Author: Hannah de Regt

Our first stop on the way to Portland was a return to Boothbay where we met up with Russ and Jax after work for what might be our last Maine lobster at the wharf and a return to the waffle ice-cream shop.

Next we headed to The Basin where a former colleague of David’s lived nearby. While I was working, David’s friend took his boat out to meet us and they hung out on the balcony. The weather remained lovely into the early evening, so after work, we pulled out our inflatables and floated behind the boat for a little while!

We arrived in Portland for the weekend. We had made reservations with our usual marina there (South Port Marine), but when we arrived we were told that they would not honor a credit we had for one night due to the fact that “we had changed our reservations too many times” and could not point to any written policy where it said we were not allowed to make advanced changes on our reservations. We were told to either pay or leave, so we picked up our packages and headed across the bay to DiMilos, which is actually more convenient for access to the city anyway. We’ll never stay there again!

David’s hair was getting shaggy so I decided to book us both haircuts for Saturday morning, and after we were leaving we ended up walking through a local arts festival that was taking place in a nearby park! As we were walking back to the boat, we passed by a winery and went in for a wine tasting, not expecting much. In the end, we walked out with two cases (our supply on the boat was running low, and their rose was on super-sale!). In the afternoon, David worked on a boat project – replacing the captain’s chair. We are very excited about this as the old chair had a slight lean to the right, which made it rather uncomfortable.

That evening, we made reservations at Evo, which turned out to be an amazing portuguese restaurant. We sat at the bar that opened into the kitchen and had a tasting menu with wine pairings. The chefs were super friendly and answered questions and chatted with us during the meal. It was a fantastic experience!

On Sunday, I had booked a walking tour of Portland. Our guide was amazing and we learned a ton about the history of the city including the impacts of several large scale fires and the changing demographics. In the afternoon, we did an escape room and had a low-key meal on the boat.

As the work week started, we headed slightly north up to Handy Boat in Falmouth where we would stay for the week and then make our way across the country to Portland, OR for a wedding.

Our flights were early on Thursday, requiring us to wake up at 3am and dinghy to shore in the pouring rain to catch our taxi to the airport. We’d arranged with Handy Boat that they would tow our dinghy back to Highwind for the week, and then tow the dinghy back to the dock on Sunday so that we could return home at midnight!

We arrived in Portland safely and had a fantastic weekend hanging out with David’s friends from college at various pre- and post-wedding events.

We have a GPS tracker on our dinghy, which showed that Handy Boat had moved our dingy back to Highwind on Thursday, but as we were watching on Sunday the dinghy appeared to still be on the boat! We hoped for the best and arrived after midnight back at the boat yard. Luckily the dingy was there and we were able to get back on board where we promptly fell into bed!

After our dinghy adventure back to the boat, David and I decided to stay put in the anchorage for the next day to finish out the work week without moving. Saturday morning, we woke up and cruised to Belfast where the wind was blowing pretty hard as we secured to a mooring in the harbor. We drove the dinghy to pick up Russ and Jax and headed to the brewery in town. When we arrived a band appeared to be setting up for a show.

It turned out to be quite a large band with a variety of instruments including bongos, a violin, and a tenor saxophone. We decided to stay for the beginning of their show and they were very good!

We walked up through the town intending to eat at a local italian restaurant that everyone had recommended, but their wait was too long, so we ended up at a sushi restaurant, sitting at the bar. The sushi was delicious and the bartender was a born and raised local and shared a little of the town’s history with us while we ate.

On Sunday, Jax and I dinghyed to shore with scooters for a grocery run and then we all came back into town later to try the Italian restaurant again. The wait was extremely long again, and in the end, we decided to head back to the boat and I cooked pasta for the 4 of us on Highwind!

Next we headed to Camden, where we planned to stay put for the entire week since David had his long days of quarterly planning. This was a our fist opportunity to receive packages in about a month – so we had quite a few waiting for us when we arrived! We stayed for the first few days on a mooring with the Camden Yacht Club, and then switched half way through the week to a different mooring with Lymen Morse.

