Summer in the Hamptons …and Martha’s Vineyard and Nantucket Island continues… Part 3 of 3

August 23, 2017

Locations we have visited and/or anchored during our tour of the Hamptons, Martha’s Vineyard, and Nantucket Island

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An advantage that we have had sailing from location to location for 4 weeks is the opportunity to experience and observe the uniqueness of each island and village as well as the common elements.   The historical aspect of the region is unmistakable.  Many of these locations were first settled in the late 1600’s and played roles in the founding and early development of our country and that alone has influenced the culture.  In several of the locations – Sag Harbor, Martha’s Vineyard, and Nantucket Island – whaling was the predominant industry in the late 1700’s into the 1800’s.  In these locations, there are beautiful homes that were originally built for whaling captains and are still private residences today.  Notably on Martha’s Vineyard and Nantucket, cedar shake siding, that has faded to gray, is very, very common.  One resident of Nantucket told us that this was preferred due to the impact and wear of the weather and salt water on regular house paint (the whaling captains’ houses, however, were all painted or brick).   The harbors and marinas, while different, also begin to look the same except I noticed that in some locations there seems to be more of one type of boat versus another (e.g. sailing versus power; newer versus classic) and I’m not sure why that was the case, except in Montauk.

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Example of architectural style of many of the whaling captain homes

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The barn-like roof and gray cedar shingle siding is very prevalent particularly on Martha’s Vineyard and Nantucket

The following are my observations of each of the places we visited and some pictures I took of each location.  This is not a definitive overview of each location since we usually only saw a partial piece of each island and town, and when we had the opportunity to explore further, always discovered there was more variety than we saw at first blush. 

Long Island and the Hamptons:

Our visit to Long Island was confined to the north side of the island, along the Long Island Sound.

Sag Harbor, NY:  We arrived in the town of Sag Harbor on our dingy and immediately encountered an extremely busy road that ran behind the marina with cars backed up – rush hour on the island. Locals told us that Sag Harbor has changed quite a bit in last few years with many more vacation homes being built in the area and summer congestion increasing greatly.  Walking up Main street from the busy road, Main Street is a mix of restaurants, shops, grocery store, the Post Office and a laundromat but a bit further on, there is an area of Captain houses, which are beautifully maintained, and the Whaling Museum…which is appropriately located in a former captain’s home.  Sag Harbor does not appear to be as focused on maintaining historical preservation as other places, such as Nantucket.

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Sag Harbor marina and harbor

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Sag Harbor Whaling Museum and originally a whaling captain’s home.

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Life on Sag Harbor…on a Sunday afternoon, a float plane flies in to collect guests from the yacht to return them home.


Greenport, NY:  Across the channel from Shelter Island, Greenport was one of our favorite stops.  It most resembles an authentic New England small town.  It feels as though it has not been discovered as a prime spot for a summer vacation home, like Sag Harbor.   Its main street and shops are beautifully maintained and it feels as though there is a local effort to maintain that small town, main street charm.

Montauk, NY:  Located at the very far eastern tip of Long Island, this is definitely a fishing town and all the sport fishing boats in the harbor were proof. The marina appears to be 95% sport fishing boats. Montauk is a prime location to get to good fishing grounds quickly.   Its main town was more modern, not located next to the harbor / marina and, in my opinion, not particularly charming.   We biked 8 miles up and down hills to visit the lighthouse and then climbed the narrow 137 steps to reach the top. It is the 4th oldest in the U.S, commissioned by George Washington in 1792.

Block Island, RI:  An island that lies further east from Long Island and is part of Rhode Island.  We anchored for 1 night and spent very little time to exploring the island.  However,we can highly recommend The Oar, one of Chris’ favorite spots, where we enjoyed some delicious Mudslides and played a very heated game of corn hole with Chris and Lauren, which Doug and I won, I might add.  Funny, that second Mudslide seemed to give me greater accuracy in my toss.  I’ll have to remember that in all future games.

Cuddyhunk Island, MA:  OK, seriously, who couldn’t love that name?!?   Cuddyhunk is a very, very small island that lies across Vineyard Sound from Martha’s Vineyard.  We anchored for 1 night and shared the harbor with a regatta from the New York Yacht Club, which included NALA, the 66’ HH that will be docked next to us in the Newport Boat Show in mid- September.   There is a small village on Cuddyhunk named Gosnold.  It is very small and charming and feels almost like an isolated oasis. Golf carts seem to be the predominant means of getting around the island.

