Cruising Maine: Gloucester to York Harbor

Grit your teeth and get out of Gloucester

Our plan to leave Gloucester and head north to Maine led to an difference of opinion as to which route to take. Going up the Annisquam River is the easier option, but only on the right tide. The other option – sail around Cape Ann, which I was nervous about because:

  1. This would be our first time in the open Atlantic ocean, i.e. outside Massachusetts Bay
  2. The fuel gauge appeared not to be working
  3. Forecast light winds meant we’d mostly be motoring and hence need fuel
  4. The shore out there is rocky and waves would push a boat without fuel and without wind toward shore
  5. Our cruising guide said there was no fuel at Rockport, the only port on the outside edge of the cape
  6. Thunderstorms filled the forecast (we now know that tstorms are almost always in the forecast in July)

As we hadn’t yet instituted good cruising habits such as stowing everything the night before, checking tide tables, and paying attention to the clock,* the morning of our intended leaving we ended up missing the tide. So, in reality we had one choice. Go around Cape Ann.

Fuelish Fears

And for that I wanted to know how much fuel we had. Since my math and the physical evidence were conflicting and inconclusive, I insisted we top off the tank before heading out to sea.

Tom rolled his eyes, but relented and we motored over to the fuel docks. Closed. Not too surprising at 7:00 AM on Sunday, Independence Day weekend. I searched using my phone, and used Tom’s to call all the numbers to find out what time they opened. All were either closed on Sunday or said nothing about their hours. I left a couple of messages.

So, I faced a choice – sit in Gloucester for another day, or swallow my worries. Thinking hard about the evidence, I accepted the idea that we still had some fuel left in that hollow sounding tank. Our little 18 horse Yanmar sips fuel. We headed out of Gloucester Harbor and east.

Cape Ann Lighthouses

There was no wind for the first leg out and around the Cape Ann Light on Thacher Island. As we rounded the island, a little breeze teased us and we put up sails. The sea was glassy and giant rollers lifted us and dropped us maybe three feet, but they were so wide that the motion was almost undetectable.

We easily made it around Cape Ann and set a new course for the Isles of Shoals. One of the most famous of these is Appledore Island, where Celia Thaxter grew her garden and Childe Hassam painted it. Another is Smuttynose, famous for a notorious murder and a kooky name, which now graces the Smuttynose brewery and line of beers.

Sometimes there a breath of wind let us sailed for a bit, but most of the time we motored across a glassy expanse of sea known as the Scantum Basin.

bow wave

(Tom took this picture)

Fog scare number one

fog at sea

Just short of the islands, we encountered a fog bank, but it was light and short lived. Once we had the islands in sight we re-set a new course for Portsmouth, New Hampshire.

Past the islands, with the outline of the mainland visible, we found ourselves in a breeze and sailed a little north of Portsmouth, just for a change of pace. Then we sailed back south again, dropped sails and headed into Little Harbor, to meet up with Jesse and Stacey and spend the night.

isle of shoals

Jesse and Stacey had taken a slip at Wentworth by the Sea marina but we, on our shoestring cruising budget, were intent on trying to pick up a mooring. The cruising guide informed us that the harbor was full of state owned moorings that were leased for the season, that at any one time there were likely to be half a dozen unused moorings, and that it was the done thing for transient vessels to borrow these moorings for the night. The one caveat being that, should the lease holder return in the middle of the night we’d need to be prepared to surrender the mooring. (We’ve since learned from a local that the moorings are actually private, but the fair use policy still prevails.)

Goldilocks at Sea

And so we started the search for the perfect mooring.

The first we tried had no pennant, was not maintained, and the line appeared to be too light for Sunshine. Too small.

Mooring number two we approached too fast, I grabbed it but couldn’t hold the hook, and then couldn’t get it loose of the buoy. The hook pulled out of my hand. Tom shoved the engine into neutral and dived overboard. He was afraid we’d lose the hook, but really, we could have just gone around again and retrieved it, it floats, and besides, stuck as it was it wasn’t going anywhere. Maybe he just wanted to cool off, it was a hot afternoon. Too embarrassing.

after hook rescue

Mooring three lay ahead and I easily grabbed it. This one belonged to the Portsmouth Yacht Club, and we awaited the launch to charge us or kick us off. In the end we kicked ourselves off. The boat seemed to be caught in a current and rocked and rolled while the boats around us sat still. Too bouncy.

The fourth buoy we chose was further out in the field, I nabbed it successfully and once tied off we found it much more stable. Just right.

Portsmouth, New Hampshire

Sunshine Little Harbor Fog

We spent a comfortable night and didn’t get rousted out. Early in the morning I found fog had settled in and went out for a row to take pictures of Sunshine in the fog. After showering, I rowed us to the marina where we met Jesse and Stacey for coffee. While we were ashore the wind came up.

Since I’d been intent on rowing, I’d convinced Tom we didn’t need the motor to go so short a distance. Oops, now faced rowing back against the wind and current. It was hard going. To save his arms, we hopped from moored boat to moored boat. I grabbed hold of them and held on so he could rest. One, a Freedom 30, we circled hand over hand, checking out her rigging and equipment for ideas.

Tom’s strong and we made it back to Sunshine just fine, but the oarlocks took more strain than they’re designed for and are now slightly bent, so we can’t take the chance of getting in that situation again.

Jesse and Stacey changed their plans due to the weather. They’d wanted to make it to Kennebunkport but with their vacation time running out, they settled on a short hop to the tiny historic town of York Harbor, Maine as soon as the weather broke. We would tag along with them, and when they headed back south from we’d try taking another hop north and get our first taste of cruising entirely on our own.

