We spent a month at a slip in Deep River, CT catching up with friends & family, along with our various boat projects.  Then for the past month, we’ve been away for our summer’s New England cruise.

While we were tempted to head back to Maine, we didn’t want to rush thru (so next year!)  As we haven’t even been over to Long Island in a few years, we decided to spend our month more locally.   We planned to start at Provincetown, then back thru the Vineyard, Block & Long Island.  However, the more I researched Provincetown, the less appealing it appeared to visit by boat.  There is one marina there, semi-protected, but very, very expensive (almost $250/night w/power).  Moorings are unprotected (residents get the good ones behind the breakwater) at over $100/night.  We could anchor out, but it would be completely unprotected with over a mile dinghy ride in open water with limited dinghy dock options.  Taking into consideration the long trip (including the Cape Cod Canal), we quickly reconsidered.  Where else?  How about Nantucket?  Perfect – we haven’t been in 15 years, with Benj in our old Sea Ray.

Being New England, you can’t just go to Nantucket – you need reservations.  A slip was only a bit less than Provincetown, but they have a large, protected mooring field.  So with a week to go before our reservation, we headed off.  Some stormy weather was to begin our trip, but we wanted to at least get started, so we jumped over to Point Judith Pond we’d stopped at once before which was, well, as calm as a pond.

No trip out this way is complete without the required stop at Cuttyhunk.  A magical place!

We have stopped here many times, with 3 or 4 of our boats over the years.  We always walk-the-walk to the top of the island for this great aerial view.  The highlight is always fresh Cuttyhunk oysters right off the boat.  Cuttyhunk was recently in national news as their very last student graduated from their one-room schoolhouse – officially the smallest school in the U.S.  Their year-round population has dropped to only 25 with no young children, so their school is closing after almost 150 years.

Menemsha, near the western end of Martha Vineyard, was our next stop.  We anchored off the beach which is famous for their sunsets.  Every night on the adjacent beach, hundreds of people descend to watch the sun set, with appropriate applauding & cheering.  Years ago there was a sailing catamaran which did a sunset cruise every night with a bagpiper playing on the bow as it sailed in – very memorable.

Edgartown, near the eastern end of Martha Vineyard, was another must-do stop.  While there is much to do & see there, we had to include a bus trip down island to Oak Bluffs for – you guessed it – donuts! Back Door Donuts began, as the story goes, when locals in-the-know would show up at night at the back door of the bakery & knock until the baker opened up to slip them a donut or two.  You still walk up to the back door, but now there is a long, snaking line with up to a hundred people patiently waiting for fresh, hot donuts, ideally eaten right there.  Two years ago they even re-named the bakery to simply – Back Door Donuts.

Weather & fog (lack of) nicely cooperated for our scheduled arrival to Nantucket.  After 15 years, all looked the same, well … except these weren’t here!  The boats (yachts!) have gotten much larger.  They can’t even fit at the docks anymore – these are “med moored” – they maneuver up, drop their massive anchors, then carefully back-in between the other yachts to a dock at their stern.  Of course, the captain isn’t in the pilothouse spinning the wheel & hastily gunning the throttles – no he (or she) simply stands on an open side bridge with a handheld joystick controller calmly operating the engines, bow & stern thrusters to slip right in without any (expensive) drama.

Nantucket is very expensive, so we only enjoyed one meal out, but it was fantastic, up on a deck overlooking the harbor.  If you like to people watch – this is the place.  All of the elites in their expensive clothing spending hundreds in the expensive stores. This might be the only stop where Lori didn’t buy a single thing!  We spent one day touring the island by bus with a stop at the Nantucket Shipwreck & Lifesaving Museum.  It was slightly larger & improved since our last visit.  We received a private tour which was very educational.  As many times as we’ve read about, looked at paintings & seen old photos of rescues of wrecked sailing ships during the 1800’s, it is still unbelievable.  How anyone was ever saved and how any of the rescuers ever made it back alive is beyond me.  It was especially a miracle in places such as Nantucket as the reefs were mostly miles off the coast & the winters particularly stormy.  Let’s say you were wrecked on a reef 3 miles out.  You could try starting a smokey fire to attract attention or at night they would hoist a burning mattress up the rigging (maybe not too successful in stormy, 50 knot weather).  If anyone on the island saw you, a volunteer crew (early on – later paid – the early beginning of the Lifesaving Service – later to become the Coast Guard) would attempt to launch their rescue “rowboat” from the beach thru the huge surf to begin their 3 mile row out to your stricken ship – if they could even find it.  That was the easy part.  To come alongside of a sinking ship during these conditions was nearly impossible – much less remain alongside while attempting to bring a few lucky crew aboard.  There was a dramatic painting of such a situation.  A line had been thrown between boats, with the stricken crew (too) frantically pulling hard on the line, while a member of the rescue crew stood with a hatchet up in the air ready to cut the line.  The French crew quickly understood & were eventually  saved, although the row back wasn’t any easier.  Did I mention there are also strong currents in these waters?  Sometimes they would row for hours, just to remain in place, waiting for the current to change.

