I’ve done a few things to the boat to prepare for this event, although I’m sure there are some things I’ve missed.
Last year I put two set of reef points in the sail. Winds are generally predicted to average between 15 to 20 knots and be steady from the Southeast. Last year however, the winds were light and variable (SE to East). Last year, having not previously using reef points, I reefed the main at the start by tying the reef points tightly to the boom. I could not easily shake out my reefs. This year I added Jiffy reef hardware to the boom for both sets of reef points. This should improve things over last year.
For the jib I’ve rigged a downhaul so as to be able to aid bringing down the jib from the cockpit. I also installed cam cleats on the centerboard trunk since I’ve always found the original style jib sheet cars difficult to work with. I’ll carry the old parts on the boat in case I have to convert back (break something).
Last year I built new hatch covers. I wanted to be able to have hatch covers kept in place in case of capsize so that I wouldn’t lose anything in the cuddy cabin. I hinged them in the middle (across the width) so I could keep the hatch covers on, but be able to easily access the cuddy cabin if needed without removing the hatch covers. To the hatch covers I also added utility bags for my handheld VHF radio, sunscreen, etc. The bags also hold the halyards to keep them out of the way. The hatch cover has mounts for my compass and my main solar panel also. This year I also added collapsible cup holders (for my crew).

Last year I planned to sleep aboard the boat. The cockpit of a DS2 does not have any good way to sleep in as it is. I made some “bed boards” to provide a sleeping platform in the cockpit. The bed board was two 3-foot x 12” boards hinged in the middle with folding legs. When set up it was the same height as the cockpit seats and provided a good sleeping surface. Last year, storage of this item was problem though. This year I plan to camp ashore in a tent, although I will still carry the boards. For storage of the boards this year I added strap attachment points in the stern to strap the boards in place similar to the rear deck on a DS1. A slight modification to the boards has allowed me to add a second solar panel with small rechargeable battery to run a small electric cooler. The small cooler is to provide something cold when we get into camp at night for my cousin. I live in Texas and I’m used to the heat, he’s from Wisconsin and I’m not sure he will as well, got to keep the crew happy. I’m trying to better distribute the weight in the boat this year. Last year I was a little bow heavy with everything in the cuddy cabin.

I added oars to the boat last year because I didn’t want to carry a motor and gas. I put two inspection ports in the side rails to install the oar locks. The boat rows well with the centerboard down a little. I also have a topping lift to keep the boom off my head. My rowing seat (1” thick board) stows nicely on its’ side in the stern jammed in the cockpit drainage channel. The space in the side rails which I can access through the inspection ports I’m going to store my old set of stays, spare line, and hardware & tools in bags. This will provide an easier place to get at these things instead of digging thru stuff in the cuddy cabin if needed.

My fenders for tying up at docks I’m going to carry along the sides of the boat. I also want to be able to use the lines attached to the fenders as “rescue” lines in case of capsize (which I don’t want to happen).
One of the big problems I have is where to carry all the water. It is recommended to carry one gallon of water per person per day. That means for the two of us we are going to need at least 12 gallons of water. We are going to carry 2 additional gallons as well. There may be places along the way to refill, but we can’t count on it. To help distribute all this water on the boat I added two 6” inspection ports in the cuddy cabin floor. I plan to store some water in the inner hull. I have a bag that I will secure between the mast step and the centerboard trunk. I added strap attachment points on the underside of the cuddy floor. I want to make sure this load doesn’t shift. I also bought two cheap folding chairs ($5) for their nylon bags to store some water along the centerboard trunk. These bags will also be secured. The flotation down there will also help keep it in place. By storing some water low in the boat, I’m hoping to provide ballast and a lower center of gravity. I think that perhaps the DS1 is better suited to storage of equipment due to being able to store it lower in the boat.
As far as food goes, most of what we are taking does not need to be kept cold. I don’t know if we will have ice after Day 2. We may find ice along the way, but I don’t know. Any food we take that needs to be kept cold will be used at the beginning of the trip.
That's about, I know I forgot something.
John