Sure - squalls on passage are an issue; they can appear quite quickly and, particularly at night, not be noticed until they are almost upon you.
This subject touches upon another one that is currently active here - the maximum size of boat that a short-handed (or single-handed) crew can handle. There are lots of opinions on that matter but luckily the distances involved in Caribbean sailing are quite short so many of the potential pitfalls discussed there can be avoided.
You need an autopilot
for the longer passages. A radar
is nice-to-have for night sailing in order to detect those nasty squalls when the moon is down or hidden. Harness
& Jacklines are necessary for night sails and recommended for daytime passages - but that would depend upon the size and configuration of the boat. I have in-mast furling
which makes for very easy and quick reefing from the cockpit and I tend to sail under-canvassed even during the since I'm not in a great hurry to get anywhere and prefer safety over speed; I'll always put 2 reefs in sails during night passages.
The waves take a bit of getting used to, but most of the sailing down is with the wind around the beam so the sails will tend to settle the boat rather than make it pitch a lot. I've got the advantage that I started with a biggish boat (43 feet) and went even bigger (now 57 feet), so the boat weighs enough to make for easy and comfortable passages.
I'd love a wind vane, but my sailboats all had sugar scoops which makes for difficult windvane installations - I opt for 2 autopilot
systems instead of losing my bathing/diving area off the back. I'd immediately go for a windvane if I had a boat configuration that allowed it.
The passage from the to St Martin is the longest one at 16-24+ hours, after that all the St. Martin sails are daysails. To get from St. Martin to Ile Fourchue is a couple of hours, from there to the main port in St. Barths is even less. From St. Barths to Statia is a long day's sail, but doable in daylight. From there to St. Kitts Basseterre is a couple of hours, from there to Nevis is a couple of hours. From Nevis to Antigua is a longer sail, but can be done in daylight....
You can see that one can traverse the islands in hops of 20-40nm between anchorages/ports - good distances for a singlehander to deal with even if stuff were to go wrong (the autopilot
dies, sail issues, etc.) and all the ports are well documented in the maps and generally even pretty well lit for night entry/exit. I can't think of another sailing area of that size with so many options and such great weather and water conditions.