Month: August 2026

Isle of Shoals, Salem

So, now two weeks later, it’s time for me to wrap this thing (blog posts) up.

I left Kennebunkport at around 8 am, a record in earliness for me. Of course, I got stuck in the mud on the way out (it was low tide). A passing boat pulled me off and away we went.

I wasn’t sure how far I would go. I could go all the way home (12 hours) or stop at Isle of Shoals (~5 hours). I decided to decide when I got there.

Again, due to the prevailing wind, I was motoring, with some motor sailing at times. It was a slog. I decided to stop at Isle of Shoals. I had stopped here on the way up. If you’ve never been there, you should go, it is an interesting, beautiful spot.

I picked up a free mooring, put up the awning and had lunch in the cockpit. At some point later (maybe I was napping?) another boat pulled in and took the mooring in front of mine.

This was a true voyaging sailboat – made of steel, the decks loaded with stuff. There was a platform welded to the back, a dinghy mounted on davits, with a solarpanel above it. There was nothing elegant about any of it, but at the same time, the owners, a young family, were out there doing the thing, crossing oceans.

Hopen of Sweden

After a quiet night at Isle of Shoals, it was time for the last leg. Again, winds out of the south meant not much sailing, but occasionally I would turn west and get some motor-sailing in at least.

Rounding Cape Ann I had a bit of weird moment. There was a small rocky island near me, and off in the distance Thacher Island. It was hazy though, so thatcher had a mirage-like quality to it. It was surreal. I knew where I was (duh, Cape Ann) but when was I? It was easy to imagine I was deep in the past. It looked like this – 

Not Christopher Nolan’s Odyssey

Those two pillars are, of course, the dual lighthouses on Thacher Island. They are much less interesting when they are nearer – 

Anyway. The rest of the day was fine, no more time travel. I tied up to our home mooring around two in the afternoon. 

I will probably do this trip again, hopefully make it farther north, as Maine sailing is supposed to get better the farther north you go. I will add an autopilot and a dedicated navigation system though. Hand-steering while manipulating an I-device is no good, especially single-handed.

Kennebunkport

So, I departed Diamond Cove late-morning, planning to get to Kennebunkport or Wells. This was one of those return-from-Maine days. Winds from the South West. No good for sailing. Or at least not if you are looking at the return trip as a delivery, as I was, rather than as part of the trip.

I motored up the narrow Kennebunk River to where I thought be staying for night, only to learn that it was full. I called another place on the river and they had one spot left, but not for another hour. So I went back out in to Saco Bay to goof around while I waited. I had to be in by 4:30, as I had a job interview call at 5.

That all went well. I ended up tied to the fuel dock between several million dollars of power boats. I went into town for dinner and to grab some odds and ends. Kennebunkport is weird. The security zone outside the Bush vacation home is still there –

Diamond Cove

So, the day after finding my piece of Maine granite, I did some boring shore stuff. Laundry, etc. Then motor-sailed to southern corner of Casco Bay. I wanted to start moving in the direction of home and Monday was predicted to be a complete rain-out. On Sunday afternoon, I ended up in Diamond Cove. 

Diamond Cove is a neat place, a former US military site, now remade into an island destination for Portlanders. 

The rain Monday arrived and rain it did. Inch and a half, I think. Left the dinghy with three inches of water in it. I spent the day trying to install the autopilot, which I had been carrying with me in a box. I failed.

There is a piece of old hardware in the way and I couldn’t remove it. Stainless screws, aluminum part – basically they are chemically welded at this point. Usually, you use lanolin to prevent this – yes, sheep grease – but who knows how old this fitting is or what was used to mount it. I also did a couple hours of cleaning. Progress.

I had a hard time sleeping, but I did get this early morning picture as a consolation-prize:

Sunrise, Diamond Cove (4:30 AM!).

Quahog Bay

And so, I did. I put us, me and the boat, on a granite ledge for about ½ an hour. This is not uncommon in Maine but still terrible. Luckily no damage to the boat or to me. I was helped by Andy in his kayak and a power boat that stopped by. They took my main halyard, which goes up to the top of the mast, and pulled Holiday on her side until we floated off. Phew.

A good look at Maine’s granite ledges – and the boat-ledge interface.

It was my fault. I was looking at a possible anchoring spot when it happened. I had turned the boat away from the ledge but didn’t turn far enough. Sailing adage – “Anyone who says they’ve never run aground is lying”. I’ve run aground plenty but mostly in muddy Chesapeake tributaries, way more forgiving.

Getting to that ledge was fun at least. I was able to sail through some of the islands that I had motored through on the way to Boothbay. 

After crashing on the ledge I very slowly went to the nearest mooring I could get, looked all over the bilge for signs of leaks and then called it a day. 

Harmon harbor

It is Saturday and yesterday I finally made it out of Boothbay. The mechanic, Chris, from Bristol Shipyard, was able to get everything back together. Great guy, A+, 💯, 6-7, etc etc.d

Motored over to Harmon Harbor. Should have sailed some of the way but laziness prevailed. Harmon Harbor is small and quiet, a guy called out to me from his front porch telling me to take one of his moorings, so I did. I will put the mainsail up before leaving this mooring, to ensure that sailing happens today.

Leaving this harbor will be fun, as was entering it. It is a narrow slot with breaking waves on either side. I got to listen to them over night here.

Every time I go in someplace thinking I’ll anchor, I find lots of moorings, floating platforms, etc. I’ve been sailing forever but I am an anchoring neophyte, and this is discouraging. Ah well. Remember stoicism:

Don’t hope that events will turn out the way you want, welcome events in whichever way they happen: this is the path to peace. Epictetus

I’ll be spending at least an hour or two a day the rest of this trip cleaning up after the exhaust leak mess. This Chernobyl is one of the cockpit lockers:

Blech.