Cruising the Connecticut Coast

The week after Labor Day has become my favorite time to go cruising. School is back in session, crowds of tourists have all but returned home, but the weather-if you’re lucky-retains most of its summer warmth.

With a storm brewing to our west, blocking popular destinations like Block Island and Newport, Karen and I cruised east burning up some vacation time while discovering what else our new home state had to offer. From Clinton and Branford, to New Haven and Westbrook, we learned that Connecticut (a drive through or past state for many people) is filled with charming anchorages and cities on the rise.

I hope you enjoy some of the photos from our adventure, but more than that, I hope they inspire you find that new destination near you that might be hiding in plain sight.

 

The Truth About Fishers Island

The local residents of Fishers Island, New York have an online reputation for keeping to themselves and treating tourists like flesh-eating vultures. So it came as a surprise when, just moments after tying our dinghy up to Pirates Cove Marina, a woman walking by turned to Karen and I and asked, “Do you two need a ride anywhere? I’m heading across town.” I guess, just maybe, not everything you read on the Internet is true [gasp!].

We declined the kind offer and set out to explore the island on foot. How’d she even know we were visitors? You have to let everyone know you’re a tourist, I told Karen as I adjusted my large Canon camera around my neck and the backpack on my back.

“Mhmm, yeah, I’m the tourist,” she replied. 

As we wandered the quiet, wooded streets we came across a number of locals who all greeted us not just with the obligatory mumble and head nod, but with actual smiles and articulate greetings.IMG_9360_1

Another misconception about Fishers Island is that the population is made up of blue-blazer and bow tie wearing seniors. And while that demographic is represented, the island offers much more diversity. We found this to be especially true when we stumbled onto a beach on the west side of the island where (at least) a hundred young people threw back red solo cups and tossed frisbees.

“Well, that’s different,” Karen suggested.

The rest of our day would be filled with requisite cocktails and an alfresco cookout. Afterwards we’d take the dinghy into the Fishers Island Yacht Club and set out in search of ice cream. One rule we’d made up that challenged this time-honored tradition was that we couldn’t use our phones to look at a map. We’d have to actually explore the town the old fashioned way.IMG_4599.JPG

The summer sun was setting, casting long shadows onto the quiet streets. The well-manicured landscapes and colorful homes with wrap-around porches gave you the feeling that you travelled back in time. Furthering that illusion was a gang of boys and girls tearing through town on their bikes. When was the last time you actually saw kids enjoying a bike ride with other kids? It was a welcome sight.

On a hunch, we followed their general direction until we were all reunited at Toppers ice cream shop, a pet-friendly hot spot in town where all the local kids hung out. If you were to take the phones from their hands, the scene would look like something from a 60’s movie.

We’d spend the rest of the weekend kicking back on the beach, exploring the island’s other harbors and generally enjoying some R&R.

A swift, Sunday sail later and we were back in Essex and preparing for the week ahead back in the real world. It’s funny,  I’ve probably passed Fishers Island from the water dozens of times, and because it didn’t have one of those popular destination names like Cuttyhunk, Shelter Island, or Block Island, I—and I suspect many boaters—never paid it much attention. It really is a gem hiding in plain sight.

So, if you’re looking to escape the world for a little while and slow things down on an island with small town charm to spare, a weekend on Fisher’s Island can be as refreshing as a cone of mint chip ice cream on a hot summer evening.

Just don’t tell the Internet.

The Journey.

Boating is, in many ways, a suitable metaphor for life. In both, there are times when the sun’s shinning and you’re cruising in calm conditions that you think’ll never end. Then there are times when—out of nowhere—the wind picks up and you’re braced, white-knuckled at the helm, fighting mightily in vain to get your bearings. In the end you hope the good days out number the bad, or at least break even. And along the way you’ll come across characters of all types and sorts. If you’re blessed, like I’ve been, the people that mean the most, your family, will stay aboard with you for as long as they can. Friends and colleagues, well, they’ll come and go.

You’ll spend some time in stunning destinations, making connections that’ll shape you in ways you never expected, and you’ll also find yourself in spots so miserable you’ll find yourself praying for the tide to change so you can leave it in your wake.

There will be times where the boat purrs like a kitten and the brightwork glistens into the eye of all those who pass it. Beautiful! Some will proclaim at the sight of her. There is always a lot of praise when you’re up on top. Then there are times where things are breaking left and right; leaks spring up from everywhere, the floorboards get rotted. You pull up the carpet and put away the fluffy pillows. Tools and drops of sweat are scatted everywhere. Frustration is high, and there’s not a soul around to help.

But you stay focused, work hard, and with a little luck smooth sailing finds you once again.

In life, as in boating, it’s important to find a partner, a first-mate of sorts that will stand by you not just in the good times, but in the bad. After all, what’s the point of embarking on an epic adventure if you have no one there to share it with?

Over the last four years, Karen has proven to be such a partner. From convincing me to buy the boat, to spending hundreds of hours sanding, packing, painting, priming and pumping out endless moral support, without her, none of this sailing adventure would be possible. I’m excited to announce that last weekend, on a picturesque afternoon in Hamburg Cove, Karen agreed to marry me and stay on this adventure for the long haul.

I feel like the luckiest guy alive and I’m extremely grateful to be on this adventure with her.

Photo of the Week:

I thank god for my life
And for the stars and stripes
May freedom forever fly, let it ring.
Salute the ones who died
The ones that give their lives
So we don’t have to sacrifice
All the things we love
–Zac Brown Band

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Old Glory waves as the sun sets behind Fisher’s Island, New York.