Meet Dennis Flaherty

Not everyone can say their retirement dream involved 1,000 nautical miles, a trusty sailboat, and only eight gallons of fuel. But then again, not everyone is Dennis Flaherty. For Dennis, Cape Cod has always been about the pull of the ocean, the rhythm of music, and the joy of community. From summers spent living on a boat in Waquoit Bay to late nights singing with friends, his life is a celebration of everything that makes the Cape feel like home.

Dennis’ story is so Cape Cod. Sailing and music - two of his greatest loves - shine through in every part of his life, and they’re a big part of what makes this place so special. I especially loved his description of sailing as a “passport.” We were immensely grateful to be invited along for a sail with him, and it was a truly wonderful day.

Dennis is a skilled sailor with the patience of a saint - no surprise, given his decades of teaching experience. As he guided us through the ropes (literally! - oops, I mean lines, of course!), we talked about sailing, music, and how Cape Cod came to hold such a beloved place in his heart.

We experienced a myriad of conditions: from "light air" with still, calm waters to brisk winds and heeling - it was both relaxing and exhilarating! 

We thoroughly enjoyed Dennis' company: he is a riveting storyteller, and we love his spirit of adventure. In his own words:

What drew you to Cape Cod originally, and what has kept you here? 

The short answers are: pretty girls (of legal age) in bikinis 👙 & sailing. ⛵️

The long answer is: 

I have always lived in Massachusetts, and have loved the Cape all of my life. The 1st ocean beach I remember my parents taking me to was Old Silver. In the summer of '78, I had the opportunity to get a mooring for my little 17' sailboat, "Volare'" in Eel River, East Falmouth. I was 23 years old, single (ready to mingle), and I had just completed my 2nd year of teaching elementary Physical Education in the Town of Medway. For the months of July & August, I lived on that little boat and I had a blast (the original Casino & Brothers 4)! The following summer I purchased a bigger sailboat (23')  and transferred my mooring to Waquoit Bay. I continued teaching in Medway until my retirement in the fall of 2011. All through my teaching years, I would summer on my boat on Waquoit Bay, and I knew that upon my retirement, I would move to the Cape full-time. In June of 2013, my dream came true and I purchased a home in East Falmouth. In 2014, I purchased a bigger sailboat (Cal 33') that I continue to keep on my mooring in Waquoit Bay. In September of 2019, I moved to Mashpee. 

Can you describe a favorite place or activity on Cape Cod that holds special meaning for you? 

Waquoit Bay where I moor my sailboat is simply magical! 

Sailing is a "passport" to being one with nature, harnessing the wind to reach beautiful destinations: the various ports on Martha's Vineyard, the Elizabeth Islands, anywhere from Cuttyhunk to Chatham. Last summer I covered 1,00 miles in my sailboat and only burned 8 gallons of fuel! 

How do you feel the different seasons on Cape Cod impact your lifestyle and activities? 

During all of the seasons, I have singing gigs. 

In the Spring I prepare my sailboat for the coming season. I usually launch my boat in early May. 

In the Summer the tourists arrive and traffic on the roads greatly increases. Another great thing about my sailing life is that I can get on my boat and sail away to less crowded places. 

In the Fall the sailing season is winding down, eventually the boat is transported to my driveway, winterized, covered, and put to bed until March. 

In the Winter I go for walks to South Cape Beach, a mile & 1/4 from my house. I do home improvements inside (outside on good weather days). 

Are there any local events, traditions, or communities on Cape Cod that you actively participate in or feel particularly connected to? 

I have 2 main circles of friends: boaters and musicians, and there is some overlap. 

Singing is very important to me. I was 9 years old when I saw the Beatles perform in February of '64, on the Ed Sullivan Show. Ever since then, I wanted to sing and be part of a musical group. It wasn't until I retired from teaching and moved to the Cape, that I realized that dream. I owe a lot to Bart Weisman. I attended one of his monthly Jazz Jams, I sang a couple of songs, Bart and I developed a friendship, and he started hiring me. After 10 years I now know many of the wonderful and talented musicians here on the Cape, and that is either directly, or indirectly because of my good friend Bart Weisman. 

Photos courtesy Provincetown Jazz Festival

Can you share a memorable moment or experience you've had on Cape Cod that captures why you love this place? 

I think that my above answers pretty much says it all... 

Indeed, they did! From setting sail across the Sound to raising his voice in song, Dennis reminds us that Cape Cod’s magic is found in both the big adventures and the everyday moments. Thank you, Dennis, for sharing your story - and for letting us all ride the wind and the music right alongside you. 💙

PS...If you're on the Cape, be sure to catch Dennis at Tomatoes in Sandwich – he’s there every Tuesday night for Sinatra Tuesdays from 6pm-9pm...

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