Our first is advice is to JUST DO IT! If you can make it happen, do so. There's nothing else like it! The freedom to go where ever you like, and stay as long as you like, to do whatever YOU want to do on any given day is just incredible. It's not stress free, but it's a different kind of stress. YOU are in charge of your own little floating world. It's an incredible and awesome adventure!
The most important equipment are the things that keep the boat afloat and sailing. Make sure your rigging, both standing and running, is sound. We replaced all of our rigging before we left, and our standing rigging was upsized one size for offshore. We had brand new heavy duty sails cut--also for offshore sailing. We made sure all our through-hulls and plumbing below the water line was in good shape, and old hose clamps were replaced with stainless AWABs. After that, it's up to you as to how much equipment you'd like aboard. Items I would not leave home without include autopilot, chartplotter/GPS, radar, and refrigeration. We wanted our cruising experience to be as comfortable and safe as possible, so we tended to go all out. Here's a sampling of some of the equipment we had aboard and how it worked for us.
Autopilot: Go bigger! We initially installed a Raymarine ST5000 below decks, linear drive autopilot, which was a little overkill for our size boat. It started giving out half way down the ICW. Raymarine upgraded us to an ST6001+ while we were down in Florida, and we are very happy with it! The weak link in the chain is the ST600R Remote unit. We are on our fourth one in 3 years, all replaced under warranty. They keep overheating! The warranty is expired now, and our present one is starting to overheat.
Refrigeration: Unless you're really cruising on a shoestring, this is a must. We have a Seafrost double plate with redundant engine driven and 12V systems. It really worked well for us, and we were very happy with it. We charged it for 45 minutes everyday while we charged our batteries, then ran then turned on the 12V in the evening. We didn't have a freezer per se, but anything put right under the plates stayed frozen. We knew a lot of people with much cheaper Adler-Barbour 12V systems who were happy as well. In fact, we never heard anyone complain about their refrigeration.
Water Maker: In the interest of keeping things small and simple, we went with the Katadyn-40E water maker. It made fantastic water when it was working. The trouble is, it would work for about 6 weeks, then break. The Katadyn service department was very friendly and helpful, but it got old having to send the pump back every couple of months for service--not an easy thing to do when you're in the Caribbean. We had friends with much more expensive and more complicated systems who were very pleased with them. If we had it to do over again and unlimited funds, we would go with one of these. Can you live without a water maker? Yes, and despite having to pay for water in the Caribbean, it would probably be cheaper. However, being able to make your own water makes you that much more self sufficient, and not having to lug heavy water jugs is a big plus. Keep in mind that, during the rainy season, a good rain collection system can keep you supplied with all the water you need.
Anchors: We had a 35lb CQR at home in Long Island Sound that worked great for us. For the trip, we decided to oversize a bit, and the cheapest way to do that was to get a Bruce 44. The Bruce did very well by us. We dragged anchor only 3 times in our 21 month journey, and all of those were when we tried to set it in grass. Our back-up Spade anchor (20lb aluminum) also set quickly and held very well every time we used it. Our primary anchor had 200 feet of chain and 100 feet of rope. We only got into the rope twice during the trip. We also carried a Fortress FX-37 storm anchor, but we never had to use it.
Mainsail: We LOVE our Schaeffer in-boom furler. When we were out in the middle of the ocean at night in a storm, it was a great comfort to be able to reef the sail from the cockpit. We also didn't have lazy jacks to get caught up in the sail, and the sail cover was a breeze to put on. We used a cordless high torque Milwaukee right-angle drill with a "Winch Bit" to raise and lower the sail. This cost us about $350 versus the $3K it would cost for an electric winch. We did have some problems with the system, as we were the first to actually sail with one down in the Caribbean. When we were in the Virgin Islands, the extreme heat caused our mast track to stretch and jam into the feeder. We remedied this by cutting off a portion of the track. Schaeffer customer service has been very good to us. When we had a problem on the return trip raising the sail, due to a cracked mast track, they paid a rigger in the USVI to come to our boat and fix the problem. In hindsight, we wish we would have put the money into repowering the boat (given all the engine problems we had) and gone with a Doyle StackPack--not quite as clean and convenient, but very functional.
Energy: We have all gel cell batteries for the safety and lack of maintenance issue. The house battery bank consists of three 8D batteries (660AHr), and a separate starting battery bank has two Group 27s. We monitored the batteries very closely with a Link 2000 battery monitor--never letting the battery banks get below 50%. They've been aboard for 3 years and are still going strong. In retrospect, we could have probably gotten by with only 440AHr house bank. However, the larger bank came in handy when we were out at sea for 4 days without an engine! We had no generator, but we had a Rutland 913 wind vane and an 80W solar panel. Between them we got about 50AHr per day. We probably used about 150AHr per day, and only had to run our engine (with it's 110A high output alternator) for about 45 minutes every day. Without the wind and solar power (and the 12V refrigeration), we would have had to run the engine twice a day. We had a Heart 1500W inverter for AC power, which we only turned on when needed.
Communications: We had an Icom M802 Marine SSB radio aboard, and were very glad we did. While propagation was not always great, it was our primary source of weather and allowed us to stay in touch with other distant cruiser friends. We never used it for email, but a number of people we met use Winlink (which is free if you have a general class HAM license) or SailMail via the SSB for their email. We used our GlobalStar satellite phone for email, for phone calls, and for very slow (56Kps) surfing of the web if needed. For the most part, it worked very well, although sometimes we had to wait a few minutes to get a good signal. However, if you're going beyond the Caribbean, you need and Irridium sat phone. It is the only one that has global coverage, but if you need to access the internet, it's way too slow. We also had an unlocked GSM cell phone, which came in very handy. The US-based number we had only worked in the USVI, Puerto Rico, and the U.S. However, cards could be purchased in different countries that would give you a local phone number. However, the cards were costly.