Wednesday was our 9th Anniversary and David’s schedule allowed for us to head to town for a dinner celebration. I had made reservations, which was fortuitous since the town was packed with people and most restaurants had a wait!

On Friday, David was finished early and after my meetings ended, we headed to land for an escape room (which unfortunately wasn’t very good) and some amazing Thai food (the best we’ve had in several years) to celebrate the end of a long and busy work week.

The weekend finally arrived and we headed to Rockland to meet up again with Russ and Jax who had discovered that there was a Maine Lobster Festival happening just in town. We ate some delicious lobster for lunch while enjoying some live festival music, and then wandered into town to spend the afternoon at a brewery playing Hanabi!

Russ and Jax had heard from a brewer that the brewery on Monhegan was worth a visit, and a friend of David’s had also told him that Monhegan would be a good stop, so it had been on our radar. This is an island 10 miles south of Port Clyde. The weather was not looking good on Sunday for us to cruise their in our boats, but we discovered that there was a ferry from Port Clyde. With the weather closing in, we decided to return to the boats and do an afternoon cruise to set up in Port Clyde, and then we’d take the ferry to Monhegan the next day. As soon as we pulled out of Rockland, the fog descended and we had an extremely low visibility cruise (maybe only 150ft) all the way to Port Clyde, where the visibility opened up just in time for us to anchor and Russ and Jax to pull up alongside.

The layers of fog made for an atmospheric sunset and we sat on the bows to watch.

The next morning, we dinghyed into town to catch the ferry to Monhegan. The ferry ride was about an hour and we sat on the deck enjoying the warm weather and a perfect breeze. The number of people who live on Monhegan year round is sub-1o0 and the island is mostly hike-able preserved wildlands. There is an excellent museum that covers the history of the island which includes a guided tour of their lighthouse.

After visiting the museum and lighthouse, which had an amazing view over the village, we hiked the width of the island to the cliffs on the other side, which were beautiful. We closed out our visit with beer at the brewery (yes there’s even a brewery on the tiny island) and ice cream.

We returned to the boat in the evening after a wonderful day! With the work week ahead, and some windy days predicted David and I decided to stay put in the anchorage outside of Port Clyde for the beginning of the week when we’ll start making our way west towards Portland.

After Matt and Amy left, we decided to re-connect with Russ and Jax of InQuest, who were heading towards Penobscot Bay. We hadn’t visited much in this area when we were in Maine before and we were only too happy to explore with friends.

Our first stop was Stonington, where we picked up a mooring. David and I worked for the day, and then Russ and Jax picked us up in their dinghy and we went to town for dinner at the local ice-cream place that also served lobster :). David wore his full rain gear, partially as a joke since he’d gotten soaked in the last dinghy ride, but that turned out to be a smart move since as we were about 15 feet away from the dock, a lobster boat drove by at full speed and swamped the dinghy again!

David and Russ had noted that just around the corner from Stonington was a locally famous Portuguese restaurant called the Cockatoo. We decided the next day to head around the corner and anchor in Webb Cove just outside the restaurant for dinner after work. Once again, our amazing friends picked us up in their dinghy to take us to shore. As we neared the restaurant (at low tide) the water shallowed out and we couldn’t see an official place to tie up the boat. There was a washed up dock structure near the restaurant, so we headed towards that. As we approached the dock, we ended up ‘floating’ in about two inches of water and used the paddles to push our way towards the dock gondola-style. I used my splits flexibility to step ashore and pull the boat in the rest of the way. We tied up the boat and used a sketchy looking ladder to climb to land.

The good news was that the tide would be coming up as we ate, so we’d have more water below the boat when we would leave. Adventures in boating! Dinner was excellent.

David and Russ had also independently discovered that also on Deer Isle was a tasting-menu only restaurant called Aragosta. They both tried unsuccessfully to make reservations, but while we were eating at the Cockatoo someone must have cancelled, because we discovered there was an available reservation for 4 for the next night! We booked it.

