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While it’s not necessarily bikinis and beach towels, the islands in New England offer their own unique charm.  Phillip and I have had an exceptionally difficult time deciding which port(s) in the New England cruising grounds were our favorite. They’re all so lovely.  While Block Island—our first island in NE—struck us, we later thought its “firstness” may have had more of an impact than we realized, when we finally got to experience other islands like cordial little Cuttyhunk and memorable Martha’s Vineyard.  Join us, on our first exploration through these exquisite little NE islands.

July 2022

After our endearing experience watching the nation’s longest-running Fourth of July parade with our entertaining friend Bridgett in Bristol, RI, we sailed across Narragansett Bay to Greenwich Bay and explored Warwick, RI (always makes me think of Dionne Warwick and the Psychic Friends Network … couldn’t help it) as well as Greenwich, RI.  Then it was back down to Newport to stock the boat back up for the next couple of weeks which we planned to spend checking out the first of the Elizabethan Islands, Cuttyhunk, and then the coveted Martha’s Vineyard—a place I honestly thought I would never go in my life!  It always sounded so fancy!  And, to tell you the truth, for half my younger years I literally thought it was just a vineyard owned by Martha Stewart.  Not kidding.  It’s a good thing Phillip plucked this little country girl out of Alabama and opened my eyes to this great big world.  

I don’t think Phillip or me will soon forget our sail from Newport to Cuttyhunk.  The boats that fly in and out of the Newport harbor are simply mesmerizing.  All shapes and sizes and speeds and styles.  The sailing feels like the breath in and out of that historic port.  When Phillip and I left on a brisk day in July (yes, it can be brisk in NE in July) we found ourselves immersed in a fleet of other boats, all with rails buried, tacking and gybing all around us.  It was exhilarating.  And, Ubi was matching them toe to toe.  It is always so rewarding to be reminded that not only did we purchase one of the most comfortable liveaboard monohulls I could imagine, she’s also just really fun to sail!  Outbound did an exceptional job building our (second) baby girl!

The Cuttyhunk Welcome Committee

I don’t think I’ve ever experienced such a cordial welcome to an anchorage.  Cuttyhunk is the first of the Elizabethan Islands in Massachusetts (and so it served as our introduction to Massachusetts) and just a short day-sail from Newport. Phillip and I didn’t know what to expect when we pulled into the protected little cove that serves as their mooring field. We saw a few mooring balls that seemed to be reserved or off limits, and, otherwise, most of them seemed to be already taken.  As we motored around in search of an available ball, a little John boat came out to us, confirmed we were looking for a ball, and took us straight to one that was available—a relief as it’s not ideal to grab a ball and get secure only to be told immediately afterward that you have to get off and move because you snagged an unavailable ball.  But, the assistance of the friendly folks at Cuttyhunk did not end there.  As soon as Phillip and I got Ubiquitous secure on (what we were now sure) was her ball for the next few nights, that same john boat came back out and tied alongside.  

“Ahoy! We’re the Cuttyhunk Welcome Committee!” he said cheerfully.  “Here are some trash bags for when you bring your trash to shore.  They only pick up on Tuesdays.  We’re having a potluck tonight at the dock if you want to bring something and join.  Rum is always popular.  Oh, and breakfast tomorrow morning as well.  Champagne is quite popular. There’s trivia Monday night, too, and Soprano’s is open now.  Great pizza.  Enjoy our little island.  Hope to see you ashore!”  

Everyone on the “welcome boat” waved and wished us a good evening.  It was incredible.  Phillip and I, and UbiQ, felt so welcome!  I think we were invited to every social event they were hosting that weekend.  And we’d just arrived!  Phillip and I looked around at the other boats in the cove and felt like we’d just settled among friends.  We dinghied ashore the following day to explore and were thrilled to soak in another hydrangea-adorned, breathtaking New England island.  Cuttyhunk offered its own charm in that it is so small.  A local at the museum told me the population can get down to as low as 15 people in winter.  Just 15 people!  They had a little library with a cardboard sign taped up.  A trivia night that—we quickly surmised—was fiercely competitive among regulars.  Just so many little things that charmed us.  We will definitely return.  

