Powerboat Cruise To The Hamptons


By Rich

All of the creative talent in the Screen Writers’ Guild couldn’t have conjured better weather conditions for the one weekend this summer when we planned to leave Le Saberage on the mooring and climb aboard our good friends’ Hinckley Talaria 44 for a weekend of power boat cruising. Threatening forecasts to the contrary, we stayed almost 100% dry the entire weekend. Better still, the winds remained almost flat calm every time we needed to make a run to the next destination. The sailboat would have been slow, rolly and dull moving from place to place but the two big turbo Yanmars made nice quick work of each trip at 23 knots. We missed out on absolutely nothing in the way of sailing and covered much more ground than we could have motoring with sails under their covers aboard Seb. Lucky, lucky, lucky!

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I lobbied strongly to make Sag Harbor our first destination so that we might relive fond memories of our visit there a few years ago. The 50+ mile trip would be tough to fit into a sailboat cruise from Newport in a single weekend but even with a late morning start the Hinckley got us there in time for a late lunch.



Apart from being generally scenic, Sag Harbor offers some of the best people watching of any of the New England destinations we have visited. It’s one of the “it” summer destinations for wealthy New Yorkers who need to get away from Manhattan so they can unfold the colorful tail feathers of their fantastical wealth in a new locale. For those of us of more meager and humble means the spectacle makes for a great show. As I did growing up in this part of the country, I remain baffled that people with so many material advantages can appear (be?) so unhappy and take themselves so seriously as they go about their weekend leisure activities.

For those who enjoy (power) boat porn, Sag Harbor is certainly not bested by Newport but it does give far more direct dockside access and it attracts a great mix of boats. In the photo montage below, there is a little visual Easter Egg for readers with a keen eye: apparently one wealthy owner wanted to be absolutely certain of the availability of shore-side transportation wherever s/he traveled. It’s amazing that some individuals who walk the face of this earth need this level of creativity in burning off unneeded excess wealth.

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Friday night we took an evening cruise around the north tip of North Haven Peninsula and shut down the motors to take in what may have been the best sunset of our 2015 cruising season.

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Saturday we made a quick trip to Montauk, ducking in briefly to take in Fort Pond Bay just before arriving.


We tied up at the Montauk Yacht Club, which is actually a resort that is a “club” in name only. Here we encountered the biggest change in marina culture we’ve seen all summer. Dominated by large and expensive sport fishing power boats, Montauk Yacht Club is frequented by a clientele with a heavy “Jersey Shore” presence. Each yacht is boxed in with a couple of feet to spare on either side, leaving only a view of the dock and the neighbors. Like the “club,” many of these “boaters” seemed to be mariners mostly in name and seemed very content to hang out on the back porches of their yachts for the majority of the weekend. It’s sort of an urban version of boating.  The resort amenities of the marina certainly were luxurious, but I still didn’t quite ‘get’ the scene.


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Montauk Yacht Club was a little strange and while we’re very glad we came and saw it, this power boat marina scene wasn’t anything like a cultural fit for us.

Sunday we put cherry on top of our weekend by making a calm-sea run to Block Island for one final lunch at The Oar before returning to Newport. What a novel sentence for a sailor to key into a laptop: we quickly popped over to Block Island for lunch.

It was late enough in the season that the docks were mostly empty and we noticed a big change in the makeup of the crowd from partying power-boaters to sailing cruisers getting in one final jaunt with the family before the start of school.

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With full bellies and smiles on our faces, we jetted back to Newport to close out the weekend. At the same time, we put a figurative bow on our 2015 Newport-based New England cruising. Next weekend, Le Saberage is scheduled begin the trip home via a slow  September cruise of Long Island Sound.

2 thoughts on “Powerboat Cruise To The Hamptons

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