Jamaica is an easy landfall if you treat it like any other official stop: arrive in daylight, pick a proper port of entry, and keep the paperwork tidy. The only trick is that the nicest bit of water to drop the hook isn’t always the place you’re allowed to do your first round of stamps.
Have your story straight, your copies made, and enough local cash for the small surprises that like to appear when offices are closing or it’s a weekend. Do that, and the rest is just seamanship and patience—same as always.