Margo, there is nothing special about a compressor for a sail boat as opposed to a power boat. Unless the boat has a humungous 220V genset you will want a compressor powered by a gas or Diesel engine. The compressor should weigh about 100 pounds or less and have an output of 3.5-4.0 cfm. If the compressor uses cartridges for the final filter you will want to pick up a half dozen with the basic package, all depending on the length of the trip, of course. Bring gas cans and compressor oil also. Make sure that the unit comes with an intake hose or snorkel as exhaust gas is toxic. Always orient the engine exhaust downwind.
The Alkin is a nice unit but may not be available in the Carribean. The Bauer Junior II, while more expensive, may be the most practical option in that area.
My portable compressor is built up from a military surplus 4 stage Kidde aircraft pump and B&S engine. I was testing it the other day and performance of the carefully rebuilt 40 year old Kidde is still pretty amazing at 4.5 cfm, true FAD, cold fill. (The Kidde is rated 4.0 cfm "minimum"). The entire compressor consisting of full steel crash frame, pump, drive gear, two condenser/filters, 5 hp engine, whip, valves, etc is 85 pounds. I take pride in having the highest output, lightest weight compressor available, and is basically home made, or at least home assembled. Even the expensive Bauer Oceanus, at 110 pounds gross wt and 4.0 cfm cannot match the Kidde performance except when running at 4500 psi continuous, something that portables are seldom used for. Of course, the build-it-yourself route is not for everyone. I'm sure that you will find something suitable for your needs.
One thing I've noticed about the industry. Most mfgrs make outrageous claims about the compressor performance. They either predicate the output on filling an "80" (77.4) tank from 500-3000 psi or tie their performance claim to a hot fill. Bauer does both of these. I own a Bauer Capitano advertised as 5.1 cfm (FAD). I know from testing that number is a hot fill rating. On the same basis, my little Kidde is pumping 4.9 cfm (measured while filling hot tank). That means that the Kidde, at 1/3 the weight of the monster Capitano, is pumping almost as much air. The difference is about 1 minute for filling the average tank. Small high revving compressors like the Kidde are said to have shorter lives. Possibly, but the Kidde was built with cost as no object, these being used in jet aircraft. I know of one that is still pumping with 6000 hours on the clock. However, I would expect average life to be about the same as Bauer, around 2-3000 hours. I'm just rambling. Been working on that hummer since Feb (I work slowly but exceeding carefully, heh), and now it's perfect(famous last words).