Wow, I think no one has responded yet as your question is just too broad.. Are you going to be staying over night on the boat or staying on land? There are not a lot of sailors on here, so logistics for getting places from a sailing perspective will be difficult for most of us.
For one thing, the trip is not a quick hop, it's 90-ish miles, and often bumpy. You'll be on a nice beam reach both down and up, but it's a bit of a haul.
It is not often a reach. The trip can be a nasty beat upwind, most do it as an overnight to arrive in daylight. Marigot is the closest anchorage. Simpson Bay lagoon is probably the largest concentration of yachts in de ilons. This forum will tell you everything you need to know about what to do onshore.
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