season (except for insurance
purposes) does not start in the eastern Caribbean
until mid-August. Before that the storms are generally in the western Caribbean
basin. But with only 2 months before your commitment I would suggest stopping at Luperon, D.R. There is a major ex-pat community of cruisers there who - if you are a compatible person - will look after the boat and dog.
- - Continuing further down island is not a problem after you return. I have left Luperon in mid-May and made it to Grenada
well before mid-August. And that's with several week long stops along the route
in great places.
- - Traveling with a dog requires you have all the medical
records and up to date shots documented. There are several islands which prohibit dogs
from going ashore so you need to be able to deal with that. But there are hundreds of boats who travel with animals
onboard so it is not a major problem, just something to plan and be aware of the requirements. The joy of having the animal with you is well worth the effort.