Elena Bowes

New York-London design & culture writer of a certain vintage looking for meaning and wholeness in life

Shelter Island Take Two – Anticipation & Adventure

July 9th, 2016
Shelter Island, Long Island

Sometimes a vacation is so great that you just can’t wait to repeat it. And sometimes a vacation is so great that maybe you shouldn’t repeat it. Don’t tempt fate. Don’t toy with a good thing. Expectation can be dangerous.

I always tell my jubilant sister Diana to expect nothing when her birthday arrives and that way she’ll never be disappointed. Does she look like someone who would listen to me?


When my boyfriend Ken asked me if I’d like to go back to Shelter Island for the Fourth of July weekend, I forgot my ‘expect nothing’ rule and only thought of Carly Simon’s Anticipation song – for a good six months.

When the day finally rolled around, I packed a carefully chosen picnic for the evening ferry ride  from Bridgeport to Port Jefferson.

A ferry can be romantic,


until it starts moving. The selection of salads blew – not so carefully – everywhere, and in the dark. The plastic cups were no match for the sea breeze. I could feel the chilled Rose splash against my calves and ankles. I was shivering in my summer dress. And  I’m not going to discuss what havoc ferry wind can wreak on a Bergdorf blow dry.  When we got to the Chequit Inn–  hungry and thirsty with matted hair- we found our “upgraded room” had a view of the hotel’s numerous air conditioners.

Hmm, I thought. Maybe encores should be left to the theatre.

The next morning the perky staff moved us from Suite 1 (avoid) to Suite 20 (request). The best room of all (Suite 21) – the one we had last year with a view of the sea and oodles of space – was taken. The hotel’s terrace restaurant was open and looked inviting. We de-stressed at Shelter Island Pilates (highly recommended 2nd year in a row), bike rode to deserted Hay Beach (a two-year award winner), had drinks and watched the sunset at Andre Balazs’ Sunset Beach, and ate dinner with friends at buzzy Vine Street Cafe. We went there twice in five days, it’s that good. Another day we kayaked to scenic Big Ram Island, all repeats from last year.


So maybe, like a good relationship, familiarity isn’t such a bad thing. Getting to know a place and a person has its upsides. Not everything will be perfect, but that which is, is even more special.

Especially, when there’s a little danger mixed in to spice things up. We biked  to the Sag Harbor Golf Club and spotted a dirt path. Serene …


until you read the sign …


Don’t worry, it’s not hunting season, Ken laughs, peddling away.

Then what are these, I ask?


Old bullets. Don’t worry about it.

Ken is gone, and I’m both a chicken and a sheep so I peddle too, head tucked down in case of stray bullets. We follow a path to a gorgeous, deserted beach, only a few miles from bustling Sag Harbor.


Then we have a delicious lunch outside at the American Hotel – same menu as last year, same shirt too (Ken’s, not mine).


Another day my friend  Karen shows me her favorite parts of the island.


She and her husband Marc plus four kids have been coming here for a decade. He’s a big sailor. I never realised how much I like yachting life until I tried the yacht club’s Southside cocktails. Ahoy Captain!

Karen thinks Nostrand Parkway has the prettiest houses.


and Kyles the best doughnuts.


She gets a lot of her fruit and veg from organic Sylvester Farms.



For a gorgeous walk Karen took me to Mashomack Preserve which covers a third of the island. It’s so peaceful and beautiful that we got totally lost mid-deep-chat. She could see that I was slightly panicked about being lost.


No problem,  says Karen, I’ve got my phone. Oops, it’s out of juice.

Then she starts swatting her legs.

Look at these ticks. Jeez.

Isn’t this the capital of lyme disease? She casually brushes off about twenty from her body and then spots two on me. Where are the other 18, I wonder??? First bullets, then lyme. What next?

We eventually found the path back, went for a swim at Secret Beach whose location is, well, a secret. And as for the ticks – that’s where Ken comes into his own. Who knew he was such a talented tick inspector?

July 2016