You really can't go wrong either way. It kind of depends whether you want more "civilization" or off the beaten track
anchorages. If you go north to
Martinique, you can visit St Anne, a large anchorage just south of Le Marin. You can then hop up the coast of
Martinique as far as time allows. You will encounter quaint
anchorages that have a more laid back "French
fishing village" feel.
Going south, you can hop down the coast of
St Lucia to the Pitons, beautiful area. Very different feel, more isolated anchorages, better snorkeling/diving. You will encounter "boat boys", usually Rastas who will help you
anchor or pick up a
mooring, get you ice, and try to sell you all kinds of stuff, from fruit/veges, to hand made trinkets. Some people don't like this and feel like they are being hustled. My wife and I embraced them, engaged them, and used their services. Yes, there is a bit of hustle, but so what? We're talking about small amounts of
money, and this is how they make their living. There is a lot of poverty on
St Lucia and St Vincent and some people will not even stop there because of the increase in crime. I personally feel that this .concern is overblown. As long as you use common sense precautions, like hoisting your
dinghy and locking it every night, you should be fine. The other advantage of staying on St Lucia is that you won't have to check in/out of other countries. If you want to have good
internet, pick up a sim card in Rodney bay and
purchase a high speed data plan.
If you like more extended sailing, you can sail down to St Vincent and even to Bequia. If you can do one way, I would
head down to Bequia and maybe even visit
Tobago Cay. The beauty of this area is that you have so many options, you can have a plan A, but easily change to plan B depending on the
weather, sea state, your crew and what you are looking for. We spent two weeks and went from Martinique to
Tobago Cay and back. We stopped at different anchorages on the return trip, so we had a lot of variety. Would do it again in a heartbeat!