Martha’s Vineyard, MA:  We sailed past Woods Hole, with its famous oceanographic research center onto Martha’s Vineyard.   We explored the western side of the island, or as the locals call it, down-island because it is at a lower longitude.   We really enjoyed what we experienced on Martha’s Vineyard and would definitely recommend it as a place to visit along with a side trip to Nantucket Island which is very close and readily accessible by ferry from the Vineyard.

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Martha’s Vineyard bike map. Rode from Edgerttown to Oak Bluffs to Vineyard Haven and back to Edgertown. .


     – Vineyard Haven/ Tisbury:  This was first port of call for us. It is the busiest port on the island and primary ferry entrance.  When we first arrived, it was bumper to bumper traffic on the road running along the harbor, similar to our Sag Harbor experience and not terribly inviting.   On our second trip to shore, though,  we wandered up the hill a bit and discovered a very lovely area of shops and restaurants and further along, very beautiful homes and quiet streets.

Edgartown:   The first colonial settlement on Martha’s Vineyard, that was established in 1642, Edgartown is best described as an elegant community.   Attention to historical preservation reminded me of Charleston, SC.  There are many preserved whaling captain homes and it’s obvious that there are building codes that insure newer homes conform and blend well with the historical structures.  Considering that tourism is the primary ‘industry’ on the island, its understandable why so much attention is paid.  I also think that the long- time residents have a lot of pride in their history and want to preserve that.  Edgertown was my favorite location on Martha’s Vineyard..

Oak Bluffs:  We did not anchor near Oak Bluffs but we visited this cute town a couple times – once to do laundry and the second time as a stop on our 20 mile bike ride from Edgartown to Oak Bluffs to Vineyard Haven and back.  Oak Bluffs strikes me as the more ‘funky / fun’ village – more like Tybee Island is to Savannah.   There seemed to be more partying going on around the marina than in the other locations and great nearby beaches.  Oak Bluffs became a popular destination for upscale African American professionals to build summer homes and form a community.  It has over 300 ‘Ginger bread style’ homes which are very distinctive, lovely and well-preserved.  They are a hallmark of this town.

Nantucket Island, MA:   Nantucket was our last stop on this tour before heading to Newport, RI.   This was my favorite location of all the many places we visited.   It is a beautiful, historically preserved town and island.   There are loads of tourists, many spilling off the numerous ferries that arrive every day during the summer.   This marina had the most boats of any we had visited, and a good mix of classic, modern, yachts and sail.   The Whaling Museum was awesome and worth a visit. I’ve visited to 3 or 4 whaling museums over time- this was by far the best, primarily due to the presentations made by the docents.  A short distance out of town and one finds a bucolic, rolling countryside with beautiful homes.   While we were there, the annual parade of Rainbow Cats (children’s sailing boats) was held as well as the Opera House Sailing regatta.  On that day, the harbor was buzzing with activity.   One unusual aspect of anchoring for us was the current running through the harbor.  It was so strong, it would outpace the wind.  Our instruments record the location of the boat while anchored and a screenshot of our anchored position over a couple days looks like a child’s scribbling as opposed to a smooth circle around the anchor point.    The waters were also filled with jelly fish floating by the boat – apparently an annual occurrence around this time of year.

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Nantucket Marina

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Nantucket Marina from the roof of the Whaling Museum

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Low tide

81817. Whaling museum. Nantucket

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Deb’s vote for most beautiful whaling captain home

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Not sure of the significance of these shoes but it looked pretty cool

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More whaling captain houses on Nantucket

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All the streets in the main area of the town were either cobblestone or brick. Wonderful preservation… not so fun for bike riding.

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Quaker burial ground. Apparently over 1000 people are buried here but traditionally grave markers were not added to graves. These were added in the 1800’s

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Rural bike rikde. This was driveway to someone’s private estate

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Widow’ s walk on newer homes was not unusual .

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At the end of our bike ride from Nantucket harbor to Madeket beach on the Atlantic Ocean

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Minnehaha moved around a whole lot while anchored in the Nantucket harbor.

