What I did with my summer vacation, Part 3: Sailing Penobscot Bay

The third part of the trip was the part we had been looking forward to for a long time: we would be staying on a sailboat for a few nights.

O'Happy Day

This was the best part of the trip, by far, and everybody had such a blast. I had been waiting for this part of the trip for so long, and it absolutely lived up to the hype and was everything I hoped it would be.

However, I did have a moment of panic when we were on the whale tour. When the sea was at its worst and I thought I was going to have to vomit over the side, I thought, “I cannot handle this for three days. We’ll just have to give up the money we paid and find a hotel room, because I am not putting myself through this, to say nothing of poor Oliver!” Luckily, the sailboat was NOT like that at all. I don’t believe we ever felt seasick at all. In fact, I expected to be rocked to sleep at night, but when we were moored in the harbor you couldn’t really feel any movement at all.

So, part of the reason we found ourselves on a sailboat, in fact, the real reason we found ourselves in Maine at all, was because of a strange little book called Time of Wonder, by Robert McCloskey.

I don’t know how to describe this book. It’s very strange, especially for a children’s book. It’s sort of a “slice of life in Maine” kind of book, very slow paced, somewhat lyrically written. And if that weren’t enough, the entire book is written in second person.

The first time we read it, I didn’t know what to think, but Evie was fairly fascinated. She kept checking it out from the library, over and over again. She just seemed to love it, though we didn’t know why. We tried recommending it to other people, but none of their kids seemed to like it like Evie did. Eventually this led to One Morning in Maine and Blueberries for Sal, but Time of Wonder was really the beloved one (eventually we got our own copy).

We read this book so many times, that we started memorizing a lot of the places mentioned: Bucks Harbor, Islesboro, Hog Island, Pond Island, Spectacle Island, Pumpkin Island, Two Bush Ledge, and Eggemoggin Reach. It really never occurred to us that these were real places, until one day we looked on a map, and low and behold, there they all were! Just like in the book. And at that point we thought, “We could go there.”

This was sort of the genesis of the Maine trip, but we still never thought of chartering a sailboat. But when Sara ran across the listing on airbnb, we knew we had to do it. We contacted them and explained to them about the book, and they were totally on board (no pun intended)! They didn’t think it was silly, and they planned a trip around Penobscot Bay that took us by almost all of the places mentioned in the book.

And the most amazing part? One day we happened to see a beautiful, three-masted schooner. Imagine our surprise when we saw it was Victory Chimes, one of the boats mentioned in the book! It turns out the islands weren’t the only things mentioned in the book that were real. Keep in mind, Time of Wonder was written in 1957; not only was the boat still sailing, but in the entire bay, we happened to see it.

Driving boat

You guys, seriously, this boat was so awesome. The kids loved to drive the boat. When you’re under sail (as opposed to the “iron sail”, a.k.a. the engine), it is so quiet and peaceful. The wind is blowing and you’re gently rocking –it’s very difficult not to fall asleep (at least, Ollie never managed to avoid it). On the other hand, there’s always something to see: beautiful boats, seals, porpoises (even a few bald eagles!) , and everywhere, everywhere, lobster buoys.

Of course when you think of Maine, you think of lobsters. But man, I had no idea of the scope of that. Each fisherman uses their own unique colors on the buoys that mark the locations of their traps. Everywhere you look, it’s buoys of every color of the rainbow, from one horizon to the other.

In addition to the sailing, you have all the little stops on various islands and harbors. Some of the islands only really emerge at low tide, and we did do some more tidepooling. The harbors were fun to explore too; I loved how they were all situated towards the docks, rather than toward land. You would just tie up to the docks, walk up the ramp, use the public restrooms, and then go exploring (i.e. looking for ice cream). There were lots of little shops and restaurants, but also just a lot of small town life. And every once in awhile, some old timer rocking on a porch would give you a little bit of that Maine accent, and it was like walking through a storybook.


Of course, the whole thing could have easily gone the other way. It was really Cap’n Scotty and First Mate Kadee that made the trip. They were both absolutely lovely, especially with the kids. The thing is, when you’re on a boat for a few days with someone, you kind of have to get along with them. The space is pretty intimate; you spend most of your time in a little area about 6′ x 5′. So you get to know people a lot quicker than you would in another setting. So even though we only spent 3 days with them, I really did feel like we became friends.

So much so, in fact, that I felt bad to have them waiting on us hand and foot. It really just felt like we were out for a sail with our friends, so when they would start making food for us and stuff, I felt like I should be pitching in, even though we had essentially paid for it. And the food was actually great. I would say better than I expected, but I’m not sure what I expected exactly. However, it was amazing how much food was stored in that tiny little kitchen! They just kept pulling stuff out of all over the place, and before you knew it, we had a great meal. Evie managed to eat her weight in Annie’s cheddar bunnies every day. We even kept the Sunday pancake tradition alive!

I think it was a little confusing to them that we didn’t really have much interest in learning how to sail. I think most of the people who charter the boat do it because they want to learn how to sail. We were more interested in being on a boat. I mean, maybe we would have had more interest if we weren’t trying to keep two kids happy and not falling in the water, but as it was, we were content to let them do the sailing.

Scotty and Kadee really loved the kids. Some people tolerate kids, and some people pretend to like kids, and some people aren’t pretending. As a parent you can recognize the difference. Also, sometimes adults don’t exactly know how to extract themselves from kids, and the kids therefore demand more and more from them. So I try to be careful to make sure the kids aren’t “trapping” someone who didn’t intend to be sort of consumed by the kids. But in this case, Scotty and Kadee never seemed to run out of patience for the kids, or get tired of them. Kadee made up stories with Evie for at least 2 hours (Evie *never* gets tired of that), and Scotty and Ollie bonded over bedtimes (up to and including Scotty falling asleep with Oliver one night).

bedtime story

There were a couple of particularly noteworthy occurrences.

