We’ve been back in Mattapoisett for a few days, catching up on home projects and savoring memories of our fifteen-day trip to Maine.
God willing, we’ll certainly do this trip again, and hopefully, it will be an annual event. I would also urge other boaters to do it!
With that in mind, I thought I’d write down my big takeaways from this trip while everything was fresh in my head.
Trip Planning
I asked the crew to set aside two weeks to allow me to deal with weather. We ended up taking fifteen days, and that’s about right.
The first port in Maine is Kennebunkport. Its possible to get there in a single day, but it would be a long day – five to six hours. One strategy for us might be to stay in Sandwich or Plymouth the night before we leave to get the Cape Cod Canal behind us.
This year, we lost the first day when we had to stop in Plymouth for electronics repair, which eliminated my plan to reach Wentworth-By-The-Sea on Friday.
I think the key is to give yourself flexibility to ride the wind. Since our prevailing winds are out of the southwest, I’ll plan on covering 80-120 miles a day in the first two days. Likewise, I’ll plan on shorter – 30-50 mile days, coming back into the wind.
The other aspect of trip planning is to decide how long you want to visit each port. We spent six days in Boothbay (due to weather) and two days in three other ports – Kennebunkport, Rockland, and Plymouth.

Vernon and Lynn shared their cruise plan. They generally spend 3-4 days in every port, but they also spend most of the summer on LULU.
I would never abuse a marina’s goodheartedness, but it would make sense to build a trip around locking down two weekends in popular ports and book Friday through Sunday in each port.
Kim (the owner of Boothbay Harbor Marina) told me one of her challenges has been yachts padding their bookings to deal with the weather. Most marinas will refund unused days as long as the yachts show up and stay for some of the booked days. Kim said yachts often book an entire week without intending to stay more than 2-3 nights.
The slip you hold for the weekend will likely be available on Thursday or Sunday night if you need to slide dates due to the weather.

On our 2024 Maine trip, I canceled or rescheduled eight nights due to weather. All were credited or refunded – I did not have to pay any dockage fees.
The Ports
Not all ports are equal. We had no problem spending six days in Boothbay. Kennebunkport, Rockland, and Portland have enough to justify three-night stays.
Wentworth-By-The-Sea is very lovely, but not convenient for visiting Portsmouth. It’s close to the open ocean, has two excellent restaurants on the property, and low fuel costs, making it a great one-night layover port.

Riding a sou’wester from Cape Cod to Wentworth on day one and onto Portland, or even Boothbay on day two, makes a lot of sense.
As a side note, I’d avoid entering Kennebunkport near low tide or Rockland on a Sunday or Monday – when many shops and restaurants are closed.
We visited Camden by bike, not boat. It’s a beautiful little village, but the Lyman Morse Marina is a bit of a hike from town.

We never made it to Coveside or Dolphin, but both look great for a one-night stop. They bracket Boothbay but are both closer to the open ocean.
Marinas
The only marina we’d probably avoid in the future is Dimillo’s in Kennebunkport. Vernon suggested Chicks, and we’ll try that next time.
Safe Harbor Rockland is less than ideal. It’s a ten minute walk to Main Street and Archer’s isn’t a great restaurant. Still, I think it’s better than Lyman-Morse, but if it’s hot, we’ll use the courtesy car to get around.
Be advised that we did not visit Coveside because our onboard water pressure pump was down, and they don’t have water or power on their docks.
Timing
If you followed this year’s daily reports, you know that we had three severe run-ins with fog. Our past trips were later in the season (late July and mid-August), and we never saw a wink of fog.
Fog cannot be predicted accurately, but I think we may try August next time around.
Running Offshore
In 2022, we had two 100+ mile offshore runs; both were in perfect seas.

At the time, the only anxiety came from losing cell coverage 20 miles offshore.
This trip included several runs over 75 miles and one at 125. Three involved an uncomfortable amount of fog (as reported earlier, the 125-mile run from Portland to Plymouth was frightening and exhilarating.)
We could not see land for four of the five-hour trip and couldn’t see the water through the fog for almost an hour.
Running 25 miles offshore is bold, but it has several advantages:
- No Lobster Pots to dodge!
- Virtually no other boats to worry about. And anyone out there likely has AIS.
- Long Period Waves are more comfortable than chop.
We did two long offshore runs into the southwest wind. Thinking ahead, I’ll probably do two long offshore runs with the southwest wind at my back and then crawl back in 30-40 mile legs (subject to change based on wind direction.)
Restaurants
As you may have noticed, we are full-fledged FOODIES. Over the fifteen days at sea, we ate out at least 25 times.
At the end of the trip, while enjoying an incredible meal at Salt, I suggested the crew rank the restaurants. As we started to do it, we realized we were splitting hairs and decided to cluster them instead.
Here goes…
Restaurants We’d Go Out Of Our Way To Visit Again
- Salt – Plymouth
- Ports of Italy – Boothbay
- Coastal Prime – Boothbay
- Wandby – Kennebunk
- Mosaic – Camden
- Thistle Inn – Boothbay
- Surf – Portsmouth
Very Good Restaurants We’d Gladly Revisit
- Batson River – Kennebunkport
- ReelHouse – Marina Bay
- Surfside Smokehouse – Plymouth
- Mine Oyster – Boothbay
- Latitudes – Wentworth-By-The-Sea
Decent Restaurants We’d Possibly Revisit
- East Ender – Portland
- Boathouse – Kennebunkport
- Myrtle Street Tavern – Rockland
Restaurants We’d Avoid If Possible
- 1901 Bar & Grill – Boothbay
- High Tide – Rockland
- Archers By The Sea – Rockland
It wasn’t easy to get into the last group. These are places where two of out three dishes were significantly disappointing and/or the service stunk.
The People
I firmly believe we are all here to spread joy to others and receive joy in return. Spreading joy while boating isn’t very difficult, but it’s so rewarding.
The trip as wonderful, but even more because of all the wonderful people we enjoyed along the way.




















Join Us!
If you’ve read this far, I know you’re a dedicated fan of Buzzards Bay. Let’s talk if you’re considering spending a few weeks in Maine in 2025. I know Mrs. Horne would be more comfortable 25 miles offshore with another boat by our side.
Next Up – Island Progressive

I love following your blog. Now that you’ve visited key Maine ports and restaurants it’s time to see the real Maine. Anchor out behind the many islands and gunk holes. We’ve cruised Maine for the past 35 years and never get tired of its beauty. Buy lobsters from a lobsterman hauling his traps and boil them in sea water. You will be hooked !! You’ll learn to live with lobster buoys and toggles they are not a tremendous menace. Of course you may need to slow down but then again that’s what Maine is all about
Thanks for following our blog. Years ago we sailed with a dingy, anchored, and gunkholed. We no longer have any interest in that side of boating, but please enjoy!
Dave, thanks for all effort you put into these blog posts. I’ve read every one for the last several years and always find them interesting. The Maine series was awesome with such frequent and interesting updates! It was a special treat when we found ourselves (Formula 45 Date Night) docking next to you and Mrs. Horne on Vigilant in Newport of June of 2020! The new boat looks awesome!
I remember that night!
Awesome recap Dave! Too bad I missed you when you were in Portland. Glad you had a awesome Maine Cruise!
-Lauren from Dockwa