Belfast, ME – Friday 9/20 – Bar Harbor Side Trip
Today was the start of a weekend long adventure with Denise’s sister (Claire), her husband (John) and their son (Johnny) and his wife (Scarlett). Our plans included an overnight in Bar Harbor, and then moving the boat south to Rockland. Because of our change to stay in Belfast and not go to Bucksport, we now would meet up with everyone in Bangor. We knew the route well by now, and it was on the way (sort of) to Bar Harbor.
But first we had our own little mini-adventure. Since returning from his business trip on Saturday, Mark has been trying to locate a dry cleaners that would be able to get his “work clothes” cleaned in case he had to go on another client visit. The service in Belfast would not be fast enough to get it done before we were leaving and we didn’t want to wait until we got to Boston as that might be too late. We were successful in finding one in Rockland (where we intend to be on Monday & Tuesday) and they could have it all ready for us by Monday afternoon if we could get it to them by noon on Friday.
So, after picking up the rental car from Enterprise, we first drove the 40 minutes to Rockland to drop off clothes for the cleaners. We then turned around and drove right back through Belfast and on to Bangor to meet with Claire and John (driving) and Johnny & Scarlett (who had flown into Bangor that morning). Here we met at the Bangor Police Department (BPD) to (once again for us) visit the Duck of Justice. For those of you who don’t know, the BPD has a famous Facebook page with nearly 300,000 followers. Office Tim Cotton is the man behind the postings that offer a glimpse into life of the BPD, and the communities around Maine, often with a humorous twist. His posts are legendary and with the Duck of Justice (DOJ) – retrieved from a garbage can a few years ago, he has become a mascot of goodwill and all things positive. The DOJ is now a featured celebrity in the police museum and many stop here daily to have their picture taken with him.

Bangor PD – Duck of Justice
We were lucky in that Officer Cotton was in the office and we had the opportunity to meet him in person. He told us about his upcoming book, his podcasts, and spent some time talking with us about Maine in general. Claire was able to present him with a photo album of her wearing the famous DOJ T-shirt (with the now-famous saying “Keep your hands to yourself, leave other people’s things alone, and be kind to one another”) in all of the half marathons she has walked/run over the last 4 years. It was a terrific time and we had a lot of fun. Thanks TC and BPD!

at Bangor PD with TC
After this excitement, we took the gang to McLaughlin’s Seafood for their first lobster meal in Maine. But this time we went to the McLaughlin’s at the Marina – their nicer restaurant in Hamden overlooking the water. It was a beautiful day and we enjoyed the view and of course the food.
From there we drove to Bar Harbor where we checked into our hotel (Quality Inn) and then Denise & Claire went to pick up their race packets for tomorrow’s Bar Harbor Half Marathon. It was sponsored by the YMCA which is also where the race packet pickup was, as well as where the start and end of the race will be. It was a short walk and after a little window shopping around the Village Green area, they returned to pick up the rest of the clan. Once we were all together, we went to the main shopping area in town and walked down to the harbor where we watched the sun slowly set. It was a beautiful and warm day and there were a lot of people enjoying the view.
From there we went to the Bar Harbor Lobster Company for a delicious dinner on outdoor picnic tables, enjoying the low humidity and delightful weather. It was a great way to end the first day of our adventure.
Belfast, ME – Saturday 9/21 – Bar Harbor Side Trip
For Denise and Claire, the day started with the Bar Harbor Half Marathon. It was a beautiful course through downtown Bar Harbor and then around Eagle Lake and along the carriage trails of Acadia National Park. There were a few small hills and a long climb between miles 6 & 7, but overall it was a terrific race. The best part was ice cream during the after party, especially since it was unseasonably warm. During this time the rest of the clan went to breakfast and then joined the girls for the after party.
Denise & Claire went back to the hotel while Johnny, Scarlett and John went to walk across the shoal to Bar Island, only doable during low tide. They were so impressed they made us all go back there for Claire to see it before leaving Mount Desert Island. Since we had already seen it in 2017 we agreed to stay with the illegally parked cars as there was no parking available near the bar.
We left Mount Desert Island and headed back towards Belfast, stopping in Bucksport for lunch. We discovered the Friars Brewhouse Taproom; a local microbrewery that was run by Franciscan Friars and also known for their bread. Although seating was available, the small kitchen and single cook (Friar) was unable to handle the lunch rush so we were asked to wait in “purgatory” for about 10 minutes. We had no issues with the wait and took in all the sights of the restaurant. It was worth the wait as the food was delicious and filling, and the beer was awesome. Not to mention we all had a wonderful time laughing and enjoying each other’s company.
After lunch we drove our cars back to Belfast by way of the Penobscot Narrows Bridge, and then got Claire, Scarlett & Johnny settled into our boat. The girls and Johnny went to do a little shopping in the stores of downtown Belfast, while John went to look for a hotel room for the night. This was pre planned as we knew there was no way we all would sleep comfortably on our Island Office. (Note: John and Johnny are both over 6’ so they need more than the average space for sleeping). Eventually John found one at a local hotel across the river and came back to retrieve us all just in time for dinner.
We really wanted our guests to experience the quintessential Maine Lobster Pound experience and there is none better than Young’s Lobster Pound in Belfast. It is about 1.5 miles from the marina on the other side of the river. We were able to bring in our own alcoholic beverages and knew enough to bring a (disposable) table cloth as well. Everyone agreed that the food was the best and most affordable meal, and we were treated to an awesome sunset over Belfast Harbor. It was lots of fun and a great way to end a perfect day.
Rockland, ME – Sunday 9/22