On our return from Nantucket, we stopped back to the Vineyard, this time to Lake Tashmoo, to visit with some friends, then onward to Block Island.  Block is always a favorite, but more & more popular every year. We hoped that stopping by on a Tuesday mid-morning we would have a good chance of picking up a town mooring, or at least the anchoring field wouldn’t be too busy.  Wrong on both counts!  The moorings were all taken & we struggled a bit to find a good anchoring spot.  Fortunately our little powercat only needs 3′ of water so can almost beach her. This chart shows we almost did, but in reality we had over 4′ at low tide.  It was a little disconcerting though when I noticed a man walking thru the water past our boat!

We enjoy exploring & eating on Block, but wait … donuts … again!  Killer Donuts are pretty famous here & really good!  They’ve been on Block since 1963 & their slogan is “Worth the Weight”.  Only 3 varieties – plain, sugared or cinnamon/sugar.  We think their secret is sour creme, but Lori says more research is required!

Stopping at Montauk, Long Island was on my bucket list, as I hadn’t been there since about 10 years old.  Rather than stopping at an expensive marina, we saw we could just anchor further in.  We were foiled though, as there is absolutely no (legal) place to bring your dinghy near Montauk Harbor, so we had to pay over $30 just to tie up our dinghy for 3 hours in order to explore & have lunch.  The next day we brought our dinghy to a nearby beachy area near the main road & hailed an Uber ride to Montauk (the town) 2 miles away.  There happened to be a high-end bakery called the Montauk Bake Shop.  Famous for their jelly-filled donuts (not our favorite), we found a few fantastic donuts & pastries – really different & delicious!

By accident, walking back from a small grocery store attempting to get an Uber ride back, we stopped in front of a storefront for shade to use my phone – what is this place – Round Swamp Farm??  Ahhh … if you have $$$$, want convenience & to eat healthy … this is the place!  All sorts of gourmet food & lots & lots of healthy, prepared salads.  We bought & loved their Mexican Sweet Corn Salad!

Continuing back along Long Island, we anchored in Coecles Harbor, part of Shelter Island.  I spent dozens of weekends here in my youth as it was one of my parent’s favorite spots.  Next, we rented a mooring in Dering Harbor, around the other side of Shelter Island.  After exploring the very small town there, we enjoyed lunch at a small restaurant at The Chequit Inn.  The next day we took the short ferry ride over to Greenport to visit some old haunts, including lunch at Claudio’s Restaurant.  Claudio’s was established back in 1845 & was famous during Prohibition for having a secret trapdoor under the bar which allowed small boats underneath to bring up bootleg liquor.

Our last Long Island stop was Sag Harbor, another favorite, in the high-end “The Hamptons”. By accident(?) we came across a former ice cream shop – now a donut shop.  Probably our most expensive donuts ever.  They were good, but not great.  At least our lunch at Dockside did not disappoint.  Yet another restaurant I enjoyed as a youngin’ which is still there & very successful.

By Sag Harbor it was time to do laundry once again.  We discovered we were truly in “The Hamptons” when we went to the laundromat & discovered that the large washing machines were … $9.75/load!!

Back over to Connecticut.  While we’ve stayed at various Mystic marinas over the years (including at the Mystic Seaport itself when Benj was about 8 – Benj & his friend Leonard roamed the Seaport after closing, having fun evading the security guards!), I was intrigued by a possible anchorage just past the Mystic Seaport.  The Mystic River pretty much fizzles out past the Seaport, but there is a tiny area for shallow draft boats to anchor – otherwise only 1′ of water at low tide.  Being a weekday towards the end of summer, we figured we would give it a try.  It was a little weird going thru the famous Mystic River bridge with dozens of tourists taking our picture.  We continued past the Seaport & sounded the bottom looking for a good spot, although a trawler was right where we would have chosen.  After some careful checking, we anchored, only to see the trawler leave 10 minutes later.  Oh well, we picked up our anchor & moved to their perfect spot.  It was a wonderfully peaceful, with the Seaport just off our bow, complete with entertainment.  When the wind suddenly became gusty one afternoon, several of the little sailing dinghies from the Seaport flipped over & their chase boats were busy for quite a while picking everyone up & towing the boats in.

If anyone is looking for the Mayflower replica from Plymouth, MA, it is here at the Seaport for a 3-year restoration, being launched in September.

Our daily dinghy rides took us right past the Seaport, so we couldn’t help from taking a selfie at the stern of the Charles W. Morgan.  I was aboard her many times as a child (back then, she wasn’t even floating – just sitting on a bed of rocks).  After her full restoration, we cruised alongside her when she was “sailing” down Buzzards Bay back in 2014 – quite the transformation from a wreck on the rocks to fully operational & able to sail.  For those not in the know, the Charles W. Morgan is the last remaining wooden whaleship in the world, having been first launched in 1841.  To be honest, there is supposedly only one small piece of original wood remaining, but after 178 years, what would you expect?!

We enjoyed several fine meals in Mystic at favorites including the S & P Oyster Restaurant, the Oyster Club & Sift Bake Shop.  While Sift may not be officially a restaurant, it has recently doubled in size, added a huge rooftop patio & it’s owner, Adam Young, just won as Food Network’s “Best Baker in America”, so we’ll call it a must-go-to restaurant!  Their deserts & pastries are unbelievably good!

It was a great month cruising around “home” waters.  After a Labor Day weekend driving trip up to Vermont to see Benj for his birthday, we’ll be getting ready to soon head south once again.