The next morning, we did another short cruise to Crockett Bay, where we dropped anchor. We were a little nervous since a storm was predicted that night (which was why we decided not to take the two moorings outside the restaurant which were more exposed to the predicted wind direction).

After work, we dressed fancy, then pulled on our full weather gear and hopped in the dinghy to head to shore. We were able to use the bungie anchor to beach the dingy, but Russ’s bow line was not long enough to reach to shore, so David constructed a sand anchor by moving a driftwood log down the beach. The tide was rising, so we knew in an hour or so, we’d have to go out and move the log further up the beach.

Dinner was absolutely excellent. The food was delicious, and they made the necessary accommodations for Russ and Jax who are pescatarians.

David and Russ ducked outside half-way through dinner to check on the dingy and move the driftwood. Just as they were coming back inside, it began to rain and the wind picked up.

We enjoyed the rest of our meal. After we finished, we all changed back into our weather gear and loaded into the dingy. It was quite windy with a good deal of chop in the water.

I took up a spot on the bow to watch out for lobster pots, while Jax held up the light in front of the boat. Meanwhile David used Navionics on his phone to shout directions to Russ in order to navigate us safely out of the cove. I was getting face-shotted with waves up front. Luckily we weren’t going that far, and we got back to the boats safely.

We left Bar Harbor and headed for Southwest Harbor as some more weather was predicted for the week and we wanted to hole up somewhere safe from southwest winds. We ended up anchoring in the next bay north of Southwest Harbor, as we’d spent quite some time in the harbor proper two years ago, and remembered getting waked to hell and back again, so we tried the less-trafficked area just north, and it paid off. Despite several days of high winds, it was our calmest anchorage in months, and the anchor held perfectly through it all.

We had been hanging out nearby because we needed to be somewhere that some friends could meet us by car and hang out for the weekend, so as the winds died down, we made our way into Northeast Harbor once a mooring freed up on Thursday. The little town here is cute and the mooring field has a launch, which made it a great stop to receive the guests. David and I both had extremely busy work weeks, so we basically leave the boat the entire work week until the weekend!

Friday arrived and so did our friends Matt and Amy who were in the area picking up a new car. Matt and David know each other from autocross, but this was actually all of our first time meeting in person. They are a lovely couple with similar nerdy and adventurous spirits as us.

On Saturday, since they had a car, we decided to drive into Acadia and do some hiking. Unfortunately there was no parking at the first hike we tried to do, so we found an alternative option and went up to the “Bubbles”, which miraculously had one spot open up just as we drove by. At the top of the first part of the hike was a huge boulder that appeared to be precariously perched on a ledge, although it is really quite solid.

After returning, sweaty, to the car, we decided to drive to Bar Harbor for lunch where we ate our food in the park overlooking the mooring field where we’d been last weekend! We got some ice-cream and then headed back to Acadia to drive the Park Loop Road one more time and then up Cadillac Mountain. David and I had e-biked up this mountain on our last trip, so I knew the view of Bar Harbor would be good!

We returned to the boat for the evening and taught Matt and Amy to play Hanabi.

On Sunday, we had hoped to take Highwind to Valley Cove – a favourite anchorage of ours in the area, but there were some high overnight winds predicted that would make it precarious to get Matt and Amy back to their car, so we decided instead to take the dinghy all the way there and back and hike from the beach.

Back on the boat for the evening, we played some more games and enjoyed the sunset from the bow of Highwind.

Thanks to Matt for a large portion of these photos from the weekend! We had an amazing time with them and hope that we are able to host them again sometime.

We arrived in Boothbay with plenty of day left for exploring. While we had anchored here on our last visits, we wanted to do everything possible to ensure low movement for Mark’s seasickness, so this time we grabbed a mooring closer in to the harbor. We dinghy’ed to shore, along with the crew of InQuest, and spent the afternoon exploring the town. When David and I were here before, it was the height of Covid, so most places were closed. This time, we enjoyed an afternoon at the brewery, and then walked over the bridge to the other side of the bay to the Lobster Wharf where we ate our first Maine lobstah! We walked back across the bridge and had amazing ice-cream waffle sandwiches before waddling back to the boat for the evening.

