Leah... I'll say it. You might make it but I think your plan is too ambitious for the time allotted. You have to take into account big wind and seas at that time of year as a distinct possibility that can hang you up for more than one day easily.A lightly built and relatively small Bene is not going to be any fun in those distinctly possible conditions. I would make your plans but also have fall back positions that will still let you enjoy without becoming a slave to an itinerary. May I also suggest that you listen to Chris Parker on SSB receiver each morning or visit his website before you set out so that you know what to expect: www.caribwx.com
which also has the frequencies to listen to.