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

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Yes, Shelter Island is surrounded by water and there is no convenient connecting bridge, but it only takes about five minutes to cross from either Greenport to the north or North Haven to the south. North Haven is next door to touristy Sag Harbour which we cycled to for lunch. Sag Harbour is that close. Shelter Island is as serene and peaceful as the Hamptons is not.

About a third of the island is covered by the Mashomack Preserve, and the rest of the island is full of trees, starry skies and the occasional Osprey.

Here’s a beach we went to at lunchtime on one of the busiest American holiday weekends. I rest my case.

This is an island where people go to the post office to pick up their mail, an island without traffic lights, an island without traffic. Shelter Island is about 27 square miles with under 3,000 full-time residents, many of whom can date their ancestors here back to 1776. The island has a small-town, old-fashioned feel.

That either floats your kayak or it doesn’t.

Just because Shelter Island lacks the flash and splash of the Hamptons doesn’t mean that it’s dull. I went with my boyfriend Ken who is a planner with a capital P.

We went sailing, kayaking, biking. We cycled past farmers’ markets, Victorian houses and minimalist barns.

We squeezed in a few excellent pilates classes.

But I drew the line at paddle boarding. We listened to live jazz at the picturesque Ram’s Head Inn one night.

We even gave Andre Balazs’ hip Sunset Beach a whirl for dinner. It was fun, but I preferred it at breakfast. The eggs were delicious, and the crowds were asleep.

Our favourite dinner spot was the popular Vine Street Cafe. Don’t miss the heirloom tomatoes if they’re in season.

We stayed at the charming Chequit, the  newly  re-opened, 37-room boutique hotel, which first opened in 1872. During its heyday in the fifties the centrally-located Chequit is rumoured to have hosted Frank Sinatra, JFK and Miss Monroe amongst others.

No such celebrities spotted anywhere this time, unless you include Marie of the Marie Eiffel lifestyle brand, a real rags to riches local story. Marie came to Shelter Island ten years ago after a debilitating car accident requiring 13 operations left her penniless and addicted to painkillers. She went cold turkey, opened a tiny consignment shop. A designer leant her clothes to sell, Marie borrowed hangers from a dry cleaner and hung the clothes on nails on the wall. Racks were too pricey. Business was initially slow save for one kind customer who came in every Sunday night and  asked,

How’s business?

and bought enough to keep Marie going for another week. That lasted two years. Eventually, Marie got a bank loan, and now owns three shops on the island and one on Sag Harbour. As she says,

The rest is history”.

Marie works 13 hour days, seven days a week and has the biggest smile on the island.

After four action-packed, exhilerating days it was time to wave goodbye to Shelter Island and brave that long ferry ride back to another world.

July, 2015

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