Sailing the Vineyard

August 26, 2023  •  Leave a Comment

On my recent trip to Marthas Vineyard to visit family, I had the wonderful opportunity to sail nearly half way around the island  from Vineyard Haven to Menemsha aboard the sailing vessel Mia. It brought a whole new perspective to some of the spots on the island that I had seen before but not from this vantage point. It also brought into focus just what it takes to captain one of these beautiful vessels and maneuver it through changing waters dotted with multiple other boats large and small enjoying their day out in the Vineyard waters. I certainly would never be up for the task!

I'll take you out into the waters via the photos I was lucky enough to get along our way. With winds blowing and boats rocking, it was a challenge holding steady for photos but thanks to great Ricoh technology, I managed to have a reasonable amount of success. Even on such a clear & bright sunny summer day, in many cases I had to push ISO to >1600 in order to shoot fast enough to minimize blur.

I'll start of with 3 photos of the boat herself so you'll get a good idea of how spectacular our little voyage was. 

For each and all of the photos, please click on the thumbnail and you will be redirected to the gallery where you view the image full size as well as purchase the image (or any other on my website) in a wide variety of formats from reprints, calendars, coffee mugs, canvas prints and so much more!








The Route

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We started our day at the Vineyard Haven Marina, where the MIA is moored when she is not out on the water. The harbor was just abuzz with activity as one would expect for a lovely summer afternoon!


Sights in the harbor in Vineyard Haven


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While boarding and preparing to get underway, we were graced by the beauty of some of the finest boats around, which included the Schooners Alabama and Shenandoah, both part of the Black Dog Tall Ship group. Both of the beauties are available and certified for coastal cruising not more than 20 miles from a harbor of refuge. Please check out their website for more details.

A few years back, we were so very fortunate to be in the right place at the right time to spot the Alabama up in Provincetown where she was preparing to depart on her voyage back to the Vineyard. How beautiful she was after raising her sails and setting her course!


The Schooner Alabama - One of the Black Dog Tall Ships


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We made our way slowly out of the harbor bearing in mind all the heavy traffic and the shout outs by the harbormaster to the misguided boaters ignoring the no-wake markers in the harbor. Be in on the road or thew water, there will always be those who feel safety rules do not apply to them, but that's a story for another day!

We followed the route under sail out into the sound that mirrored that of the Steamship Authority into Woods Hole. Two of my favorite lighthouses were along our path and finally within distance to get a couple good shots. The first (on the left) is West Chop Lighthouse which protects the west entrance to Vineyard Haven and on the right is Nobska Light with sits atop the bluff in Falmouth, overlooking the sound.


Lighthouses in the Sound


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We continued on a heading seemingly to Woods Hole but of course we were headed that way merely to keep the sails up and the wind on our back! To make our way to Menemsha, we turned our course more south, southwest, into the wind and on diesel power. As we turned, we crossed path with one of the most beautiful boats on the planet: a Grand Banks Yacht!



We sailed south/southwest along the northwest facing edge of the island, an area I had never seen before and an area which is dramatically different from the rest of the island: heavily wooded and steep facing hills and sand leading down to narrow and rocky beachfronts. You can see from the photos below the terrain you're dealing with along the shore, the stairway from nowhere, the rocky beach and the homes cliffside.


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Continuing along the route provided us with some spectacular views of the sheer cliffs and the multi-million dollar homes perched along the dunes and hidden in the vegetation. To drop a couple names, the homes of John Kerry & Martha Stewart are along this stretch of waterfront.


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One of the more memorable and historically significant sights along the way is this tall, iconic spire rising 45 ft towards the sky. 

"On the craggy northwestern coast of Martha’s Vineyard, a roughly 45-foot chimney rises above the shoreline like an oversized maroon candle on a rubbly birthday cake. For mariners, that chimney in the sleepy town of Chilmark has long been a marker for plotting courses across Vineyard Sound. For decades, it was the most visible aspect of 18 overgrown, seldom-visited acres." Courtesy

The Brickyard was one of the earliest brick-making operations with much of their production going to help build the city of Boston. Please take a few minutes to read about the significance of the Brickyard here and here. Thanks to the Trustees for keeping the history alive and allowing the public to witness it as well!



What Gilligan would be foolish enough not to provide snacks for the 3 hour tour, the 3 hour tour!

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If you don't know where you came from, how will you know where you're going?


Coming up on our destination: Menemsha Harbor.



Coming up to Menemsha, the beach, the harbor and waters around were abuzz with summertime activity. There are few places quite so captivating and idyllic as Menemsha, It has maintained its historic fishing roots, albeit, significantly diminished. It is the 'go to' place for sunsets across the beach where, on any given early evening, you'll be parked at one of the last remaining drive-in theaters, showing repeats of the same nature movie night after night....but not one of them ever being the same.


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Once into the harbor, it is a feast for the eyes; sensory overload! The beauty of this harbor and the postage stamp town cannot be described or understated. 


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Once we disembarked, it was time to hit the market and prepare for dinner and wander around 'town' before hitting the pavement back to Oak Bluffs. If you've ever spent any time in Menemsha, you'll know that your first and usually only stop for fish and seafood is, of course, Menemsha Fish Market. Great fish, great prices and service that will astonish you! The $20 lobster roll ain't too bad either! Our menu, for the second night in a row, was of course lobster! (among other delicacies)


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A short walk around town and across the harbor reveals a plethora of hidden treasures and photographic opportunities galore!


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I hope you've enjoyed our little sail around the horn  and if you haven't visited this neck of the woods, I hope that this photo tour will provide you with the incentive to get out to the island.















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