The work week started, and David and I settled in to our daily calls. Mark and Robin enjoyed relaxing on the boat. Russ and Jax even offered to dinghy them to shore while we were working and I picked them up after I wrapped up work in the evening. Such lovely friends! The predicted weather rolled in and we did have a little rain, followed by an amazing rainbow.

Later in the week, the weather was nice enough to allow us to cruise again and we headed to North Haven where we dropped anchor. David and I worked while Robin, Mark, Russ, and Jax all explored the tiny town.

On Friday (Robin’s birthday!), we finally made it to Bar Harbor. David and I finished up the work week while the retired folks headed into town. I finished up in time to dinghy in to join Happy Hour before we returned to the boat and got fancy for a lovely dinner birthday celebration for Robin.

On Saturday, we went back into town and took the free bus into Acadia National Park (there’s an amazing free bus system that covers Mount Desert Island and all through the Park). We did a hike which was on mostly paved or gravel path where we could walk holding hands, so Mark was very happy!

We enjoyed having Mark and Robin on the boat for the week, but had to say goodbye on Sunday morning as they began their marathon home from Bar Harbor via airport shuttle, rental car, and flight.

We were invited to join Russ and Jax on a whale watching tour for the morning. Though I had no expectations of the trip, it was actually a lot of fun and I learned a bunch from the naturalist who was narrating the experience. We ended up going 50 miles off shore, and did actually end up seeing whales – a group of 4, 3 adults and a baby. This was apparently the first sighting of so many whales at once for the season, so the naturalist was pretty stoked. Several of them did tail flips as they dove and she was able to identify two of them as known individuals.

In the afternoon, we rented an electric golf cart for a tour of Acadia National Park. It was fun driving around and the views in the park are spectacular.

After Boston, we continued north toward Portsmouth where our early morning cruising is directly into the rising sun, which makes it quite difficult to see and therefore dodge the lobster pots that get denser and denser as we head deeper into Maine. The good news is that we have not seen any fog yet – quite different than our last time here! (Maine is Foggy). We set up on anchor just outside a mooring field since David had been told we were too big to go on any of their moorings. The hold wasn’t great and needed to be reset before we found purchase, but we needed to join our work meetings, so we called it good. At around lunch time, David checked the weather and realized some wind was predicted for overnight, so I called the harbor master and told him we are 50′ (we normally say we are 52′; our boat model is officially a 48′, but the swimstep with the dinghy adds the extra length). He told me we would be able to go on their strongest mooring, 7000lbs of concrete! We moved the 100 yards and felt much better.

After work, Russ and Jax picked us up in their dingy and we headed in to Portsmouth for the evening. We hit some strong currents as we were entering the town harbor and the dinghy got swamped. I had managed to jump to my feet, but David was still sitting down and he got drenched.

In town we had dinner at a brewery while David’s butt dried out and then did a pirate-themed escape room.

The weather did indeed turn and we stayed for another day of rain and wind with evenings on the boat.

For the weekend we headed to Portland where we docked on the t-head just in front of InQuest.

On Saturday, we all took a scooter ride into town where we visited the farmer’s market, had brunch and played Hanabi in a brewery for the afternoon. Sadly we neglected to take photos of any of these activities!

On Saturday evening, Mark and Robin joined us in Portland to visit for the week. They arrived in the evening (after flying in to Boston and taking the Amtrak to Portland) just in time for dinner at a nearby brewery. Though we wanted to spend Sunday visiting in Portland with them, a bunch of wind was predicted starting on Monday for the next few days. Getting to Boothbay and Bar Harbor was a priority for Robin, who grew up visiting these places in the summers and wanted to return, so instead we set sail and made our way east directly to Boothbay to set up on a mooring there for a few days while we rode out the wind.

After finishing work on Friday, we met up with Russ and Jax at a nearby brewery and another Endeavour-owning couple whose boat is named Bella Gato. After dinner back on the boat, I decided that I wanted (finally) to go and see the new Top Gun Maverick movie before we missed the opportunity to see it in a cinema. I found a late night showing at a movie theatre that was just over a mile away from the marina via Google Maps. As we were walking, we passed by a movie theatre that was much closer to the marina!! We are both big fans of the original movie and the new one was excellent – a great blend of gripping action, emotional notes, and call backs to the original.