Belfast to Rockland
For the first time in 3 weeks, today we would be moving the boat; this time to Rockland. But first we all went (once again) to mass at St Francis of Assisi church. Afterwards, John and Mark returned our rental car to Enterprise while the rest of us got the boat ready for departure. Then before leaving Belfast we needed to get a pump-out, which seemed to take forever. Finally, we (Mark, Denise, Claire, Scarlett & Johnny) were on our way on Island Office, while John drove their rental car to meet us.
It was a nice day to be on the water and our 1+ hour trip was fun. We were able to sit back and relax while Mark drove the boat south to Rockland. On our left was Islesboro Island and on the right we passed the coastal towns of Lincolnville, Camden, and Rockport. Before long we were passing the Samoset Resort on the point at Rockland, and the Rockland Breakwater and Lighthouse.
As we approached the Journey’s End Marina where we had a preassigned slip, we noticed there was a boat in the spot where we were supposed to dock. The marina office is closed on Sundays (after Labor Day) and there was no one around to ask where to go. Since there were several open slips nearby, we took one that was vacant and was a side-tie on the side we had already set up the boat for docking.
Shortly after we settled the boat John arrived with news he found a possible hotel for him to stay in for the night. So he and Claire left to go finalize their stay at the nearby Rockland Harbor Hotel, leaving us some time to chat with Scarlett and Johnny. It was fun to just hang out with these young people and learn of their plans for the future, starting a new job (Johnny) and their desire to buy a sailboat.
When Claire and John returned, we all went to Breakwater Park to walk out to the lighthouse. The entrance is located near the Samoset Resort, but the walk on the breakwater was more treacherous than we anticipated. With the wind and now setting sun, we only made it about a third of the way to the lighthouse before turning back, stopping to take a few pictures along the way.
From there we went to “Claws” for dinner. Of course lobster and lobster rolls are their specialty and we believe they have some of the best in Maine. We sat in their screened porch area and enjoyed a view overlooking Rockland Harbor.
After taking us back to the boat, Claire and John headed to their hotel. This allowed Johnny and Scarlett ample space to spread out their sleeping arrangements, resulting in a good night’s rest by all.
Rockland, ME – Monday 9/23
For Claire and Denise, the morning started with a sunrise run around Rockland Harbor and the houses near downtown.
It also took us past the Sail, Power & Steam Museum, and the Rockland Yacht Club.
Afterwards the sisters went to the Atlantic Bakery Co for a healthy breakfast and coffee.
They then walked to the hotel to pick up the rental car. John had noticed a nail in the tire and rather than deal with the rental car company to repair it, they took it to a local tire company and had it fixed in 30 minutes. Then Claire took Denise back to the boat so both could get showers and get the gang moving on the day’s adventure.
Once back at the marina, Denise noticed the boat had been moved to another slip. Apparently when we came in yesterday, the slip we tied to was a seasonal renter who just happened to be gone. When the marina office opened they wanted us moved, so Mark, Johnny & Scarlett made it happen. It was good experience for these future cruisers.

