Jeremy,

The southbound legs are a fun sail.

The northbound legs from Canouan to Bequia, Bequia to St Vincent, and the northern end of St. Vincent to St. Lucia will be similar to going from Grenada to Carriacou. This can be an upwind slog especially if the wind is from the NE and you have to make multiple tacks.

Depending on how far south you wish to go (Union?), a start/stop in St. Lucia can be ambitious for 7 days. I would suggest either a 10 day charter, start/stop from St. Vincent (Barefoot, DYC or Horizon), or a one way. DYC may also allow you to drop off in St. Vincent if you wish to start in St. Lucia. We have used Barefoot 5 times with good experiences. They also have brought on some newer boats recently as their fleet was a bit long in the tooth. We have found that the best way (most reliable) to get to St. Vincent is via BGI on SVG Air. It is a bit pricey, but the peace of mind as compared to Liat is worth it for us.

We are planning a 10 day start/stop from St.Vincent later this year, and did a one way St. Vincent to Grenada last year.