But, then, you have to imagine this place in the winter, how those lone 15 people see it.

The fact that these islands can really only be enjoyed by cruisers for a few months out of the year, I feel, makes them all the more special and attractive during the summer months. We enjoyed our weekend at Cuttyhunk, but it was soon time to leave that cozy mooring ball with our sights set on Martha’s Vineyard, a port that had evolved into a coveted destination for us that summer after many (many!) cruisers told us how lovely it was and that it was their favorite New England port.  Challenge accepted.  We had to sail there and experience it ourselves to find out.  

Making Happy, Chappy Memories at Martha’s Vineyard

While each of the New England ports Phillip and I visited last summer brimmed with hydrangeas of every color, Martha’s Vineyard positively overflowed with them.  I couldn’t stop taking photos of these fluffy pastel masterpieces we saw everywhere we went.  They also make incredible backdrops for selfies.  Doesn’t life among hydrangeas just look more enjoyable?  I know I will look forward to seeing and soaking up these exquisite flowers every time we do New England for the summer.  

But, that’s simply the flora and fauna.  Martha’s Vineyard also offered incredible shopping (Phillip and I found some really unique galley pieces and post cards and trinkets to send home to friends and family).  I discovered one of my now favorite photographers at the Untameable Gallery.  

Phillip ate the best cauliflower (yes, cauliflower) Reuben at Rosewater Market.  

Edgartown is filled with exceptional restaurants and bars overlooking the harbor.  

The mooring field on the inside is also rather large and easy to navigate.  But, we anchored on the outside with just as much ease and comfort and the dinghy ride in is quite exciting with the notorious car ferry (featured in JAWS!) going back and forth from Martha’s Vineyard to Chappaquiddick every 5-10 minutes.

Ashore, the streets of Martha’s Vineyard look like scenes straight out of a child’s storybook.  I kept thinking little blonde-headed children were going to walk up to me and introduce themselves as Hansel and Gretel.  

Phillip and I also took the bus one day to the island to spend the day in awe of the multicolored Oak Bluffs and stone-strewn shoreline (that’s a tongue-twister) on the north northeast shore of MV.  We saw a few other things while we were there that I don’t think I’m at liberty to mention on such a public platform …   Those of you who know MV, get it.  In all, it was a wildly fun day for the eyes and a glorious day at the beach, albeit a different kind of beach than we’re used to, but beautiful in its own unique right.  

I believe if I were to ask Phillip, however, he would say he holds the same memory from Martha’s Vineyard as his fondest—our day with Frank.  Phillip and I had run into another boat (this happens frequently when so many cruisers are visiting the same ports all summer), Jamie and Sheryl on Pacific High at Martha’s Vineyard with whom we had buddied up with in Ft. Lauderdale and other ports.  Jamie, Sheryl, and their crew and Phillip and I decided to go out for drinks ashore in Edgartown one evening and we ran into this lovely man, Frank, and his dog at the Behind the Bookstore bar.  Frank is a long-time local of Chappaquiddick and he regaled us all night with tales and stories that brought the history of the island to life which included, naturally, the Ted Kennedy scandal.  Having now seen the distance Ted ran and the channel he swam while that poor woman was drowning in the car he wrecked was heartbreaking and haunting but it did add to the rich allure of both islands.  

Frank’s stories, however, told of island life during the dreary winter months and how the locals that stick around pass the time: “Alcohol and books, more alcohol and firewood.  Don’t burn the books,” Frank said.  He was a hoot.  After a few crazy hours over drinks, the man was crazy enough to invite the five of us to Chappaquiddick the following day where he offered to chauffer us around and provide us with a personal tour of an island he has watched grow and change for forty years.  We did not regret the decision to take him up on it.  It was fascinating to see Chappaquiddick from a local’s perspective, understand the growth and changes, and get some scoop on the sly celebrities that have purchased homes there: Spike Lee, David Letterman, Carly Simon, James Taylor, and Diane Sawyer to name a few.  

Frank ended the tour with drinks and snacks that he served up for us himself at his home there in Chappaquiddick.  Overall, it was such a hospitable tour and a unique memory to take away from the island.  Martha’s Vineyard—and hopefully a reunion gathering with Frank—will be high on our list this coming summer!