Navigation: We have a Raymarine color chartplotter, that takes C-maps, which we LOVE. It was supplemented with Raymarine Navigator which we ran on our Panasonic Toughbook at the nav station. The chartplotter and computer were connected via a hsb2 cable. If we were on a long passage or had a complicated route to follow, we would plot the route on the computer. Raymarine Navigator is not the most intuitive piece of navigation software out there, but it is very powerful and interfaced well with all our Raymarine instruments. Even when we were navigating by the chartplotter, we ALWAYS had paper charts out and would make frequent use of them to confirm the C-map. For instance, once we were heading straight for a reef with only 3 feet of depth that did not show up at all on the C-map. It was charted on the paper chart, however, and we safely avoided it. In our experience, the quality of C-maps varies widely with region. In the US and US territories, it is generally very good (although that reef was south of Puerto Rico). In the event that our chartplotter failed (which it never did), we carried two handheld GPS's aboard as well (one was kept in our ditch bag). Finally, we both learned celestial navigation and carried a sextant and all the required tables, in case we lost our GPS out at sea.
Radar: We have a Raymarine radar that is read on our chartplotter. It is mounted on our mast on a gimbal, which gives us a good range even when the boat is heeled over. It is a tremendous help at night and in the fog.
Safety: Safety was very big with us, and we had every piece of safety equipment we could think of. In addition to equipment, we had all of our lines lead back to the cockpit, so we could raise, lower, and reef the mainsail and genoa without going out on deck. We both had harnesses with auto-inflate life jackets (complete with whistles, strobe lights, and sharp knives), and straps to connect ourselves to the boat at all times when we were offshore. One-inch yellow webbed jacklines were run the entire length of the boat, so we could stay attached if we had to go up on deck. In case of a POB, we had an inflatable MOM-8 mounted on our stern rail, as well as a low tech Life Sling, in case the MOM-8 failed to deploy. We carried a drogue (for slowing down the boat while surfing down waves in heavy seas) and a sea anchor (to help keep the boat hove to in really bad conditions). Our life raft was a brand new 6-man Winslow Ocean Rescue, for which we paid a lot of money. However, we felt good having it aboard. It was stored in a soft pack in the rope locker in the cockpit. If we had it to do over again, we would probably purchase a good quality used life raft to save some money. In our ditch bag, we carried a G-PIRB and a hand-held GPS that attached to it, a VHF, personal items (like medication, ID, and glasses), a lot of batteries in a Pelican case, and the usual safety items, such as signal mirror, flares, etc. Luckily, aside from the harnesses and life jackets, we never had to use any of it. A big part of keeping safe for us was monitoring the weather situation. We tried to be fair weather sailors as much as we could, but inevitably got caught in some nasty conditions. In the Bahamas and Caribbean, we subscribed to Chris Parker at the Caribbean weather center. Primarily, we would listen to his forecast on the SSB and then talk to him and get our specific forecast, which was extremely helpful. We also signed up for his email forecasts, so we had something, even if SSB propagation was bad that day.
Tools: You can never have too many tools aboard a boat. We had an extensive tool box with everything we needed to work on the engine, as well as plumbing, electrical, fiberglass, and wood projects. We carried a lot of spare parts including engine parts (we bought the extended cruising spare parts kit for our Westerbeke 50 and used nearly everything in it), plumbing parts, electrical connectors (heat shrink), fuses, wire, pieces of wood, and a large selection of stainless fasteners. For power tools, we had a grinder, both regular and right angle drills, a buffer, a sabre saw, a dremel tool, and a palm sander. We also had a small vise onboard.
For boat insurance, the first year, we went with Blue Water Insurance. It was very expensive, and we had to pay the annual premium up front, before they would consider the application. On the plus side, they were easy to communicate with via email. When we heard about another boat insurance company that was taking people's money and making up a fictional underwriter, we decided to look into our underwriter. We could find no evidence of the existence of the company on the internet, so we wrote to Blue Water. We received back and indignant email, saying that they've been insuring boats for years, and blah blah blah, but nothing to reassure us that our underwriter was real. There wasn't much we could do from the Bahamas, so we let it go. Luckily, we never had to make a claim, so we still don't know to this day if we were actually insured. This year, we went with IMIS (International Marine Insurance Services) and are very pleased so far. Our premium, for the same coverage, is almost half what we were paying Blue Water. They were very reasonable and easy to deal with. We accomplished the whole transaction via email and FedEx from Bequia.
For health insurance, we went with SRI through Blue Water Insurance. It is a catastrophic policy with a $5000 deductible and very reasonably priced. Communication via email is excellent and very professional. Fortunately, we haven't had to make a claim, but so far, we're very happy with it.
Our budget was $3000 a month, which was about midrange for cruising budgets. Some months, when we had mechanical problems, we would spend over $5000. Other months, we would spend only $1500. It was variable, depending on our location and the mechanical state of the boat. In the end, you spend what you have. It can be done very inexpensively, if you are willing to sacrifice some things.
Never try to run from an approaching hurricane. There is no way to accurately forecast the eventual track of the hurricane. So our advice is to get the boat to closest safe harbor--preferably with a mangrove swamp--three days before the hurricane is due to arrive. It will take that long to properly secure the boat. We were in Nevis when we heard that Hurricane Emily was approaching and decided to make a run for it down to Grenada. We had three days until she was supposed to make landfall in the Eastern Caribbean. Bad Choice! Even if we had made it to Grenada, over which Emily eventually ended up tracking, we wouldn't have had time to properly secure the boat. Luckily, we had a fuel leak which prompted us to turn in to Rodney Bay in St. Lucia, and we only caught the edge of the storm.