Just curious BreckSailor, but which route are you planning to Guadeloupe? We did essentially this exact same route with three charter cats in early December but it was over a long week so didn't have much time for exploration unfortunately. 8 weeks is going to be incredible. Were in a hurry on the way down to Deshaies and sailed in the lee of Saba, Statia, St. Kitts and Nevis, Montserrat. Picked up the remaining crew in Deshaies and had day sails on the return trip to Antigua, St. Kitts and St. Barth before crossing the Anegada passage again.

Deshaies was a glorious anchorage - that was my first exposure to the French islands and I think you will find well worth the sail down from Antigua. We didn't have the opportunity to get down to the Iles des Saintes but wished we had. Would love to do just Martinique, Dominica and Guadeloupe on a shorter charter sometime.

Probably obvious but find out what they have aboard for tools and spares. Among three boats on our trip, we had one tool set which were basically toys.

You don't mention which charter company but one thing you have going in your favor if things do go sideways is time - to wait for a part or a mechanic and adjust plans if need be. Our vessels were from the BVI Dream Yacht fleet so we probably could have had some repairs made at Guadeloupe, Antigua or St. Martin but we didn't have time (to wait for a mechanic to drive across the island or to lose a day sailing around to Point a Pitre).

Assume the charter company are allowing night passages? Those were by far my favorite part of the whole trip.