie slice view of the harbor. A nice man at a nearby table offered to take our picture. Water and our Cucumber Lemonades were served in canning jars; how many upscale places can pull that off? Cucumber looks to be this summer’s drink ingredient… and I love it. Chequit cheated and made their drink with Effen Cucumber Vodka and a quality lemonade, while Restaurant L&E in Chester, CT wowed us with their Scottish Lemonade. Hendricks gin, muddled cucumber, lemon juice and simple syrup. And you know, the drink tastes just as good with the gin of your choice.

Walking was a must as well as checking out the shops offering beautiful everything!

Saturday finished with a bang; fireworks off Crescent Beach to our west and only the very low ones got blocked by the hillside that separates Dering from the ferry dock and beach area beyond.