How it works: dates selection

Your travelling dates for your kitesurfing trip are known and not flexible

If your travelling dates are known and you only have specific dates to do your Caribbean kite cruise, then choose the "known dates" search engine: only the cruises matching the exact dates you've entered (departure and return) will appear in the results.

Your travelling dates for your kitesurfing trip are flexible 

If your travelling dates are flexible and you can go anytime, for a certain duration, between certain dates -and you just haven't decided exactly when-, then choose the "flexible dates" search engine: you can enter your first and last availability dates and choose your desired length of cruise.
The results will then show all the cruises of your desired length of time that can take place during your availability window.