Since 1785.  2022 was going to be their 236th straight year running, on the very same street where we were standing.  Do you know what Bristol, RI’s biggest claim to fame is?  The longest-running annual Fourth of July parade.  And, for its 236th year, we were planning to sail from Newport to Bristol to see it.  I was expecting big things.  Elephants.  Ladies juggling swords.  Pyrotechnics.  What we got was a completely different, mesmerizing experience.  And, I wouldn’t have traded it for any sword-juggler in the world.  Come with us, folks, from Newport to Bristol during our cruise in New England this past summer to experience a true Bristol tradition: the longest-running Fourth of July parade in the nation!  

July, 2022: 

While it is very hard to say which port was our favorite in New England.  Noank Village was quaint and genuine.  Block Island has its own charm, and bluffs, and island pride.  Martha’s Vineyard has hydrangeas in every color of the rainbow and exceptional dining and shopping.  But, Newport.  I think the sailing in Newport is what stole our hearts and put it #1 on our New England list.  It is such a historic port where boats have been sailing to, often from across the Atlantic, for hundreds of years.  The many varied sizes, colors, and crafts of boats in the harbor is dazzling.  And, the quaint brick streets, salty taverns, and new additions—like the Sailing Museum, Cliff Walk, the Mansions, and Tennis Hall of Fame—made the place a real gem.  

This doesn’t even mention the popular little beaches where the sight of surfers made my heart leap, and made Phillip jump at the idea of gifting me a lesson for my big Four-Oh!  Story here.  

And, the place was so cruiser-friendly, with a “water barge”—basically an easily accessible floating dock in the harbor—that you could dock up to at any time and fill the tanks, a free dinghy dock behind the Sailing Museum with a great work space there for cruisers as well as bathrooms, showers, laundry, and a book exchange – my favorite!  But, I think our favorite part about Newport was just sitting in the cockpit on the hook watching the dozens of different sailboats go by, from big tall-ships, to pirate-esque sailboat charters, to Bristol fashion craft boats, to little racing dinghies, even mega yachts, and vagabonds.  Everything in between.  The harbor itself can easily be enough entertainment for happy hour.  

Phillip and I love Newport.  I think the only thing that could make it better is … Bridgett!  We invited a good friend of ours up from Pensacola to stay aboard the boat with us for a few days to visit these cool New England ports (and I do say cool because Pensacola in July was in the 90s while Newport was in the 70s, so much more comfortable).  Bridgett has been long-affiliated with HaveWind.  She was the originator and facilitator of our Progressive Boozer Cruiser Back in 2015.  We bonded then, and we’ve been inseparable friends ever since.  

We enjoyed several days strolling around Newport, extending and accepting fun sailing challenges at the Sailing Museum, and enjoying some lovely rooftop “bevies and bites” (Bridgett’s words) with our amazing friend.

We then whisked Bridgett up the Narragansett Bay to Bristol, RI aboard the gallant (and fast!) UbiQ.

Why Bristol? We were not going to miss the nation’s longest-running Fourth of July parade from a lovely little perch that Phillip booked us (something we heard was a long-standing tradition in Bristol): viewing the parade from Linden’s Place.  

As we settled in our chairs with a front-row view of the street, I was astounded at how many people began to line the streets.  On this tiny little island in Narragansett Bay, folks really turned out for this parade.  And, I now know why.  It wasn’t the pyrotechnics, the acrobatics, or any flashy, razzle-dazzle.  It was Mayberry.  Straight-up back to the 1950’s good old wholesome USA Mayberry.  

It was amazing to realize this same parade has been marching down this same street, Hope Street, for over 200 years!

