First of all I suggest to organize a one-way trip. In this way you can sail with the right wind and you don't must come back with front wind, that should be strong.
Martinica is perfect for beginning a sailing holiday in Grenadines because it is a french territory, very similar to our condition and it is very close to the best islands in this area.
In particular Le Marin is a good port where to take your boat or catamaran. Here you'll find all you need, like food, spare parts, informations and so on.
What you'll read below is a schematic route that you can follow to have a great cruise in this area. For each step I'll give you some basilar information like distance (NM), route, sea condition and so on.
LE MARIN > MARIGOT BAY (St. Lucia) - 32 NM - big waves between islands
MARIGOT BAY (St. Lucia) > CUMBERLAND BAY (St. Vincent) - 30 NM - big waves between islands
CUMBERLAND BAY (St. Vincent) > BEQUIA - 18 NM - a lot of boats in the bay. buoys by rent
BEQUIA > MUSTIQUE - 12 NM - buoys very expensive, this is vip's island.
MUSTIQUE > MAYREAU - 20 NM - perfect wind
MAYREAU > UNION - 14 NM - good island for food storage and any other necessity
UNION > PETIT ST.VINCENT - 15 NM - private island with a luxury resort
PETIT ST.VINCENT > TOBAGO CAYS - 15 NM - the real paradise
TOBAGO CAYS - CANOUAN - 10 NM - strong wind in front
CANOUAN - ST.VINCENT (Blue Lagoon) - 30 NM