A proposed route...

With sailing, plans change with the wind, literally!
We have encountered so many cruisers that have made plans to meet friends and family in certain locations but have been unable to get there in time due to engine / repair issues or just for lack of a weather window.

As such, the best we can do is tell people where we think we will be going to and when and let them decide if they want to be there at a similar time. Fix a firm caveat on that though...we might not ever get there!

The issues with sailing in the Caribbean like many other places in the world is the weather systems. In the Caribbean, we have a good weather window from 1st December to 1st July. Then it becomes hurricane season and not so much fun being in your floating home that moves like a tortoise (relative to a hurricane).
So people tend to 'winter' their boats for hurricane season by pulling them out the water and going back to the US or Europe etc. The Caribbean gets a little quieter during the off season.

As such, our plan, now that we have splashed (yachtie talk for getting the boat into the water), will be to go up the windward islands, then as high up the leeward islands as possible in a 2 month period before turning around and coming south again. It would be good to get to the British Virgin Islands, but it is fairly tight considering we still have a lot of learning to do on the boat and would then need to get her back down to Grenada (ish) by July.

But it is not a race! Sally and I were thinking about going up there quickly and coming down slowly.

Without having given it too much thought, our proposed route is as follows:

Leave Grenada at the end of February
Carriacou for a few days
Union Island
Tobago Cays
Canouan
Mustique
Bequia
St Vincent
St Lucia
Martinique
Dominica
Guadeloupe
Montserrat
St Kitts and Nevis
Anguilla
British Virgin Islands in about end of April (although looking at the above list, we will probably never get there as we are in no rush and want to enjoy all the places we look to sail to)

Whatever we don't see on the way up, we will try see on the way down.

But as with all sailing, this is very weather dependent. If the wind decides to blow in the wrong direction for 2 weeks, we could spend 2 weeks there.

On the way back down, we would like to go to Barbados. I reckon that this will be in about July.

After that...who knows!