In addition to the traditional “small-town” elements of parades I love: horses (I always hope to see Clydesdales); baton twirlers (I love when they throw them up and spin around), and marching bands (I am a sucker for the drum line), this is a list of just a few of the folks and little “floats” (often carts pulled behind bikes) that I remember marched in the Bristol Fourth of July parade: 

1. The oldest person in town (her banner boasted she was 102!);
2. A guy named “Bob” whom we learned sat on the Board of Commissioners (everybody knew him, some even called out asking about his wife and girls);
3. The local milkman (I’m not kidding, he still delivers bottles to folks’ doors, everybody knew him); 
4. The local postman (everybody knew him); 
5. We then joked we would see next the utility company and water authority (we squealed with delight when we did, everybody knew them);
6. Bristol’s elementary school spelling bee winner that year; and
7. This cute little 2nd grader who had won the art contest for Bristol’s 2021 “town button” (in Bristol they still wear buttons).

The whole thing felt so local.  It was beyond charming.  We had the great fortune to sit next to a long-time resident of Bristol who educated us on each person and float in the parade.  It was fascinating to see this microcosm throwback to times when everyone in town knew everyone.  Phillip, Bridgett, and I left the parade feeling uplifted and giddy.  It’s tough for me to recall a Fourth of July parade I have ever enjoyed quite so much.  I hope Phillip and I find ourselves back there in July of this year to experience it all again.  

After the parade we strolled ourselves over to the Thames Waterside Bar & Grill (pro tip: live music always helps to steer us in your direction) and spent an absolute hilarious and entertaining few hours hanging out with a flock of Navy guys on leave at the bar as well as a handful of other colorful characters, Joey from Boston who invited us to his restaurant if we ever we sail through Boston, an English teacher named Dan who invited us to come hear his band play if we ever sailed into Greenwich (on the other side of the Narragansett Bay).  It was just an incredibly memorable day.  Bridgett always plays a heavy hand in an experience like that.  She’s like the flame every moth in the room is attracted to.  Bridgett, we had such an incredible time hosting you aboard UbiQ!  We hope you’ll come visit us again soon!

And, of course, no Fourth of July should ever end without fireworks. Back aboard Ubi anchored near Bristol in the Narragansett Bay, Bridgett, Phillip and I were treated to fireworks from every direction. I finally got those pyrotechnics I’d been craving.  360 degrees! Wherever you looked, lights were bursting like popcorn on the horizon. It was a real treat!

And, folks, if you ever find yourselves in the Narragansett Bay around the Fourth of July, you now know where to go and what to do!  Next up on our New England, we’ll continue our travels to the quirky little island of Cuttyhunk, and the regal, storied Martha’s Vineyard.  Stay tuned! 

Not a surfer was stirring, not even those serious about the sport.

My wetsuit was hung in the cockpit with care, in hopes that in the morning a hot instructor would be there. 

My 39-year-old brain was nestled snug in our vberth with visions of what me at 40 would look like on this Earth.

With Phillip’s promise of a birthday surf lesson on my mind, I closed my eyes to leave my 39th year behind.

Phillip’s scrambling the next morning woke me with a clatter: “Get up, it’s time to go!”  “What bikini?”  “It doesn’t matter!” 

For the water in Newport in summer was a brisk 65, but with a wetsuit it made you feel fresh and alive. 

We topped the hill on Memorial Boulevard and to my eyes did appear, the little crook of Easton beach with lapping waves I could hear.

A slick long board was brought to me nice and quick by my “tasty waves” instructor whose name was Nick.

After a few practice pop-ups on the beach, Nick took me to the water where there was a lovely swell, 1-2 foot each.

On my tummy the rise of each wave felt strange and new as Nick pointed me to shore and, shouting, told me what to do.

“When I tell you to paddle, dig hard, don’t give up.”  “Now PADDLE, now PADDLE, DOUBLE PADDLE and POP-UP!”

And just like that, to my utter disbelief and surprise, my body was propelled in a way and by forces I could never surmise.

I did it, I thought.  I surfed a wave.  Popped up from my belly.  I could see Phillip ashore looking astonished and (I hoped) a little jelly.

As I coasted to shore and his joyous face came into sight, Phillip shouted: 

“HAPPY BIRTHDAY TO YOU, ANNIE.  YOU SURFED WITH ALL YOUR MIGHT!”

So … this is 40.  Not too shabby I’ll say.  

