From Oriental to the Bay is four to five days. I would make it a week and visit a bit each way. Leave the Oriental area mid/late May, spend a month on the Bay and you could be home before serious air conditioning season sets in. If the heat and humidity don't overly bother you stay on the Bay for a couple months. There is enough to keep you occupied for quite a few trips like this and there are towns/anchorages within an easy daysail from each other. There is almost no reason to have top do night sailing unless you want to.