Here's another vote for the offshore route when heading south. Plan a stop in Bermuda...great place to visit and to await a favorable weather window to jump off for the Virgin Islands. Best time to leave: early November.
After you've had your fill of the Eastern Caribbean islands, plan a leisurely trip up through the Bahamas in the spring. This would get you to a jumping off place for the Azores in good time (summer). Having already visited Bermuda, you might choose to go right on past if the weather is right and head for the Azores.