1. Pack light. I've heard this before and I think I did a reasonably good job packing light on clothes, but my camera bag was another story. I brought just the right amount of gear for my Nikon (probably because I don't really have any gear for my Nikon apart from a charger and a pair of lenses), but I totally over-packed on GoPro stuff. My CamelBak had never felt heavy before, but this time it was stuffed to the gills and I definitely felt it. This over-packing was accentuated by the fact that being sick for a few days kept me from doing much of the snorkeling that I had planned on using it for. Urk. One of the first things I did when I got home (aside from sleeping) was cutting down my standard GoPro kit to something more minimalist for future adventures.
2. "Travel Days" are an absolute Godsend. The last time Sara & I sailed in the BVI, we arrived the day before we set sail and we spent that night on the boat. "First night on the boat" is a common service offered by many charter companies, but after a long day traveling, one more night in a real bed, with a real shower in the morning, would have been nice. And on our last day, we had to drop off the boat, clean up, pack up, and make a flight home all in one day. Needless to say, that last day on our last trip was a blur. With these lessons in mind, I scheduled a "travel day" on either end of our charter this time around; we stayed at a hotel at the marina the night before and the night after our charter. Not only did this mean we were far less rushed and much more rested, since our charter company had a busy day scheduled on our return day and we didn't have to catch a flight, they actually gave us a few more hours out on the boat for free. Score!
3. Don't panic! The wind on our third day (leaving Spanish Town for North Sound) was erratic and gusty, so the sail up and around Virgin Gorda was a bit...sporty. Once we cleared Mosquito Island to make our turn south into the Sound, we tacked the boat across the wind (which was out of the ENE). After tacking, the boat refused to point anywhere close to the wind and we were getting heeled over pretty badly. My guess was that we had hit a current that was pushing us off course. After fighting this for a moment there was a loud pop and the helm jerked over away from the wind. We regained some of our pointing ability, but the helm had gotten really sloppy; I would spin one wheel half a turn before the other wheel turned in kind or I felt the rudder engage. Immediately I knew that something in the steering gear had broken fighting that current. I decided to drop sail and motor our way into the Sound. I contemplated breaking out the emergency tiller, but I felt had sufficient helm authority, albeit barely, to navigate the entrance to the Sound. By the time we picked up a mooring ball at the Bitter End Yacht Club, my arms were exhausted and looking back I was surprised by how quickly and calmly I handled the situation. Experience pays! The next day, I found the access panels for the steering gear and, sure enough, one of the pulleys had broken. I called the charter company and they had someone out the next morning to fix it. To Dufour's credit, they engineered their steering system with a particular failure mode in mind (the pulley wheels were plastic, and therefore the weakest link) and ensured that that failure mode was easy to access and repair. Well done!
4. I am not a fan of self-tacking foresails. Our Dufour was equipped with a rather well-thought-out self-tacking foresail system that meant the boat could practically sail itself once you got it underway. Tacking was, as expected, as simple as turning the boat through the wind and both sails simply moved over to the new leeward side. Sailing upwind or on a reach, I rather enjoyed the system, even though it did lose some power because of the smaller foresail required. However, sailing downwind was kind of a pain. It was damned-near-impossible to get the foresail to stay on one side of the boat and it was difficult to trim it properly*. While I appreciated the ease of sailing upwind, during our one downwind leg I wanted nothing more than the conspicuously missing pair of cockpit winches and a few extra lines to get that damned sail set properly. Again, kudos to Dufour for making the best of the design principle (and for making the boat available for sale with a traditional foresail rig), but it's a design principle I'm not personally fond of.
5. Be flexible. Our original plan had been, roughly, to sail from East End to Cooper Island, then to Spanish Town, then to North Sound for at least two days, then to Trellis Bay, then wherever the wind took us (within reason) until we had to get the boat back to East End. Our steering casualty tacked on one day in the North Sound, and me getting sick tacked on another. Even though we spent twice as much time in North Sound as we had originally planned, we still got to Trellis Bay, and actually ended up in a great position to make a beeline back to East End on our last day through choppy seas and gusty wind. Had we been further away, that last day would have been far less pleasant. Having that extra time built into our schedule meant there was virtually no stress added by waiting for repairs or me sleeping a day because the blessed cold meds knocked me out while they worked. While you can do a whole circuit of the BVI in a week, I would recommend doing it in two or only doing a partial circuit in a week. The extra time is worth it, and not hitting two or three stops in one day means the trip won't be a blur for you.
* As much as I present myself as a cruiser, racing sailboats has broken me. I may be okay with meandering wherever the wind may take us, but I want to get there efficiently dammit!