This impromptu surf lesson from Phillip was the perfect gift to celebrate my big day.  While we kite-surf a ton and I’ve “surfed” plenty of waves that way, I’d never “popped up” and truly dropped into a wave.  It was mesmerizing, thrilling, seemingly miraculous.  My brain could not convince my arms, right before each pop-up, that it was going to work, and then you just have a little faith and jump up and (most times) there you are, suddenly surfing.  I will relish any chance to surf, in the traditional way, like this again.  What an incredible feeling!  We are also looking forward to sharing more of Newport (then Bristol, RI for the Fourth of July!) with you all here on the blog.  (But I love the tradition of writing a unique ‘Twas the Night Before’ piece here each Christmas (2017 and 2020); I hope you enjoyed this one).  Phillip and I wish you all a wonderful holiday.  We’ll see you here next year (2023, can you believe we made it?) to continue sharing our first summer in New England!  Stay tuned!  And, happy new year!

It’s hard for me to find words that capture the feel of New England.  Mossy stone fences?  Steep grassy hillsides?  Squiggly boat reflections in the water?  Fleeces in July?  Raw oysters and rosé?  It’s tough to say, exactly, but it was this cool feeling in our lungs that told us “We’re not in Florida anymore.”  In May/June of this year, Phillip and I sailed back up through the Chesapeake and into the Long Island Sound to spend our first summer in New England.  We had heard of many cruisers who do this every year—sail north to Rhode Island, Maine, Massachusetts, etc. to get out of the hot temps and hurricane box during hurricane season and then sail back down the east coast in the fall to enjoy the tropical temps and Bahamian/Caribbean islands in the winter.  Like snowbirds, in a way.  Call them sailbirds. 

Since work obligations and travel restrictions kept us in (or close to) the States last winter, Phillip and I decided to find out what these sailbirds knew that it seemed we didn’t.  In April, Phillip and I decided to point Ubi north to the Long Island Sound to sail around New England for the summer.  What did we find?  The ports were cool, accommodating, most only an easy (and fun) day sail away.  The experience was vastly different than all the cruising we had done before in the States.  Phillip and I soon became staunch fans of summering in New England.  Have you ever done it?  Wonder what it’s like?  Come with us, and experience what we felt was our first true taste of New England: Block Island, RI.

Our sail back up the east coast found us stopping in many of the same ports we did on the way down in the fall of 2021: South Beach, Miami, St. Augustine, Charleston, SC, Hampton, VA.  We then sailed back up the Chesapeake to Annapolis, MD and took the C&D (Connecticut and Delaware) Canal headed to New York. 

Some fun highlights along the way:

• Having Chris and Megan, our adventurous Pensacola friends who purchased our 1985 Niagara 35, fly in and join us for a sporty passage (their first overnight) from Miami to St. Aug in April.  Megan and Chris did great on passage and—very cool—found it so inspiring they set off on their first overnight in the Niagara this past October.  We’re really proud of these two!

• Hosting our equally amazing Pensacola friends, Stephen and Beth, on UbiQ for a few days in St. Augustine (the second oldest city in the United States after Pensacola … Pensacola people know what I’m talking about), but a very fun “ancient city” to pilfer.

• Celebrating my big FOUR-OH on May 28th with a “passage feet” selfie in Solomon’s Island making our way back up the Chesapeake toward Ubi’s home port of Annapolis.

• Catching up in Hampton, VA with these two incredible cruisers, Spandana and Dev, whom we cruised around the Abacos with in December of 2021. Spandana and Dev had quite a rollercoaster of a year, but they are back in the swing of cruising and sharing their eclectic stories at For Sun and Stars on Youtube. Check them out!

• Enjoying a visit with Ubi’s former owner, Jim, and his partner, Ann, in Annapolis and enlisting his invaluable help putting a new set of lithium batteries (540 Ah) in the boat.

• Traversing the C&D (Connecticut and Delaware) canal for the first time on our way toward New York City with a thick shelf cloud threatening to drench and toss us that, thankfully, just ended with a little drizzle and a glorious rainbow.  Whew!

• Sailing around in the New York Harbor by the Statue of Liberty for the first time with the grand skyline of NYC in the background.  We anchored behind Ellis Island to enjoy the view of the Big Apple from Ubi at night before making our way with the tide through Hell’s Gate the following day headed toward Port Washington, NY for our first foray into the Long Island Sound and New England for the summer.

