I have done many gulf stream crossings and have sailed into West End on some of them. The biggest thing you need to watch is weather, because it can get nasty out there on the stream and bigger boats handle nasty better than small. You say you have a lot of time, well, a lot of time to wait out weather doesn't mean you can go either in May or June, but when you are down there in May, you might have to wait a few days or a few weeks for the weather to cooperate before heading across. Provisioning in a small boat is tough because you simply don't have room for a lot of water, fuel and food. Once at West End, you can regroup in the marina there and clear customs, then you should head north around to the Abacos rather than going around the south end. The Abacos offer lots of islands to get out of the weather unlike the Gulf Stream. Returning to Florida might best be accomplished by going south from Marsh Harbour down to Little Harbour cut (spend some time at Pete's Pub) and then sail by the Hole in the Wall towards Nassau. You can cut the trip up by going towards Egg Island and then find an overnight inside the Cays there and then head towards Nassau for some more provisioning. From there you can work your way west to the Berry Islands (more protection and provisioning), then to the NW Providence Channel Light, across the banks to either North Light north of Bimini by way of Mackie Shoals or further south to Cat Cay via Russell Beacon light. Then you can cross the gulf stream again to Florida. Just remember the stream goes north, so if you are heading to Miami, for example, maybe you would prefer to go south more from Bimini/Cat Cay area to say, South Riding Rocks so that you can head in a NW direction. Again, watch the weather every where you go. The Bahamas are not like sailing in the BVI's. There is a lot of open water, lots of weather danger and doing it in a small boat makes you even more vulnerable.