When we returned to the marina, it was about midnight and there was a young couple with suitcases sitting outside the locked gate to the docks. They made as if to follow us through the gate, but noticed that we were somewhat uncomfortable with letting them in. I asked what was the problem and the guy told us that his dad was waiting for them on a sailboat and must have fallen asleep because he could not be reached by phone. We asked for the name and description of the sailboat and said that we’d go and knock on a window. The marina was HUGE and after about a quarter of a mile walk to the entire other side, we were actually able to locate the boat and wake up the father. We returned back to Highwind and let the couple in to the marina as we passed by the gate – they were very grateful to not have to spend the night outside!

The next morning, we woke up early enough to be able to get to the farmers market in the middle of Boston. We were planning to host dinner on Highwind that night and with the company of vegetarians, I wanted to pick up an assortment of vegetables for a curry. Since we’re really bad tourists, we forgot to take any photos, but the prices in the market were incredible!

We had an absolutely lovely dinner that included homemade Chunky Monkey ice-cream from Jax.

Every evening of the weekend, we were treated to (probably illegal) fireworks from the stern of Highwind across the harbor. These displays included huge fireworks that were essentially launched in quick succession – probably since they wanted to make a quick getaway. One evening, we noticed some debris on fire afterwards and watched them swiftly kick the flames into the water!

The following morning we walked with Russ and Jax to the USS Constitution Museum, where we were able to board the ship that was completed in 1797. It was quite busy, given that it was the holiday weekend, but most of the ship was open for exploration and it was very interesting to walk around.

In the afternoon, we introduced Russ and Jax to the amazingness of escape rooms. We enjoyed the first room so much and after chatting with the owner/game designer regarding our appreciation for the quality of the puzzles/storyline/build that we were convinced to do a second room!

In the evening we had a lovely Italian meal followed by cannolis and pastries from Modern Pastry. This was our opportunity to compare the cannolis against Mikes (these two pastry shops are across from one another and are apparently rivals for the best cannolis in the city), which we had eaten and fondly remembered from our last visit to Boston. The verdict is that Mikes is definitely the winner!!

For the holiday Monday, we didn’t make too many plans. Jax invited me to join her for a mani-pedi in the morning and we had a fun girls-outing. We were re-joined by the boys for a walk to Bunker Hill to see the monument and managed to catch the tail end of a re-enactor discussing the events.

For the evening, we walked north to the marina where Bella Gato was moored which had a fantastic view of the official Boston firework display.

All in all, it was a fantastic holiday weekend!

For the Memorial Day weekend, we had made perfect timing to be able to spend it with David’s family in Rowayton, and we arrived there on Friday. On Saturday, we were welcomed by John and Joan and had a lovely dinner together at their local restaurant – which happened to be the first restaurant we ate at (outdoors) after the Covid quarantine. They were kind enough to give us the use of their car for the weekend to get back and forth between the yacht club where we moored and their house. On Sunday we did a big re-provision and visited Costco for the first time in a year! Sunday night, we headed to John and Joan’s house for dinner and, to our surprise, by David’s cousin Kevin who was in town for the weekend for a bachelor party and had decided to surprise his father for Father’s Day.

On Monday morning, we were joined by Paul and Nancy and all had a lovely brunch aboard Highwind! I made pancakes, waffles, and french toast – it was quite a feast.

With the weather forecast looking good for crossing the sound, we left Rowayton on the holiday Monday and headed towards Greenport, where we planned to meet up with Steve on his boat for the following weekend. As it turned out, he had also used the good weather for the weekend to bring his boat to the area, so on Tuesday after work we were invited to join him and his friends at the house they had rented for a barbecue dinner.