Port Washington, NY

It would be difficult to put the feeling of the Long Island Sound into words, to explain why it felt so different than the hot salty waters of Florida and the Bahamas.  Phillip and I have cruised plenty of islands, strolled crystal white beaches, baked in the sun and salt, but Port Washington felt new.  The reflections on the water were clearer.  The morning fog thicker.  The short cruising season (before the ice of winter sets in) making the “summer window” seem more savored.  The ancient lighthouses and stone fences.  The quaint little village feel of the city.  Everything about the place told us this summer was going to be a new experience.  And, what we found we really loved about Port Washington was not only the beauty but the convenience.  A mooring ball that was only $45/night and came with a free water taxi most business hours of every day.  Great shopping downtown and a diverse range of excellent restaurants (La P’Tite Framboise (the “little raspberry”) for French, Nikkei for Peruvian, Diwan for Indian).  The dinghy dock located right across from the Stop ‘n Shop for groceries and just a short walk from the laundromat, the wine/liquor store, UPS, Walgreens, Ace Hardware, Target, etc.  Not to mention (I mean … holy cow) Port Washington is just a short, $10, 40-minute train ride on the LIRR then you’re in Penn Station, with a full day in NYC to explore (while only paying $45/night for NY lodging)?!  We rode the wheels off the LIRR.  Why wouldn’t you?  NYC, right there! 

We stayed 4-5 days in Port Washington getting some office hours in, provisioning up, and enjoying the big city before bumping back and forth across the Long Island Sound to our next extended stop in Noank Village, CT.

Noank Village and Mystic, CT

Noank had the same New England charm that Port Washington did, but it was like the amplifier was turned up.  It is a small village so there aren’t near as many shops and restaurants, but that’s what made it feel that much more intimate—the cladded houses, steep drives, rolling lawns.  The kaleidoscope of boats in the harbor.  We grabbed a ball from the Noank Village Boatyard that, too, came with a launch.  We started to notice many New England cruisers don’t carry or commission their dinghy when they come into a harbor.  They just grab a ball and call the launch.  There is an elegance and ease to that.  A great opportunity to dawn your best boat dress and wedges for a fancy dinner ashore.  In Noank, I also got to know this incredible life-long sail maker, Katie Bradford with Custom Marine Canvas, while we were there.  Katie launched her marine canvas business in Noank in 1985 in an unheated warehouse ( … in Connecticut?!) with only one employee, her cousin, and she’s been killing it ever since.  Katie was a hoot.  Just a real Noank character.  I love when you get to know a place like that.  We also enjoyed eating at Ford’s Lobsters looking out over the harbor.  And, Mystic, CT, was just a short and very cool dinghy ride away (through an old swing bridge).  The incredible marine history at the Seaport Museum was a real treat.  If you do, do not (do not!) miss a dinner at Bravo Bravo.

Block Island, RI

Phillip and I have been struggling all fall to decide which of the New England islands and ports were our favorite (a very tough problem to endure).  Newport is exceptional, and likely our top choice.  But, there’s Martha’s Vineyard.  Cuttyhunk.  Bristol.  It’s really a tough call.  And, for me—at least until we got to Newport—Block Island was my favorite.  And it may still be.  It was our first island, and maybe that’s what did it.  And, it is an island in the Atlantic Ocean.  That offered its own extra element of magic.  The hilly terrain, sprawling lawns, and charming lighthouse captivated us as well.  The monochromatic bluffs and river-stoned beach took your mind to another place.  We biked the entire island and loved the challenge of the rising hills and thrills of the drops.  Drinks and snacks at The Inn at Spring House was a real treat.  Made me feel kind of like someone who could say “We summer in the Hamptons.”  It was surreal.   But, that’s just the fun and elegance.  Block Island is also just a short day-sail away from Montauk and Sag Harbor to the west, Naragansett Bay to the north, and Martha’s Vineyard to the east.  It also offers an easy inlet and nice large harbor for cruisers, convenient access to the dinghy dock, the entire island is walkable with a great fish market (Dick’s) and lots of quirky shops (home décor, books, trinkets, toys).