I have been sailing "large boats" for approximately 15 years or so now. I have sailed in Galveston through the shipping channel, off the coast of California, I have been offshore from Oxnard to Catalina Island and San Diego. About 8-9 years ago, I moved to S Florida with my wife and young child. We lived aboard and cruised about every inch of land including considerable time in the Tortugas. At this point I have 2 children, Chase is now 8 about to turn 9, Glen is 5. We spend almost every weekend on our Catalina 400 on Lake Texmoa, about 100 yards from where they lay up Valiant Yachts. My parents, who did some cruising with us (especially dad), have purchased a Tayana 42. We work together on both boats, so I can comfortably say that I am as knowledgeable of a Tayana 42 as I am my 400, my 380, and not as much as other boats I have sailed.
My philosophy is safety and "comfort". I do not believe in purchasing every gadget known to man, but I have found many of the modern "gadgets" add a level of safety and comfort which I will not leave home without. I also believe that they have made further destinations/shores within the reach of more people that otherwise might never have considered them.
The items I feel are essential to cruising are:
1) SSB - I have to be able to have some link of communication and be able to get weather information. You lose that about 20-25 miles offshore with only a VHF. Also, the ability to email is a cheap way to stay in touch with family and friends back home.
2) Radar - I doubt there is a piece of equipment on my boat I value more than radar. I remember one time in particular when coming in from Catalina Island and being RUN OVER by all the frieghters. Several changed their course at the last second (or so it appeared to us at the helm). THey are litterally on you in minutes. But even more so, it allows me to see markers when coming into a harbor at night, it allows me to watch for other, smaller boats, it can track the rain storms and how then are moving, and gives you eyes in the fog or when visibility is poor. I would NOT go crusiing without radar unless I never left sight of land.
3) Chartplotter. I MIGHT go cruising without a chartplotter, but it would be out of neccessity. The value in a CP cannot be overestimated. It allows you to consistently know exactly wher eyou are and if nothing else to verify your bearings that you have plotted on paper. It makes night navigation vastly easier and safer. It allows you to set in waypoints arnd areas of danger. It allows you to plot courses to minimize your passages. I do not consider it a toy for those too lazy to plot on paper - nor do I put all my trust in it. I do plot on paper every 30mins offshore. I have had them fail twice on me (once I think to lightning... to be fair). Still, it is a great safety and convenience tool. I agree with those who believe that it is too heavily relied on, but it has many positives which make it pretty hard to leave home for me.
4) Autopilot. If youa re going to do any long distance sailing, I cannot imagine going without a windvane or autopilot (the latter having both its positives and negatives). I believe one of the two is a must. A windvane is prefered by many offshore sailors as it requires no power and does better in storms. The autopilot is preferred by many because it account for XTE and interfaces with a Chartplotter to make passages a breeze. They each have their positives and negatives, not to mention costs.
5) EPIRB. Don't leave home without it.
6) Solar/Wind generation. You are required to run lights at night, your electronics draw considerable power, even the bilge pump will pull 5 amps/day. Since most boats are limited in their capacity to incorporate many batteries (with 2-4-D's being typical), you have about 24-48 hours max without power regeneration of some type. Solar and wind can vastly increase the amount of time away from mechanical power generation. We did not have solar or wind on our 380, but we had a diesel generator. Solar is better - much better.
7) Refrigeration. This is not a necessity. I understand that. But I want to enjoy my time at sea, and not live off of dried foods and can foods. I want to enjoy my time at anchor (where you spend 99% of your time) as the same.
8) Tankage. Lots of it, both water and fuel. Each person must consume in water 1/2 gallon-day in normal circumstances or you will dehydrate. However, when sitting in the hot sun of the tropics or working a winch or doing other strenuous activities, that number will go up considerably. You also have to have some water to cook. You have to have some water to wash your hands before cooking and hopefully after you use the restroom. You have to use your main for power regeneration and to motor through some storms and to get off a lee shore, and to go down the ICW, etc. Tankage has to be a serious concern.
9) Boat. I believe a boat should be comfortable down below. It is your home, not a weekend vacation where roughing it is fine. It has to have a lot of room for storage of goods and spare parts. I believe in a well-performing boat, boat one that can take a beating in the 5% storms you will encounter. We can discuss this in more depth later.
10) Room for a tender. I believe you must have a tender. We ended putting countelss miles on ours. I think the resano for this should be obvious.
This is not my complete list, but it is a start. It gives you a good idea of my philosophies and what I believe a cruiser (especially a circum) should take. I would apprecaite other's thoughts.