On Friday, with a somewhat light schedule on my part, we were joined in the afternoon by Steve, Lauren, their friends and daughter, plus Nick and his son Noah. Interspersed with a few work calls, we enjoyed the good weather and good company for happy hour before returning to land for dinner.

On Saturday, we pulled anchor and headed to Coecles Harbor on Shelter Island, where we were joined by Steve and Lauren on their boat (1 hour cruise for us, 15 min cruise for them!). It was a beautiful calm bay and very warm, so we enjoyed a swim from the boats and then we ate homemade sourdough pizza.

Lauren and Steve returned back to Greenport in the afternoon and David and I spent a lazy afternoon on the boat – me reading and him coding. A perfect day!

With the Platform secured, and a favorable 2-day weather window, we woke up early and began the first leg of the journey to New York, which is down the Delaware River. Last year, we went from Chesapeake City all the way to the New York harbor in one day, but with diesel prices as high as they are right now, we decided to slow-boat our way north, and planned to break up the journey with a stop in Atlantic City, where neither of us had been before.

We had a pleasant cruise and pulled in to our marina just before sunset. Despite this being something of a last-minute planned adventure, we had made some reservations for a full evening in the city! As soon as we got tied up, we threw on our swim suits and headed to the casino/hotel attached to the marina to their rooftop pool where we had a quick soak in the hot tub with a cocktail. Heading back to the boat, we changed into fancy clothes for the evening. We were headed to a magic show – the Masters of Illusion. I hadn’t seen a magic show live before (not counting a magician at one of my brother’s birthday parties who scarred me for life by sticking swords in my dad’s head in a box). David enjoys watching magic videos on YouTube, but enjoyed the live experience.

After the magic show, we walked to another casino/hotel (on a main road with no sidewalks or shoulder, which wasn’t really advisable), and had delicious Omakase at a sushi restaurant.

It was a lovely evening!

The next day, with the weather holding, we completed the remainder of the New Jersey coastline and pulled into the anchorage we had stayed at last year just north of Ellis Island, with a stunning sunset view of the southern tip of Manhatten.

The next morning, we pulled in to the Brooklyn marina were we planned to stay for the first portion of the week. David would be flying back to Seattle on Monday for a work event and I would remain on the boat and work from my company’s NY HQ. However, we had one day for some tourism and decided to head to Governor’s Island.

When we arrived to the pier, we noticed that we were surrounded by people wearing 1920’s outfits – too many for it to be a coincidence! After a bit of googling, we realized that there was a Jazz Age Garden Party on the island. Once we arrived, we aimed for the visitor center where we could take a free walking tour of the island. We passed by the party where a swing band was playing music for a huge gathering of costumed participants – what fun!

The walking tour took us around the island and we learned a bit about its varied history and ended up on one of the “hills” overlooking Manhatten.

On Monday, David headed to the airport via a piston repair shop to drop off our swim platform pieces in the hopes that a fix/rebuild would not take too long. I commuted to the city via Ferry and had a lovely 3 days working from the office with my colleagues! On Monday evening, we had an ‘executive’ dinner with Steve and Nick overlooking the water on the west side.

On Tuesday, I had managed to get tickets to Hadestown, which I was very excited to see. The musical was amazing – a wonderful blend of storytelling and political commentary, with a timeless quality to the costumes and staging.

On the last night before David came home, we had a big happy hour with almost all of my colleagues who live in the area. I enjoyed all my opportunities for some social time, and especially loved returning to the boat with amazing nighttime city views from the marina. It’s not affordable to stay in the city, but I really appreciate it every time we do – there is so much to experience in New York!

David returned early the next morning and since we were unable to extend our reservation in the marina and needed one more day before we could pick up our rebuilt pistons, we headed north to City Island and picked up a mooring for overnight. The next morning, David went to pick up the pistons, and we headed to Port Washington for the evening. After working, David replaced the pistons and we now have a functioning swim platform!! It does make a lovely whale-singing sound as it is moving, so we think we may need to buy a complete piston replacement, but at least we’ll be able to use the dinghy for the summer. Though it had taken several hours, we hopped in the dinghy and headed to land for a nice dinner to celebrate the milestone.