IO at Journey’s End Marina
Eventually everyone was ready to go and we headed out on the days adventure. First was to go to Owls Head Lighthouse. This is the easternmost point on the mainland that overlooks the western Penobscot Bay. It offers a terrific view, even on a slightly hazy day. We walked up the steps to the top, took some pictures and then went back to the museum and museum shop. On our way back to the car we encountered a group of artists who were getting an instruction by another artist. Johnny provided some humor to the artists when he offered to be their model for the day. It was hilarious!
We had wanted to get a hamburger at the Owls Head Market, where two years ago we enjoyed their super delicious hamburgers. Sadly, we had learned they had closed and the market itself was up for sale. It all worked out ok as none of us were hungry anyway. After we did a quick tour around Owl’s Head Bay we decided to drive up to Camden and show this very touristy, but cute waterfront town to our guests. It was about a 30-minute drive and we arrived to find a parking lot right on the street; something you can never do in the summer months. We walked the short distance to the harbor and walked along the water taking in the scenes including watching the boats queue up at Lyman Morris to be put up for winter storage. Eventually, everyone was hungry and so we went to grab some lunch at Sea Dog Brewing Company.
After some good food, a few beers and lots of laughter, we had to get back on the road. Johnny & Scarlett were flying out of Bangor later in the day and Claire & John would be taking them to the airport. However we first had to return to the boat in Rockland to drop off Denise & Mark, and so the young Rooks could pick up their luggage and goodies they acquired while visiting Maine.
When Claire & John left, Denise & Mark got busy with a few boat chores and business items. When they returned we went to the grocery store and picked up some chicken and other items for a relaxing and delicious dinner on the boat.
We didn’t stay up late as we were all tired and we wanted to get a fairly early start in the morning. We got John and Claire settled into their sleeping arrangements for the night and called it a (very fun) day.
Portland, ME – Tuesday 9/24

Rockland to Portland
Today would be our last day in Maine and we wanted to enjoy the water and coastline as much as possible with Claire. However, it was going to be a bit windy and we wanted to get underway sooner in case things got worse than forecasted. While most of the way we would be in protected waters behind islands, there were several areas where we would be exposed to the wind and waves, and it could make for an uncomfortable ride. With this in mind we left the dock at 8:00 am.
Our plan was to cruise to the Dolphin Marina at Potts Harbor near Harpswell and John would drive the rental car and meet us there. We have stayed here twice before and love the place, especially the restaurant that sits out on the point. This family owned enterprise also houses a lobster pound and a walk up lobster “refresher” that has terrific lobster rolls. But the best thing about the place is the very large blueberry muffins and fresh coffee that is hand delivered to all the boats in the marina every morning.
Once outside the Rockland Harbor we cruised around Owls Head and took the inside route through Owls Head Bay. Here we passed the lobster pounds and houses that we had driven by during our adventure the day before.
We then turned in a more southwestern direction and things got a little bumpy. As we crossed the very open Muscongus Bay and around Pemaquid Point, we rolled with the 2+ foot swells that crashed on our nose. It was just enough to make Claire and Denise a little queasy and not happy. Fortunately, it only lasted about 45 minutes and soon we made our way back behind some of the barrier islands near Boothbay Harbor. We passed along Rams Head Island and its interesting lighthouse.
But we still had to get around Small Point, another area where we would be very exposed. As luck would have it, the swells were less and came from a little bit off our port side (not right on the bow) so the ride was a bit more comfortable. About this time John called to give us a report on the Dolphin marina. Because it was late in the season, the restaurant was only open on weekends now. He loved the marina and surrounding areas (and ate a great lobster roll for lunch at the Lobster Shack), and thought it was a cool place. However, with no restaurant (and our planned dinner for the night) it meant no blueberry muffins in the morning.
With this information, we decided to press on another hour and go all the way to Portland. This would give us a chance to see the city (John & Claire have never been), have more dining choices, and set us up for another run down the Maine coast to New Hampshire while the weather was still good. A phone call later and we had reservations at DiMillo’s Marina, right in the heart of downtown Portland’s “Old Port” neighborhood. Denise plotted a course that took us behind several islands in Casco Bay, and afford Claire an opportunity to see another part of coastal Maine. Mark steered us past Eagle Island, and then through a channel that runs along Peak’s Island and past Fort Gorges, before entering Portland Harbor. Here there were several boats enjoying the harbor and the Norwegian ship “Escape” was docked at the cruise terminal.
Captain Mark negotiated a narrow entry into the marina and docked the boat without issue, despite the narrow fairway. DiMillo’s has a boat brokerage that is a Sabre/Back Cove dealer, and to say we were surrounded by the family of boats is an understatement. However, it is also a well-liked marina by many delivery captains so it was full of larger yachts as well. As we checked into the marina office Claire located John who was trying to find a parking place, which was available right in front of the marina offices.
We then started our adventure walking around the downtown shops near the marina, including on Fore Street. We began contemplating dinner and started asking the locals in some of the shops we went into for recommendations. We were also interested in any rooftop bars where we could get a view of the city from up high. Captain Mark was able to locate a place in the Westin hotel, but it meant walking about a mile to get there. We were all ok to get some exercise, so we made our way along the downtown streets, taking in all the sights along the way. Here are few pictures of what we saw:
Eventually we arrived at the Westin and took the elevator to the top floor. While not a rooftop bar, the indoor bar on the 18th floor afforded us a birds-eye view of downtown Portland. We had a few drinks and an appetizer and enjoyed the terrific views, including watching the “Escape” leave port.
We spent some time discussing where to go to dinner and after receiving a second recommendation for Roma Café, we made a reservation for it on Open Table. We finished our drinks, mapped the route that would take us further away from the boat (but not far), and headed out walking towards the restaurant. Soon we realized we were headed to a local’s joint, and not the touristy places along the waterfront. The buildings were mostly brownstones and the place had a neighborhood feel to it. We arrived at Roma Café and found a delightful relaxed restaurant in an old converted house with very friendly service. The food was delicious and we were so glad we made a reservation, as the place filled up fast with a long wait to get in. If you are in Portland you should try to eat here.
We had also been told of the speakeasy-like bar (Bramhall Pub) that is connected to the restaurant, but the entrance is located at the stairs outside and runs under the restaurant. After dinner we ventured into the place just to have a look around. It is very rustic with the original bricks and beams exposed and is dimly lit (so hard to see in pictures). It had such an old world feel to it that we found intriguing. On another night we may have stayed and had a drink, but we were tired and ready to head back to the boat.
We had considered getting an Uber to take us back to the marina, but decided to walk off our dinner instead. It really wasn’t that far and taking a different path back to the boat we were able to see some pretty cool sites along the way. Most intriguing was the large statue of movie director John Ford; a native from Portland and winner of several Academy Awards – most notably for “Stagecoach”, “Grapes of Wrath” and “The Man Who Shot Liberty Valence”.

