That has become our defacto process for route planning on charters. We got into this a little before our first trip to Greece, where a long list of possible ports was developed. When we got there, the wind was very light, and the list had to be scrapped. We won't go as far in high winds either, if there is a chance of any non-beginner friendly conditions.
What we do now is to buy the area guidebook ahead of time, and go over the area around the base at a high level. Then, on arrival at the base we go to the the chart briefing, paper and pencil in hand and take the recommendations from the base. These are often very current, and take into account the weather. We will try to avoid the flotilla routes on the same day due to crowding in smaller ports, but can go to all the same ports in reverse order.
This is how we had one of our most magical experiences ever, a two day stop in Amalfi, Italy, which was not in the brochure, but was suggested by the office at the base, due to the weather conditions being just right. If you set low expectations ahead of time, you won't have sad crew who had their hearts set on a port that was unreachable due to wind, weather and other conditions. And you just might find the experience of a lifetime (which we try to have every year on our charters).
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