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Simfr:
Agree that You definitely factor in the Admiral + other guests preferences & dislikes including time/cost getting to/from (ie; flights, connections) charter base.
Do You or your crew like or dislike Open water sailing?..........That has to be factored in as you get away from BVI and head down the chain (or even across to the SVIs). Depending on the time of year & conditions, the Grenadines have a couple of legs albeit short that will seem really long if you do not like open water.
St. Martin - Oyster Pond - (Moorings/Sunsail base) will also be a rude awakening if the wind is up as you are leaving or returning.......plus the sail toward Anquilla.
The Doyle Cruising Guides for Leewards + Windwards will give you a flavor of each island / area.......... on & off the water so you can see if that works for everyone.
For example, Tobago Cays is a beautiful place but if your crew wants a different beach bar & restaurant every night (there are NONE - thus the beach BBQ, but choose carefully)- then they would be disappointed unless you only use as a day stop.
Lots of great places to charter / sail but the Admiral & crew will be the final judges.
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