John Ford Statue
Once back at the boat we made plans for tomorrow. Again Claire would ride in the boat with us and John would drive in the car. Tonight was our very last night in Maine and we were sad that it was time to leave this wonderful state.
Wentworth by the Sea (WBTS) – New Castle, NH – Wednesday 9/25

Portland to WBTS side trip: Somersworth & Lone Oak
Knowing it would be the last day to have a running partner for a while, Denise and Claire got up for an early morning run before leaving Portland. They headed north from the marina past the cruise ship terminal and saw a new cruise ship approaching into port. They continued along the “rail-trail”; an old rail line converted into a bike and pedestrian path along the water. Here they also passed the Fore Points Marina; a new marina that just opened and was considered but rejected because it does not yet have all its facilities operational. After turning and heading back, they took the path up the hill that ran by neighborhood homes, a condominium complex, and a park. On the way down the hill they encountered a group of young people who were just getting started on their fitness routine for the morning; running up and down the stairs that would lead them down the hill and back to the boat.
Here are some other pictures we took of items in and around Portland:
After returning to the boat and getting some breakfast, we untied the dock lines and headed out of Portland Harbor. Even though it was less than 50 miles to Wentworth by the Sea, we wanted to leave early because we had a full day of activities planned once we arrived. Once again John followed by car as Claire joined us for the cruise south.
It was a nice sunny day with calm seas and few clouds, allowing for some great pictures. We left Portland passing by the Spring Point Ledge Light, Fort Scammel, Ram Island Ledge Light and finally Portland Head Light.
We passed the twin lighthouses at Cape Elizabeth, the Nubble Lighthouse, and eventually the Whaleback Lighthouse at Kittery Point before approaching the entrance into the channel towards Wentworth by the Sea (WBTS) – a Marriott resort.
We chose this location because it was close to Somersworth, NH where our Aunt Judy lives, and who we would be visiting later in the day. Nearly 15 years ago we were here by car and claimed how cool it would be to bring our own boat and stay at this very posh resort. It is quite expensive, but the opportunity presented itself and for a single overnight we decided to splurge a little. After all, our 30th wedding anniversary celebration was uneventful and we figured this was a good substitute.
We arrived at the marina and settled the boat, then we went to the marina office to check in. Here we learned that everything at this resort is extra (pool, gym use, etc.) and since the marina is independently operated, we would get no Marriott points; which we had already expected but felt it didn’t hurt to ask. John was able to find parking near the docks and met us at the boat.

