Sounds like a fun adventure you're planning. My two cents of what I would take, if I did this trip, which I have not (hope no one has mentioned these yet, and please correct me if I'm wrong): Lifesling and hauling tackle, re-arming kits for self-inflating PFDs, extra line, duct tape, sea anchor, floating VHF handheld radio, Covid tests, sunscreen, antacids, eyedrops, wool hat, wool socks, synthetic clothes, (I'd leave most cotton clothing home, as even in the tropics hypothermia can happen), replace all nav lights, courtesy flags for countries you're entering, quarantine flag, distress flag, Farady cage for electronics during lightning storms (or use microwave if you have it), pens, pencils, erasers, paper charts as well as electronic ones, fishing tackle. Re-do nonskid on deck. Watch YouTube videos about emergencies at sea. Check the wind frequently beforehand on something like Windy.com so you can learn the wind patterns.
Do a visualization exercise where you ask yourself what you'd do if certain parts on the boat broke. Drill for emergencies. Practice MOB. Trail a polypropylene line behind the boat, maybe with a small float tied to it, in the open ocean in case you fall overboard, if you're solo. Make sure your liferaft certification is current. Add bilge high-water alarms if you need to. Keep boat hull plugs right where you might need them, in compartments, not stored in the back of a locker. Operate with a big safety margin for error. Know what to do if you lose steering. Know where your thru-hulls are and consider replacing them. Consider making a Hudson's Bay start, where you leave in the afternoon, so you can return easily in the morning if you forget anything. Take reading material to take your mind off sailing for a few minutes a day! Have fun.