As I mentioned, Ollie took a nice long nap every afternoon. When you’re sailing, the boat “keels over” (basically leans far to one side), so when he was sleeping below deck on the *very first day* he suddenly went rolling end over end and conked his head hard, right on the floor. He was basically fine, and went right back to sleep. His poor head is basically a battering ram, blasting into things at a fairly regular basis, nevertheless I did feel like a distinctly poor parent.

I know for sure one of Scotty and Kadee’s favorite parts was the sing along lead by Evie. This is a somewhat regular occurrence for us, but strangers are probably not quite as used to it (I guess Evie takes a lot of people by surprise). She knows a LOT of songs, and she lead us in song for a minimum of 30 minutes. Kadee in particular knew a lot of show tunes (including Music Man and Annie, so you know Evie was good to go), and we all sang into the wind at the top of our lungs.

Another fun part was the dingy. When the boat is moored out at a mooring ball, you need a smaller craft to ferry you into the dock. The dingy was essentially an inflatable raft with an outboard motor attached. Compared to the boat it feels crazily unsafe (I kept waiting for one of the kids to fall over the side), but it’s small, fast, and maneuverable. The kids loved it.

Cap’n Scotty kept trying to convince us to take it on our own without him, but I was skeptical. What if I couldn’t get the motor started? More importantly, what if I tied it up at the dock and all the other sailors gathered around to make fun of my knot? Those guys are into knots like you read about, and my Boy Scout days are long behind me. Come to think of it, I couldn’t tie knots even back then.

So I hemmed and hawed until I was absolutely sure I had it all down pat, and even then I waited until we were at some deserted island. The kids were even more unsure than I was. I thought Evie was going to decide not to go with me. But we made it over without incident, and my cleat hitch was so beautiful I took a picture. When we got ready to come back, I got the motor started without incident. Of course, I shouldn’t have worried so much about remembering everything, since I had Evie with me. I gave it a little gas and she said, “Daddy, you’ve got to put the motor in gear first.” I guess I wasn’t the only one paying attention to how it all worked.

For me, the thing I’ll always remember was just sitting on deck with a cozy blanket, watching the ocean. They had about 5 of the coziest blankets you could ever imagine. It was so nice and peaceful, and I think for the first time since I had kids I actually recharged my patience a little bit. When we left I was firmly resolved to maintain my zen state and be a better parent, and I even held on to that for at least a day, maybe even two.

boat by night

Although it was very relaxing, I have to admit that parenting on a boat is a very difficult task. It’s both relaxing and stressful at the same time. I think in general, we’re pretty restrictive parents, which has its pluses and minuses. I know I need to lighten up on the kids, but its easier said than done, especially when they’re walking around on a tiny boat in the middle of the UNFATHOMABLE DEPTHS OF THE OCEAN. I hope we weren’t too restrictive.

In order to keep the peace, we tried to lighten up and give the kids a little head to run with, and Evie in particular took that bit in her mouth and ran with it (wait, change all those horse metaphors to boat ones). When she realized we weren’t going to check her power, she took full advantage, taking charge of all decisions on the boat. Scotty and Kadee were looking for “pirate names” for the kids, and I suggested “Admiral Evie” as an appropriate one – it just seemed to fit somehow.

We managed to keep it to only one drop-down, drag-out screaming fit. Oliver just had a complete meltdown as we entered Camden Harbor, screaming and raging at the top of his lungs the way only a 3 year old can manage. Scotty was doing a bit of tricky navigating through all the boats, and I had to basically physically restrain Ollie below the decks for fifteen minutes or so. It got pretty ugly, and I was both extremely embarrassed about his behavior, and sad that he was so angry and that he was missing all the neat boats. Still, only one in that span of time while being confined to such close quarters was probably not so bad.

Before we knew it, it was time to say goodbye.

Like I said, it felt like we got to know them pretty well in such a short time, and after spending literally every waking minute with them, it did feel sort of odd to be walking away from them. Evie was particularly broken hearted, and had a pretty good cry as we walked up the dock.

saying goodbye

Ultimately, the kids did earn some pirate nicknames – Cheddar Annie for Evie (due to her dual loves of Annie show-tunes and Annie’s brand cheddar bunnies) and Zig Zag for Oliver (due to his…unorthodox boat-driving style).

And thus concludes the best part of our trip. Although it was time to leave Maine, we weren’t quite done with our trip yet…

2 thoughts on “What I did with my summer vacation, Part 3: Sailing Penobscot Bay

  1. Evie and Oliver! Hi guys. It’s Cap’n Scotty. I got up early to watch the sunrise over the Penobscot river this morning. Browsing facebook while waiting for it, I read your fathers blog again. I have tears rolling down my cheeks remembering our time together and realizing how special you two are. Life is such a gift. Live it well! Hugs and kisses from Scotty and Kadee


    • Thanks for your nice comment! This has been on my mind lately as well, because I’m working on putting together the text of this post with the pictures from the trip into a photo book.

      Anyway, thanks again for everything, we had a great time. I read your comment to the kids and Ollie told me a long, rambling story about how Cap’n Scotty fell asleep in his bed because if you pull Cap’n Scotty’s finger he falls asleep. I remembered him saying that at the time, so I guess he still remembers!


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