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!