I love this question! Do you need to tip everyone associated with pulling off your dream Destination Wedding and if so, how much?
When planning a Destination Wedding, you will most likely work with a wedding planner who is on staff at your host resort. She will likely be the one doing the most work on your behalf. As an employee of the hotel, her services to you are included in wedding package cost so it is difficult to gauge what dollar amount to base your gratuity on. I think any amount up to 5 to 10% of your total wedding package cost is fine.
Florists and other vendors whom you will use, but not necessarily have a personal relationship with, are not expecting a gratuity. Most of the contact with such individuals is made via the Wedding Coordinator.
Photography is a very important part of any wedding and therefore, if you feel your photographer went above and beyond to capture your special day, a gratuity would be welcome. The amount is completely discretionary based on what you feel is appropriate.
If you employ servers to assist with your reception meal, keep in mind that they likely earn very little due to the low wages experienced by most service individuals in the Caribbean. A gratuity would be much appreciated. I suggest $20+ per server, for the meal.
Remember, a few bucks goes a long way in the Caribbean! So if you encounter someone you feel gave you the service you were expecting, it is ok to reward them with a monetary show of your gratitude.