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