John,
It's about a 500 NM trip, maybe longer, depending on your
route. If you sail non-stop, and average 75% of
hull speed (optimistic!), it's a four day trip at best. It will probably be hard on the
wind until
Guadeloupe.
One of the issues you face if you stop anywhere is the requirement of clearing in through
Customs and Immigration, and then clearing out. The French islands don't seem to mind if you drop
anchor, run up your "Q" flag, spend the night and leave early the next morning without clearance. I believe most of the
English heritage islands will want you to clear in and out. You can generally clear in and out at the same time, as long as you leave within 24 hours, max. The French islands will give you longer, as will
Dominica.
Customs office hours are typically 8 or 8:30 am to 3:30 or 4 pm. Overtime is sometimes available for an extra charge. When you clear in, they will ask you for your clearance papers from your last port of call.
It seems like to me you will have time for only one, maybe two stops along the way. If you go for two, I'd suggest Rodney Bay, St. Lucia as the first. It's a Port of Entry, and you can find a
chandlery, restaurants, bars, a marina,
fuel and
water, and
provisioning there or nearby. Then stop in Prickley Bay,
Grenada, before jumping off for Trinidad. The
passage from
Grenada to Trinidad can be some rough sailing (adverse
current and waves), so keep that in mind. You might average only 3-4 knots over ground on that 90 NM leg.