I normally prepared the first two main meals at home and then reheated it. It stayed perfectly cold in the coolers. Braised chicken or short ribs were always a favorite because they get better after a day or so. Chicken Marbella was also common. I also almost always brought along a batch of marinated grilled veggies. We ate them as sandwiches, side dishes and used them in frittatas.
Does the boat have a rail grill? We almost always used the grill for the main meal. I liked to pack frozen meat (steaks, marinated chops, chicken, fish) some of which had been marinated before freezing. The frozen meat keeps the coolers cold! If you don't have a grill I would suggest you freeze smaller cuts of meat (boneless skinless chicken breasts & thighs, skirt steak, fish, blocks of shrimp, etc.) because they can be cooked in the galley much quicker than a steak or chop. Leftover meat along with some fresh veggies/fruit can easily be turned into great lunches (salads, tacos & sandwiches).
For really easy meals you could even bring prepared frozen taco meat, frozen Italian beef from your favoite place, sloppy joes, etc. along with the chili. That would leave you more time to sail and less time in the galley.
For grains I preferred to prepare quinoa, couscous or rice instead of pasta. It's amazing how quickly a pot of water heats up the galley and how dangerous it can be on a sailboat.
Frittatas, Italian tuna, salame and other cold cuts are great for lunches. GORP (good old raisins and peanuts and M&Ms) makes for great snacks as does fresh fruit and veggies. Also a stash of meal replacement bars might come in handy.
Don't forget to pack a couple of sharp knives, various seasoning, a couple hot pads, a slew of paper towels, small cutting board, etc.
Most importantly don't forget to bring along several bottle of Mount Gay!