St Kitts and Nevis have become somewhat friendlier to cruising yachts. Somewhat.
Your itinerary as above covers a lot of moving around and the daily hassle of checking in and out. The big boats use a shore agent to ease the whole operation. (Up to $1,000 per island with fees)
How long do you plan on sailing? Breaking up the daily check in and out would be nice if it were every two or three days