IO at WBTS
Our adventure for the four of us began with a 30 minute drive to Somersworth. We were so happy that Aunt Judy was available as she has been traveling, has more company coming next week, and just completed a major house project that took a lot of time to manage. We visited for a little while getting caught up on life in general and helping her with a few mini projects (Mark & John). We then went on an outing to a local U-Pick farm and market about 20 minutes from her house. Here we purchased some very fresh produce (apples, etc.) and had a great time acting like children and taking pictures of all our fun.
From there we drove to Lone Oak for our dinner and dessert. This is a “refresher” type restaurant that is well-known for its delicious homemade ice cream with outrageously huge serving sizes. However, on Wednesdays they have half priced lobster rolls, which means dinner and dessert could be combined into one stop. Our family has been coming here for years and it never disappoints.
We drove back to Somersworth, said goodbye to Aunt Judy, and then headed back to WBTS for the night. We really enjoyed our time with this wonderful woman and we are so grateful she could spend time with us. It was a perfect day and we had a lot of fun.
Boston, MA – Thursday 9/26

WBTS to Boston
As the sun was coming up, Claire went for a run and Denise went for a walk around the WBTS property. Here are some pictures of this really pretty place:
Today Claire and John would be leaving us; while we move the boat to Boston, they will drive there and see some of the historic sites in town. Afterwards they will head to Cape Cod to spend time with John’s cousins and for Claire to run another Half Marathon on Saturday. So we wished them safe travels and then left for Boston; it was shortly after 8:00 am.

Leaving WBTS
It was a cool sunny and clear day with little wind, so the cruise south was pretty comfortable. However, Denise was worried that after we passed Gloucester the wind was forecasted to pick up and we would be very exposed, resulting in a bumpy ride for the last hour or so of our trip. We did have bailout options, but really wanted to make it all the way into Boston. Our route took us down the coast of Massachusetts to the Annisquam River; an inside route instead of going around Cape Ann and the towns of Rockport (MA) and Gloucester. We had taken this route north on July 4th weekend in 2017 and it was a madhouse, so we were a little weary about taking this very narrow and winding river. However, it was mid-week and way past Labor Day when most recreational boaters are no longer on the water, so Captain Mark felt comfortable with the plan.
Just after passing the Annisquam light, we passed by our friend Liz’s family house where we had a lobster feast in 2017.
We entered Annisquam River to almost no boat traffic and were able to make very good and fast progress. We went under the Route 128 Bridge and passed the Cape Ann Marina (home of tv series “Wicked Tuna”).
Then we entered the Blynman Canal and contacted the Blynman Bridge operator for an opening. This is treacherous area as the current and incoming tide can cause a lot of turbulence, all the while trying to drive between the narrow bridge span. We were grateful there were no other boats coming or going as it gave us maximum maneuverability.

Blynman Bridge
We entered Gloucester Harbor just as the fog was blowing away, which gave Denise some relief. However, the wind was now going to be a factor to kick up the waves for the next segment of our voyage. We left Gloucester Harbor and entered back into the Atlantic Ocean, but skirting the coastline as much as possible. It was a little bumpy as we passed Marblehead, but soon the coastline beyond Boston curved to our left and blocked the wind settling down the seas. Soon we could see the Boston skyline and then entered the North Channel into Boston Harbor. Here there was a dredge operation working and we had to negotiate our way around moving barges and tugs, but Captain Mark did a stellar job doing so.
Finally, we made our way through the harbor and into Constitution Marina; our home for the next few days. We settled the boat and checked in with the marina, picking up our gate keys and getting the internet security codes.

IO at Constitution
Meanwhile, John and Claire (whom we had been in contact with all morning) had been playing tourist in town, and were just finishing walking the Freedom Trail. In the afternoon we caught back up with them and they were able to take us to Costco where we were able to provision the boat. This was our first Costco visit since June and we were so happy to finally be able to buy favorite items that we had missed having on board. They returned us back to the boat and said our final good-bye. We have really enjoyed our time together and we will miss having them around.
Also during the day, we had been in touch with Victoria & Chuck (“Argento”), friends with a BC 37 that we had met in 2017 when we were here. They were making plans to head south to Delray Beach for the winter and were busy readying their boat for their trip. In the afternoon, we finally caught up with Chuck at their boat on “D” dock and discussed our joint plans to leave Boston on Tuesday. The weather until then was forecasted to be sunny, but high winds on Buzzard Bay were going to keep us in port through the weekend. We agreed to keep in touch over the weekend and to cruise together if at all possible.
Meanwhile, the nice morning weather had dissipated and rain was threatening for most of the afternoon. We returned back to our boat just about the time that it did come, and it changed our evening dinner plans. Instead of walking the half mile to the North End, we ate on the boat and stayed in to watch more episodes of Game of Thrones. It was a quiet evening to an otherwise very busy and fun-filled week with family. Unfortunately, it means a long blog post. Hopefully, in the next week we will be able to get caught up and make these smaller and more frequent.
Until then, stay tuned for more of our adventures on Island Office