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Picture of Doug taking video of jelly fish, as they swam by the boat, with his GoPro, which was NOT turned on.

Conclusion and adieu for now….

We set sail for Newport, RI on August 21 (eclipse day) where Minnehaha will get some much needed repairs and will be readied to be on display in the Newport International Boat Show from September 14-17.   I am planning a short trip home in the next few weeks to catch up with family (including 4 new babies, born to nieces and nephews, either just before we left or during our time away) and friends.  Doug will stay with the boat to oversee repairs and I will return for the boat show.   We will be leaving Newport shortly after the boat show and heading south towards Annapolis, MD where Minnehaha will again be on display during the Annapolis International Sailboat Show from Oct. 5-9.

As I write this, I am inspired to once again share how much I have loved waking up in the morning, looking out of the back of boat at the water and the sun slowly rising.  I love the views of other boats gently rocking nearby and the small towns surrounding the harbor.  It is so peaceful and soothing.   The view from my condo back home is also wonderful (I am blessed) but I have equally come to love this view.   It is wonderful to watch the world come alive.  The fishermen as they begin to head out early in the day; the first ferry as it enters a port; the fish jumping in the water around us and the birds taking flight.  It really is magical.   I am going to miss this when we are away –  but the memory will bring me back again for our next adventure.

I also have learned a very important lesson for myself.  I started this journey with a lot of anxiety and fear (I’ve written about this in an earlier blog posting).  Much of this anxiety was due to a fear of change in my life.  A change from the daily life with which I was familiar and loved, to a life in the great unknown.    I mourned that when I was younger I was much more open to impetuous adventure, sometimes naively and sometimes with bad results, and with years and experience, I had become much more cautious and reluctant to undertake the unknown. Oh sure, I’d still have my moments of spontaneity but mostly I had grown to seek refuge in the comfort of the routine and the known.  Fortunately, I have a wonderful partner, Doug, who made it possible for me to have this adventure.  And I had my own innate sense of commitment and courage, my belief that once I made a deal ‘to give it a shot’, no matter how much anxiety it provoked in me, I had to plunge ahead.  Thankfully those qualities were steadfast. As I reflect on this experience I have learned that I can adapt to change and that ‘change’ does not necessarily mean giving up everything I already have but adding to it.  It is about resilience and being open to the moment.  It’s about making new friends; taking chances and continuing to learn…and giving up control (something I’ve never been very good at).  So, on this note of self-reflection, I will conclude.

During the times I am in Minnesota, I will take a break from blogging, but whenever I return to Minnehaha, for the boat shows and sailing, I’ll be back at the computer.

Thanks for reading this blog.  It has been fun to write and gratifying to hear from those of you that felt it has added interest to your lives.

Take care and more to come….

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Left Nantucket before dawn heading to Newport RI


  1. Jan Browning · August 24, 2017

    I so enjoyed the beautiful pictures and you’re descriptions and points of interest at each stop. The whaling captains sure lived in beautiful homes! Where will you go on your next sailing trip?

  2. Kim Ode · August 24, 2017

    I’ve so enjoyed reading your posts – learning, commiserating, empathizing, envying (and sometimes not so envying!) Your final thoughts are, well, thought-provoking. Thanks for sharing.

    • minnehahasailing · August 25, 2017

      Back at you Kim. I always enjoy reading what you write, learn from (but cannot replicate) your tips and envy who you meet…e.g. Gloria Steinem as well as how well you write. Sometime we really need to connect in person.

      • minnehahasailing · August 25, 2017

        Should have read. I learn from your baking tips and cannot replicate 😊

  3. Barb Koehn · August 25, 2017

    Thank you Deb for bringing us along on your adventures!

    • minnehahasailing · August 25, 2017

      Why Barbie… I’d take you with me anywhere. Ready for this winter?!?!

  4. Let It Be · August 25, 2017

    Deb this is a great post. Very informative. But also congrats on overcoming your hesitation. I’m really glad you are enjoying your new adventures. Enjoy being back on land! We will probably see you at the Annapolis boat show. All the best.

    • minnehahasailing · August 25, 2017

      Thanks Mary Grace. Did you finalize your deal with HH? See you in Annapolis.

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