1. Clothing is critical. On land, I'm a huge fan of cotton clothes. They're soft, comfortable, inexpensive, stretch just enough, and can be pretty durable. However, they have one critical shortfall that makes them far less ideal when on a boat: they hold onto moisture like a sponge. Once cotton gets wet, it stays wet for a long time. And since everything gets wet on a boat on a long passage, this means that if you wear cotton you'll likely be wet all the time. I switched over to various microfiber/polyester/spandex for sailing blends before this trip, and I was quite satisfied. (And dry) But even with quick-drying, moisture-wicking, breathable poly-blends, after 24 hours of wearing the same clothes, especially if you're moving around on deck a lot or otherwise working up a sweat, you'll start getting a little raw in spots. After we arrived in Provincetown, I definitely started noticing this so I picked up some baby powder while we were ashore and, after judicious application to the affected areas, had no more chafing problems. I plan to pack baby powder on overnight passages from now on. And finally, dress in layers. You want to wear the minimal amount of clothing necessary to keep you warm and dry because being hot and sweaty under a too-heavy winter coat will serve you almost as poorly as being cold and wet under a too-light windbreaker. My primary foul weather jacket is windproof and waterproof, thin enough to not be hot in warm weather, but big enough for me to layer up to keep warm if need be. A great combination in my (limited but still growing) experience.
2. Every boat owner should buy a GoPro and a good, sturdy selfie-stick. No, I'm not assuming that all boat owners are vain, selfie-obsessed millennials. Being able to jam a GoPro under water and look at the hull while still on board, or even at dock, makes diagnosing potential problems below the waterline a far easier task. This is especially true if you're in New England without a wetsuit and the water is only 50-ish degrees. Even if you're in the tropics and would love to take a swim in the warm water, you still don't want to go swimming in marina water if you can help it because many places don't bother with holding tanks for their heads. (Yes, they pump their poo straight into the water. Yuck.) In addition, if you need to get a look at something on the other side of that transmission or just beyond where you can reach your head in a lazarette, a GoPro could be very handy as well. Oh, and it's great for taking video and pictures of you actually sailing as well.
3. You can't do it all, so do what you can. On this trip, I was by far the least experienced sailor of the three people aboard. I knew it and they knew it. I didn't try to do anything that was beyond my abilities, and they didn't ask anything of me that I couldn't handle. This meant that I ended up with a lot of seemingly menial tasks like repeatedly stowing and unstowing all of my gear in my berth, tidying up lines when they weren't in use, and crawling around the lazarette to the very stern to inspect some bolts for tightness and leaks. Note, I said "seemingly menial" because in reality each of those tasks was important. My bunk was in the central part of the main salon, so if I hadn't regularly stowed my gear, it would have been all over the place getting in the way and possibly getting damaged. Same with tidying the lines; if we had needed to reef sail in a hurry and our lines had been a tumbled mess, that could have been tragic. And those bolts? They were holding the rudder on and after sailing through rough conditions before arriving in Newport, Beth wanted to be absolutely certain that they were on solidly. By taking care of the little stuff, I freed up Beth and Michael to handle the big stuff. Stuff like plotting our course, navigating us through a few tricky channels, and comforting me as I hurled my guts out over the rail shortly after leaving Newport*. Yeah, that happened.
4. Sleep when you can. When doing overnight sails, you need to set up a watch schedule in advance and stick to it as best you can. For this trip, we settled on 3-hour watches. In anticipation of my watch the night after departing Provincetown, I took a short nap during the day once we were underway. As this was the first night sail for "the new guy", Beth and Michael kindly agreed to stay up with my on my watch from 9-midnight; Beth stayed up for the first half as she was just coming off watch and Michael the second half as he was on after me. After my watch, Beth was still sleeping and the visibility had deteriorated considerably so I stayed up with Michael to serve as a second set of eyes to watch the fog and our sails. I would snooze for 10-15 minutes in the cockpit, poke my head up and look around, check with Michael for anything unusual, then close my eyes again. The nap I had taken earlier proved invaluable at this point. When Beth came on at 3, Michael stayed up with her and I went below to sleep for a few hours. After all was said and done, I had slept about the same amount as I would have in the same period on land, just broken up into multiple smaller segments, so when we arrived in Camden I was wide awake.
5. Modesty on cruising boats isn't really a thing. While some newer boats in the 30-40 foot range will have two or even three enclosed cabins, most older cruising boats that size only have one, and it's usually the V-berth at the head of the boat. Solstice (A Tartan 37) falls into this latter category with an enclosed V-berth forward, three berths in the main cabin, and a double berth (technically a double, but the smallest double I've ever seen) at the port quarter behind the nav station. As the skipper and owner, Beth claimed the enclosed berth forward. Michael took the quarter berth behind the nav station, and I claimed the "pilot's berth" amidships starboard. While my berth was surprisingly comfortable given its small size, it afforded me zero privacy, and neither did Michael's. Changing in the head, while possible, was complicated by its cramped size, especially in rolling seas. Fortunately, while underway there where usually two of us on deck so whoever was below would have the salon to themselves. In spite of this, I'm pretty sure we all saw each other in our skivvies at one point or another, and nobody seemed to mind. We're all grownups, right?
6. Every serious sailor needs a good head lamp. Preferably one with both a red night light and a white spotlight. If you're busy sailing a boat, chances are that you're using both hands for something so having a hands-free source of light in dark environments becomes essential. But a good head lamp is just as useful in the less obvious situations, like when you're hanging upside down in the lazarette trying to grab something at the bottom or reaching around to the side of the engine to check fluid levels.
7. Foulies aren't just for foul weather. A good set of foul weather gear is essential for any sailor for obvious reasons: you can't control the weather and sometimes you it will be cold and rainy. But, in addition to that, foulies are great to wear if you're cleaning the topsides and hosing things off zealously, and if you're feeling the urge to identify yourself as a sailor when you go ashore wearing your foul weather jacket is a sure-fire way to do it.
There is much, much more that I learned that I can't really condense into text, but this was a pretty good summary. I hope you enjoyed reading about it because I certainly enjoyed living it.
* I am 85% convinced that this was the result of me drinking coffee that morning and not purely sea-sickness, but the only way I'll know is to go out again....