Hopefully you are doing a sleep aboard the night before you start. We have done five day charters several times. While not ideal its better than staying home. Try this:
Leverick Bay Anegada - lunch at Cow Wreck, dinner at Wonky Dog JVD - Moor in Great Harbour and taxi to Soggy Dollar. Dinner at Foxy's CGB - Dinner at Myetts Norman - Dinner at Pirates