August 26, 2026 Portland, Maine

 Wed.  and Thurs. Aug. 26-27, 2026   Gloucester, MA to Portland, ME   85 miles and 8.9 hours 

Our initial thought was that we'd do a short run up to Portsmouth, grab a mooring ball for the night and continue the next day to Portland.  But the weather models were saying swells offshore would build overnight Wednesday and be very uncomfortable for us on Thursday.  So changed our plans and decided to make it one long day of nice cruising on Wednesday.  That involved an unusual for us 6:30AM departure. Water was pretty calm but definitely swells with a long period, so not noticeable until 9 hours later when we hit land and had the body bobbles where you still are rocking even on solid ground. We stopped in Portland on our Down East loop last year.  Stayed across the river in South Portland.  Opted to stay at DiMillo's Marina in the heart of downtown this time.  Decent enough place but very pricey. I'd rather pay less than half for dockage on the south side and Uber into town. Live and learn!

Very calm day on the open Atlantic.  Running in 200'-300' waters.

Twin lighthouses at Cape Elizabeth built in 1828

Pretty sturdy looking.  Matches the rugged rocky coastline 

Closer to Portland and lobstering activity picked up

Portland Head Light built 1791 is the oldest lighthouse in Maine
and sits at the headlands entrance to Portland

Lighthouses are everywhere here due to unforgiving nature of the rocky coast

Fort Gorges built 1858-1865. Modeled after Ft Sumter. Never saw a battle.

DiMillo's famous restaurant in a converted ferry.

 We got in early enough for a quick walk to find somewhere for drinks and dinner.  Stopped at the Portland Beer Hub for libations and got talking to the bartender for recommendations for "cheap eats".  He pointed us to a local's favorite called Tomaso's Canteen.  Every bit of a dive bar we normally would have avoided at all costs.  But the food was good and very reasonable.  Meaty wings in Thai chile sauce for an appetizer.  Then split a Steak Bomb (think Philly cheese steak).   This put us within a few blocks of Shipyard Brewing Company so.... off we went.  Quite a big facility but split into smaller rooms.  Great logo so had to get one of their shirts. Didn't have a couple beers on tap I wanted to try so got talked into trying their seasonal "Smashed Pumpkin" Imperial Pumpkin Ale.  Would have thought it's to my liking - 10.5% abv and bourbon barrel aged.   Couldn't drink it - nasty stuff.  They had a Hazelnut Porter that was decent - the nose on it was incredible. After all that we stumbled back to the boat pretty exhausted and called it a day.

Touristy town. Old Customs House in background.
Cute historic area, cobblestone streets, lots of shops and restaurants.  

Tourist boat rides around the harbor seem to be a thing. 

Loved the ship weathervane on this building.

Got up Thursday and headed to Standard Bakery for some pastries.  Place gets rave reviews, so not surprised to see a line out the door.  Blueberry scone, Morning sticky buns, Pain au Chocolat.  All outstanding.  Went back Friday for more before we left!  We had intentions of going to the Portland Art Museum but decided we really needed a workday.  Boat is filthy after a couple months on board.  Martha took care of the inside stuff.  I got boat washing detail outside.   By the time we were done nothing left to do but take showers and head out for early dinner. Wound up at Highroller Lobster Company.  Rated as having some of the best lobster rolls in Portland. Place wasn't looking familiar to me (maybe due to recent addition??) but Martha swore we had eaten there.  Checked out the blog from last year and she was right - it's where we ate the day we took an Uber over from the southside.

Line out the door at Standard Bakery. Moved quickly and worth the wait. 

My sistership - the 120' Ocean Alexander Wreckless docked while I was cleaning. 
 Available for sale at $12MM

Congvoyage - a 120' Hargrave makes way down our narrow fairway. No room to
turn around so will need to back out when time to leave. 
Also for sale at a more modest $11MM.

Spent the evening working out possible places we could go to next. Figure it'll mostly be mooring and anchoring around Casco Bay for the next week. Decided to head up the NW shoreline of the bay to Freeport.  Home of L.L. Bean.  

Journey for August 26, 2026