The next morning we did some laundry and grocery shopping and poked around in Portsmouth, a charming old town with many 17th century buildings. Shops displayed things I’d not seen before – dishes made from chunks of salt that look more like marble than a condiment, vests and handbags like silky chain mail that might have been made in Rivendell. (On closer inspection they’re cleverly made from discarded soda can pop tops crocheted together with almost invisible threads.) A gallery was full of fanciful – but far from kitschy – finned creatures in sizes from Christmas tree decoration to mammoth wall made from found materials and wildly painted. The Portsmouth Brewery was worth a stop too. While the others enjoyed sampling and critiquing flights of the various beers, I took in the architecture and interior décor, notably the stall doors in the bathrooms, which are pieces of old brewing tanks.

Finally – Cruising Maine, York Harbor

Though the weather was still blustery and gray, we headed out of Little Harbor the next morning, motoring fast for York Harbor. We left first, but before long Smitty, with her 26 horse engine, blew past Sunshine and we trailed them into the zig-zag entry to York Harbor.

smitty passing sunshine
terns and lobstermen

We spent three nights in York, enjoying the laid back surroundings of serious lobster boats, balls-to-the-wall kids from the very friendly Agamenticus Yacht Club learning to sail, and terns fishing for herring. The town of York, a short walk up the hill featured a looping route that took us past a great bagels and coffee spot, the oldest jail in the country, a likewise ancient cemetery and down to John Hancock’s wharf. Beside the wharf an old store building is now a gallery.

Walking toward it, I spied part of a huge wooden wheel in the window up under the rafters. While wandering the gallery viewing art pieces inspired by the 50th anniversary of the publication of Rachel Carson’s Silent Spring I asked about the wheel. And just like that we got a tour of the inner workings of the old store. The wheel was the still intact hoist used to lift provisions up and down for storage or delivery.

york gaol
york cemetery
hancock's wharf
wheel in window
york wiggly bridge

After we finished at the gallery, a nice walk in the woods led down to the wiggly bridge that crosses the mouth of the old mill pond and on to the pub on the cliff top that replicates below decks on a schooner. That’s where I discovered the Strawberry Basil Smash I’ve been thirsting for ever since.

Image of drink and plate of food

On the way, Tom got a call that scared him, and the look on his face and the things he said scared the rest of us. A mother told him that she’d found his phone number in her underage daughter’s phone. She wanted to know why her daughter was calling strange men. Heck, I wanted to know why her daughter was calling Tom. Jesse and Stacey were just fascinated by the whole drama.

It took a few minutes, but we sorted out the events. I used his phone to call the gas dock in Gloucester. The daughter used her phone to return the calls she found on the business answering machine. Tom received a strange message that he couldn’t figure out and deleted it. In the end his explanation satisfied the woman that he wasn’t messing with jail bait. He barred me from using his phone.

Parting Ways

smitty leaves york

Jesse and Stacey tried to leave us the next morning, but after making it out the mouth of the harbor they turned back because of the fog. When they did leave the morning after , we were sorry to see them go. For one thing, because they’d wanted to make it further into Maine. For another, becaus togetherness as a kind of security blanket. We would now have to make our way into the wilds of Maine all by ourselves.

Which is probably why we instead decided to walk the six mile round-trip to Cape Neddick. Caught by a squall, we got back too late to get fuel. A Freudian walk as it were. We stayed another night in York.

york sea walk
cape neddick
cape neddick squall

First re-fueling: The moment of truth

And we missed the tide again. The low tide depth at the fuel dock in this little harbor wasn’t quite enough for Sunshine’s keel so we waited for the incoming tide to head over to the fuel dock. When Tom finally pumped that diesel into the twenty gallon tank it took only nine gallons. We’d used less than half a tank since December! All that worry for nothing.

Image of sailboat at fuel dock filling fuel tank. Cruising Maine, York Harbor.

And then, with no excuses left, we had to do it. We pulled away from the dock and started cruising – just us and the deep blue sea.

off to Maine

* Full disclosure – after two months cruising we still haven’t managed this.

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  1. At last the never ending story has resumed! Great stuff my dears! Love all the tidbits collected in the nooks and crannies of shore time excursions. I am puzzled though by the red asterisk and how it fits the story. Continue the tour and the Log of Sunshine with our blessings when back from your vacation to Montana for young Thomas’s arrival. Would it perhaps be necessary to provide friend Jessie with the term ‘Whidbeyians’ or even ‘Freelanders’ as more descriptive than ‘Seattleites’ to describe what Island Time is all about? That conversation must be worth at least of cracking a bottle of Rhubarb wine!

    Old Roy

    1. Yes, finally, and don’t hold your breath, but another installment is coming in a day or two, just as soon as I locate a few more pictures.

      The asterisk leads to a little footnote at the bottom of the page, it refers to the fact that we still haven’t got a clue how to organize ourselves the night before so as to get an early start.

      I’m okay with the Seattleite designation. The correct term Whidbey Islanders is way too boring, and Freelanders makes us sound like Tea Party members. As our home is now this boat I guess we’re Sunshiners. I hope there’s no derogatory connotation to go with that.

      1. Ok Sunshine-ers works! Or perhaps a nick name ‘Shiners’? Glad she is not lunar titled as that could keep you out of some harbors! LOL

        May the wind be always at your backs!


  2. I can’t believe the cruisers from Seattle didn’t mention the Common Ground coffee shop. You are just throwing all of my stereo types of Seattlians (?) out the window.

    Glad to be part of it. Hope you find your substitute for the Strawberry Basil Smash soon.

    Fair winds,


    1. What I remember from Common Ground wasn’t the coffee, I’d had my quota for the day. But those pastries! I had a really hard time not spending the rest of our budget for the month on those.

      And the correct term for Seattle natives is Seattelites, because we’re all a bit spacey.

      We’re back in Boston and looking forward to sailing with Smitty and crew again.

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